Fare Guide

Estimated lowest fares found within 7 days

Cheapest Airline Frontier Airlines

The cheapest airline(s) flying from Boston to Chicago is Frontier Airlines.

  • Frontier Airlines Frontier Airlines
  • JetBlue Airways JetBlue Airways
  • United Airlines United Airlines
  • American Airlines American Airlines
  • Southwest Airlines Southwest Airlines
  • Spirit Airlines Spirit Airlines
Cheapest Month January

Travel Period: January 2025 - December 2025

The cheapest month(s) to fly from Boston to Chicago is January.

  • Jan 2025
  • Feb 2025
  • Mar 2025
  • Apr 2025
  • May 2025
  • Jun 2025
  • Jul 2025
  • Aug 2025
  • Sep 2025
  • Oct 2025
  • Nov 2025
  • Dec 2025
Cheapest Day of the Week Thursday

The cheapest day(s) of the week to fly from Boston to Chicago is Thursday.

  • Sun Sunday
  • Mon Monday
  • Tue Tuesday
  • Wed Wednesday
  • Thu Thursday
  • Fri Friday
  • Sat Saturday

Flight Schedules

Last Updated: Mon, 2 Dec, 2024

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    • Airline Filter by Airline
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      • Availability
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • 19:55 BOS
        21:40 MDW
        2Hrs, 45m Direct
      • BOSBoston Logan International Airport 19:55 - MDW 21:40 2h 45m Direct
      • BOSBoston Logan International Airport 19:55
      • MDWChicago Midway Airport 21:40
      • 2h 45m
      • Direct
      • Southwest Airlines (WN 3586)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 3586)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 20:00 BOS
        21:45 MDW
        2Hrs, 45m Direct
      • BOSBoston Logan International Airport 20:00 - MDW 21:45 2h 45m Direct
      • BOSBoston Logan International Airport 20:00
      • MDWChicago Midway Airport 21:45
      • 2h 45m
      • Direct
      • Southwest Airlines (WN 4580)Boeing 737 800
      • Southwest Airlines (WN 4580)
        • -
        • -
        • -
        • -
        • F
        • -
        • S
      • Boeing 737 800
      • 20:15 BOS
        22:00 MDW
        2Hrs, 45m Direct
      • BOSBoston Logan International Airport 20:15 - MDW 22:00 2h 45m Direct
      • BOSBoston Logan International Airport 20:15
      • MDWChicago Midway Airport 22:00
      • 2h 45m
      • Direct
      • Southwest Airlines (WN 1182)Boeing 737 800
      • Southwest Airlines (WN 1182)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 800
      • 05:00 BOS
        07:04 ORD
        3Hrs, 04m Direct
      • BOSBoston Logan International Airport 05:00 - ORD 07:04 3h 04m Direct
      • BOSBoston Logan International Airport 05:00
      • ORDChicago O'Hare International Airport 07:04
      • 3h 04m
      • Direct
      • American Airlines (AA 3790)Embraer Emb 175
      • American Airlines (AA 3790)
        • -
        • -
        • -
        • T
        • F
        • S
        • S
      • Embraer Emb 175
      • 05:10 BOS
        07:16 ORD
        3Hrs, 06m Direct
      • BOSBoston Logan International Airport 05:10 - ORD 07:16 3h 06m Direct
      • BOSBoston Logan International Airport 05:10
      • ORDChicago O'Hare International Airport 07:16
      • 3h 06m
      • Direct
      • American Airlines (AA 3493)Embraer Emb 175
      • American Airlines (AA 3493)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • Embraer Emb 175
      • 05:10 BOS
        07:00 MDW
        2Hrs, 50m Direct
      • BOSBoston Logan International Airport 05:10 - MDW 07:00 2h 50m Direct
      • BOSBoston Logan International Airport 05:10
      • MDWChicago Midway Airport 07:00
      • 2h 50m
      • Direct
      • Southwest Airlines (WN 787)Boeing 737 700
      • Southwest Airlines (WN 787)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 700
      • 06:00 BOS
        08:07 ORD
        3Hrs, 07m Direct
      • BOSBoston Logan International Airport 06:00 - ORD 08:07 3h 07m Direct
      • BOSBoston Logan International Airport 06:00
      • ORDChicago O'Hare International Airport 08:07
      • 3h 07m
      • Direct
      • JetBlue Airways (B6 311)Embraer Emb E90
      • JetBlue Airways (B6 311)
        • -
        • -
        • -
        • T
        • F
        • S
        • S
      • Embraer Emb E90
      • 06:00 BOS
        07:56 ORD
        2Hrs, 56m Direct
      • BOSBoston Logan International Airport 06:00 - ORD 07:56 2h 56m Direct
      • BOSBoston Logan International Airport 06:00
      • ORDChicago O'Hare International Airport 07:56
      • 2h 56m
      • Direct
      • United Airlines (UA 1414)Airbus A321 Neo
      • United Airlines (UA 1414)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • Airbus A321 Neo
      • 06:00 BOS
        08:06 ORD
        3Hrs, 06m Direct
      • BOSBoston Logan International Airport 06:00 - ORD 08:06 3h 06m Direct
      • BOSBoston Logan International Airport 06:00
      • ORDChicago O'Hare International Airport 08:06
      • 3h 06m
      • Direct
      • JetBlue Airways (B6 311)Airbus A220 300
      • JetBlue Airways (B6 311)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • Airbus A220 300
      • 06:02 BOS
        08:05 ORD
        3Hrs, 03m Direct
      • BOSBoston Logan International Airport 06:02 - ORD 08:05 3h 03m Direct
      • BOSBoston Logan International Airport 06:02
      • ORDChicago O'Hare International Airport 08:05
      • 3h 03m
      • Direct
      • United Airlines (UA 1414)Boeing 737 700
      • United Airlines (UA 1414)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 700
      • 06:02 BOS
        08:05 ORD
        3Hrs, 03m Direct
      • BOSBoston Logan International Airport 06:02 - ORD 08:05 3h 03m Direct
      • BOSBoston Logan International Airport 06:02
      • ORDChicago O'Hare International Airport 08:05
      • 3h 03m
      • Direct
      • United Airlines (UA 1414)Boeing 737 800
      • United Airlines (UA 1414)
        • -
        • -
        • -
        • T
        • F
        • -
        • -
      • Boeing 737 800
      • 06:02 BOS
        08:05 ORD
        3Hrs, 03m Direct
      • BOSBoston Logan International Airport 06:02 - ORD 08:05 3h 03m Direct
      • BOSBoston Logan International Airport 06:02
      • ORDChicago O'Hare International Airport 08:05
      • 3h 03m
      • Direct
      • United Airlines (UA 1414)Boeing 737 Max 8 Passenger
      • United Airlines (UA 1414)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 Max 8 Passenger
      • 06:25 BOS
        08:15 MDW
        2Hrs, 50m Direct
      • BOSBoston Logan International Airport 06:25 - MDW 08:15 2h 50m Direct
      • BOSBoston Logan International Airport 06:25
      • MDWChicago Midway Airport 08:15
      • 2h 50m
      • Direct
      • Southwest Airlines (WN 3914)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 3914)
        • -
        • -
        • -
        • -
        • F
        • -
        • S
      • Boeing 737 Max 8 Passenger
      • 06:30 BOS
        08:36 ORD
        3Hrs, 06m Direct
      • BOSBoston Logan International Airport 06:30 - ORD 08:36 3h 06m Direct
      • BOSBoston Logan International Airport 06:30
      • ORDChicago O'Hare International Airport 08:36
      • 3h 06m
      • Direct
      • American Airlines (AA 1509)Boeing 737 800
      • American Airlines (AA 1509)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 800
      • 06:40 BOS
        08:25 MDW
        2Hrs, 45m Direct
      • BOSBoston Logan International Airport 06:40 - MDW 08:25 2h 45m Direct
      • BOSBoston Logan International Airport 06:40
      • MDWChicago Midway Airport 08:25
      • 2h 45m
      • Direct
      • Southwest Airlines (WN 787)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 787)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 06:45 BOS
        08:49 ORD
        3Hrs, 04m Direct
      • BOSBoston Logan International Airport 06:45 - ORD 08:49 3h 04m Direct
      • BOSBoston Logan International Airport 06:45
      • ORDChicago O'Hare International Airport 08:49
      • 3h 04m
      • Direct
      • American Airlines (AA 1509)Boeing 737 800
      • American Airlines (AA 1509)
        • -
        • -
        • -
        • -
        • F
        • -
        • S
      • Boeing 737 800
      • 06:45 BOS
        08:57 ORD
        3Hrs, 12m Direct
      • BOSBoston Logan International Airport 06:45 - ORD 08:57 3h 12m Direct
      • BOSBoston Logan International Airport 06:45
      • ORDChicago O'Hare International Airport 08:57
      • 3h 12m
      • Direct
      • American Airlines (AA 4711)Embraer Emb 175
      • American Airlines (AA 4711)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • Embraer Emb 175
      • 07:00 BOS
        08:45 MDW
        2Hrs, 45m Direct
      • BOSBoston Logan International Airport 07:00 - MDW 08:45 2h 45m Direct
      • BOSBoston Logan International Airport 07:00
      • MDWChicago Midway Airport 08:45
      • 2h 45m
      • Direct
      • Southwest Airlines (WN 787)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 787)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 08:45 BOS
        10:49 ORD
        3Hrs, 04m Direct
      • BOSBoston Logan International Airport 08:45 - ORD 10:49 3h 04m Direct
      • BOSBoston Logan International Airport 08:45
      • ORDChicago O'Hare International Airport 10:49
      • 3h 04m
      • Direct
      • American Airlines (AA 2351)Boeing 737 800
      • American Airlines (AA 2351)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • Boeing 737 800
      • 08:45 BOS
        10:52 ORD
        3Hrs, 07m Direct
      • BOSBoston Logan International Airport 08:45 - ORD 10:52 3h 07m Direct
      • BOSBoston Logan International Airport 08:45
      • ORDChicago O'Hare International Airport 10:52
      • 3h 07m
      • Direct
      • American Airlines (AA 2163)Boeing 737 800
      • American Airlines (AA 2163)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 800
      • 08:45 BOS
        10:49 ORD
        3Hrs, 04m Direct
      • BOSBoston Logan International Airport 08:45 - ORD 10:49 3h 04m Direct
      • BOSBoston Logan International Airport 08:45
      • ORDChicago O'Hare International Airport 10:49
      • 3h 04m
      • Direct
      • American Airlines (AA 1741)Boeing 737 800
      • American Airlines (AA 1741)
        • -
        • -
        • -
        • -
        • F
        • -
        • S
      • Boeing 737 800
      • 09:30 BOS
        11:28 ORD
        2Hrs, 58m Direct
      • BOSBoston Logan International Airport 09:30 - ORD 11:28 2h 58m Direct
      • BOSBoston Logan International Airport 09:30
      • ORDChicago O'Hare International Airport 11:28
      • 2h 58m
      • Direct
      • United Airlines (UA 378)Boeing 737 800
      • United Airlines (UA 378)
        • -
        • -
        • -
        • T
        • F
        • S
        • S
      • Boeing 737 800
      • 09:30 BOS
        11:26 ORD
        2Hrs, 56m Direct
      • BOSBoston Logan International Airport 09:30 - ORD 11:26 2h 56m Direct
      • BOSBoston Logan International Airport 09:30
      • ORDChicago O'Hare International Airport 11:26
      • 2h 56m
      • Direct
      • United Airlines (UA 378)Boeing 737 800
      • United Airlines (UA 378)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 800
      • 10:15 BOS
        12:18 ORD
        3Hrs, 03m Direct
      • BOSBoston Logan International Airport 10:15 - ORD 12:18 3h 03m Direct
      • BOSBoston Logan International Airport 10:15
      • ORDChicago O'Hare International Airport 12:18
      • 3h 03m
      • Direct
      • American Airlines (AA 1509)Boeing 737 800
      • American Airlines (AA 1509)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • Boeing 737 800
      • 10:25 BOS
        12:10 MDW
        2Hrs, 45m Direct
      • BOSBoston Logan International Airport 10:25 - MDW 12:10 2h 45m Direct
      • BOSBoston Logan International Airport 10:25
      • MDWChicago Midway Airport 12:10
      • 2h 45m
      • Direct
      • Southwest Airlines (WN 935)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 935)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 Max 8 Passenger
      • 10:45 BOS
        12:41 ORD
        2Hrs, 56m Direct
      • BOSBoston Logan International Airport 10:45 - ORD 12:41 2h 56m Direct
      • BOSBoston Logan International Airport 10:45
      • ORDChicago O'Hare International Airport 12:41
      • 2h 56m
      • Direct
      • United Airlines (UA 1631)Boeing 737 800
      • United Airlines (UA 1631)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 800
      • 10:50 BOS
        12:35 MDW
        2Hrs, 45m Direct
      • BOSBoston Logan International Airport 10:50 - MDW 12:35 2h 45m Direct
      • BOSBoston Logan International Airport 10:50
      • MDWChicago Midway Airport 12:35
      • 2h 45m
      • Direct
      • Southwest Airlines (WN 787)Boeing 737 800
      • Southwest Airlines (WN 787)
        • -
        • -
        • -
        • -
        • F
        • -
        • S
      • Boeing 737 800
      • 11:02 BOS
        13:00 ORD
        2Hrs, 58m Direct
      • BOSBoston Logan International Airport 11:02 - ORD 13:00 2h 58m Direct
      • BOSBoston Logan International Airport 11:02
      • ORDChicago O'Hare International Airport 13:00
      • 2h 58m
      • Direct
      • United Airlines (UA 267)Airbus
      • United Airlines (UA 267)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Airbus
      • 11:07 BOS
        13:05 ORD
        2Hrs, 58m Direct
      • BOSBoston Logan International Airport 11:07 - ORD 13:05 2h 58m Direct
      • BOSBoston Logan International Airport 11:07
      • ORDChicago O'Hare International Airport 13:05
      • 2h 58m
      • Direct
      • United Airlines (UA 267)Boeing 737 800
      • United Airlines (UA 267)
        • -
        • -
        • -
        • T
        • F
        • -
        • -
      • Boeing 737 800
      • 12:13 BOS
        14:22 ORD
        3Hrs, 09m Direct
      • BOSBoston Logan International Airport 12:13 - ORD 14:22 3h 09m Direct
      • BOSBoston Logan International Airport 12:13
      • ORDChicago O'Hare International Airport 14:22
      • 3h 09m
      • Direct
      • American Airlines (AA 4470)Embraer Emb 175
      • American Airlines (AA 4470)
        • -
        • -
        • -
        • T
        • F
        • -
        • S
      • Embraer Emb 175
      • 12:20 BOS
        14:19 ORD
        2Hrs, 59m Direct
      • BOSBoston Logan International Airport 12:20 - ORD 14:19 2h 59m Direct
      • BOSBoston Logan International Airport 12:20
      • ORDChicago O'Hare International Airport 14:19
      • 2h 59m
      • Direct
      • United Airlines (UA 1732)Boeing 737 700
      • United Airlines (UA 1732)
        • -
        • -
        • -
        • T
        • F
        • S
        • S
      • Boeing 737 700
      • 12:22 BOS
        14:31 ORD
        3Hrs, 09m Direct
      • BOSBoston Logan International Airport 12:22 - ORD 14:31 3h 09m Direct
      • BOSBoston Logan International Airport 12:22
      • ORDChicago O'Hare International Airport 14:31
      • 3h 09m
      • Direct
      • American Airlines (AA 4470)Embraer Emb 175
      • American Airlines (AA 4470)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Embraer Emb 175
      • 12:25 BOS
        14:21 ORD
        2Hrs, 56m Direct
      • BOSBoston Logan International Airport 12:25 - ORD 14:21 2h 56m Direct
      • BOSBoston Logan International Airport 12:25
      • ORDChicago O'Hare International Airport 14:21
      • 2h 56m
      • Direct
      • United Airlines (UA 1732)Boeing 737 Max 8 Passenger
      • United Airlines (UA 1732)
        • -
        • T
        • -
        • -
        • -
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 12:25 BOS
        14:21 ORD
        2Hrs, 56m Direct
      • BOSBoston Logan International Airport 12:25 - ORD 14:21 2h 56m Direct
      • BOSBoston Logan International Airport 12:25
      • ORDChicago O'Hare International Airport 14:21
      • 2h 56m
      • Direct
      • United Airlines (UA 1732)Airbus A321 Neo
      • United Airlines (UA 1732)
        • M
        • -
        • W
        • -
        • -
        • -
        • -
      • Airbus A321 Neo
      • 13:59 BOS
        15:53 ORD
        2Hrs, 54m Direct
      • BOSBoston Logan International Airport 13:59 - ORD 15:53 2h 54m Direct
      • BOSBoston Logan International Airport 13:59
      • ORDChicago O'Hare International Airport 15:53
      • 2h 54m
      • Direct
      • JetBlue Airways (B6 611)Embraer Emb E90
      • JetBlue Airways (B6 611)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • Embraer Emb E90
      • 14:26 BOS
        16:29 ORD
        3Hrs, 03m Direct
      • BOSBoston Logan International Airport 14:26 - ORD 16:29 3h 03m Direct
      • BOSBoston Logan International Airport 14:26
      • ORDChicago O'Hare International Airport 16:29
      • 3h 03m
      • Direct
      • American Airlines (AA 514)Boeing 737 800
      • American Airlines (AA 514)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 800
      • 14:55 BOS
        16:40 MDW
        2Hrs, 45m Direct
      • BOSBoston Logan International Airport 14:55 - MDW 16:40 2h 45m Direct
      • BOSBoston Logan International Airport 14:55
      • MDWChicago Midway Airport 16:40
      • 2h 45m
      • Direct
      • Southwest Airlines (WN 3249)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 3249)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 15:15 BOS
        17:00 MDW
        2Hrs, 45m Direct
      • BOSBoston Logan International Airport 15:15 - MDW 17:00 2h 45m Direct
      • BOSBoston Logan International Airport 15:15
      • MDWChicago Midway Airport 17:00
      • 2h 45m
      • Direct
      • Southwest Airlines (WN 3617)Boeing 737 700
      • Southwest Airlines (WN 3617)
        • -
        • -
        • -
        • -
        • F
        • -
        • S
      • Boeing 737 700
      • 15:50 BOS
        17:50 ORD
        3Hrs, 00m Direct
      • BOSBoston Logan International Airport 15:50 - ORD 17:50 3h Direct
      • BOSBoston Logan International Airport 15:50
      • ORDChicago O'Hare International Airport 17:50
      • 3h
      • Direct
      • American Airlines (AA 514)Airbus
      • American Airlines (AA 514)
        • -
        • -
        • -
        • T
        • -
        • S
        • S
      • Airbus
      • 16:00 BOS
        18:06 ORD
        3Hrs, 06m Direct
      • BOSBoston Logan International Airport 16:00 - ORD 18:06 3h 06m Direct
      • BOSBoston Logan International Airport 16:00
      • ORDChicago O'Hare International Airport 18:06
      • 3h 06m
      • Direct
      • American Airlines (AA 4413)Embraer Emb 175
      • American Airlines (AA 4413)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • Embraer Emb 175
      • 16:10 BOS
        18:10 ORD
        3Hrs, 00m Direct
      • BOSBoston Logan International Airport 16:10 - ORD 18:10 3h Direct
      • BOSBoston Logan International Airport 16:10
      • ORDChicago O'Hare International Airport 18:10
      • 3h
      • Direct
      • American Airlines (AA 514)Airbus
      • American Airlines (AA 514)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • Airbus
      • 16:15 BOS
        18:00 MDW
        2Hrs, 45m Direct
      • BOSBoston Logan International Airport 16:15 - MDW 18:00 2h 45m Direct
      • BOSBoston Logan International Airport 16:15
      • MDWChicago Midway Airport 18:00
      • 2h 45m
      • Direct
      • Southwest Airlines (WN 3586)Boeing 737 700
      • Southwest Airlines (WN 3586)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 700
      • 16:23 BOS
        18:19 ORD
        2Hrs, 56m Direct
      • BOSBoston Logan International Airport 16:23 - ORD 18:19 2h 56m Direct
      • BOSBoston Logan International Airport 16:23
      • ORDChicago O'Hare International Airport 18:19
      • 2h 56m
      • Direct
      • United Airlines (UA 2040)Boeing 737 Max 8 Passenger
      • United Airlines (UA 2040)
        • M
        • T
        • -
        • -
        • -
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 16:23 BOS
        18:19 ORD
        2Hrs, 56m Direct
      • BOSBoston Logan International Airport 16:23 - ORD 18:19 2h 56m Direct
      • BOSBoston Logan International Airport 16:23
      • ORDChicago O'Hare International Airport 18:19
      • 2h 56m
      • Direct
      • United Airlines (UA 2040)Boeing 737 700
      • United Airlines (UA 2040)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 700
      • 16:25 BOS
        18:25 ORD
        3Hrs, 00m Direct
      • BOSBoston Logan International Airport 16:25 - ORD 18:25 3h Direct
      • BOSBoston Logan International Airport 16:25
      • ORDChicago O'Hare International Airport 18:25
      • 3h
      • Direct
      • United Airlines (UA 2040)Boeing 737 900
      • United Airlines (UA 2040)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • Boeing 737 900
      • 16:25 BOS
        18:25 ORD
        3Hrs, 00m Direct
      • BOSBoston Logan International Airport 16:25 - ORD 18:25 3h Direct
      • BOSBoston Logan International Airport 16:25
      • ORDChicago O'Hare International Airport 18:25
      • 3h
      • Direct
      • United Airlines (UA 2040)Airbus
      • United Airlines (UA 2040)
        • -
        • -
        • -
        • -
        • F
        • S
        • S
      • Airbus
      • 17:42 BOS
        19:45 ORD
        3Hrs, 03m Direct
      • BOSBoston Logan International Airport 17:42 - ORD 19:45 3h 03m Direct
      • BOSBoston Logan International Airport 17:42
      • ORDChicago O'Hare International Airport 19:45
      • 3h 03m
      • Direct
      • American Airlines (AA 2877)Boeing 737 800
      • American Airlines (AA 2877)
        • -
        • -
        • -
        • T
        • F
        • S
        • S
      • Boeing 737 800
      • 17:46 BOS
        19:50 ORD
        3Hrs, 04m Direct
      • BOSBoston Logan International Airport 17:46 - ORD 19:50 3h 04m Direct
      • BOSBoston Logan International Airport 17:46
      • ORDChicago O'Hare International Airport 19:50
      • 3h 04m
      • Direct
      • American Airlines (AA 2151)Boeing 737 800
      • American Airlines (AA 2151)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 800
      • 18:00 BOS
        19:45 MDW
        2Hrs, 45m Direct
      • BOSBoston Logan International Airport 18:00 - MDW 19:45 2h 45m Direct
      • BOSBoston Logan International Airport 18:00
      • MDWChicago Midway Airport 19:45
      • 2h 45m
      • Direct
      • Southwest Airlines (WN 1549)Boeing 737 800
      • Southwest Airlines (WN 1549)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 800
      • 18:25 BOS
        20:25 ORD
        3Hrs, 00m Direct
      • BOSBoston Logan International Airport 18:25 - ORD 20:25 3h Direct
      • BOSBoston Logan International Airport 18:25
      • ORDChicago O'Hare International Airport 20:25
      • 3h
      • Direct
      • United Airlines (UA 1015)Airbus A321 Neo
      • United Airlines (UA 1015)
        • -
        • -
        • -
        • -
        • -
        • S
        • S
      • Airbus A321 Neo
      • 18:25 BOS
        20:25 ORD
        3Hrs, 00m Direct
      • BOSBoston Logan International Airport 18:25 - ORD 20:25 3h Direct
      • BOSBoston Logan International Airport 18:25
      • ORDChicago O'Hare International Airport 20:25
      • 3h
      • Direct
      • United Airlines (UA 1015)Boeing 737 800
      • United Airlines (UA 1015)
        • -
        • -
        • -
        • T
        • F
        • -
        • -
      • Boeing 737 800
      • 18:28 BOS
        20:24 ORD
        2Hrs, 56m Direct
      • BOSBoston Logan International Airport 18:28 - ORD 20:24 2h 56m Direct
      • BOSBoston Logan International Airport 18:28
      • ORDChicago O'Hare International Airport 20:24
      • 2h 56m
      • Direct
      • United Airlines (UA 1134)Airbus A321 Neo
      • United Airlines (UA 1134)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • Airbus A321 Neo
      • 19:00 BOS
        23:15 MDW
        5Hrs, 15m 1 Stop (STL)
      • BOSBoston Logan International Airport 19:00 - MDW 23:15 5h 15m 1 Stop (STL) Saint Louis
      • BOSBoston Logan International Airport 19:00
        STLSt Louis Lambert Intl Airport 22:05
      • STLSt Louis Lambert Intl Airport 21:10
        MDWChicago Midway Airport 23:15
      • 5h 15m (55m)
      • 1 Stop STL · Saint Louis 55m
      • Southwest Airlines (WN 4217)Boeing 737 800
        Southwest Airlines (WN 652)Boeing 737 800
      • Southwest Airlines (WN 4217)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • 19:05 BOS
        23:55 MDW
        5Hrs, 50m 1 Stop (STL)
      • BOSBoston Logan International Airport 19:05 - MDW 23:55 5h 50m 1 Stop (STL) Saint Louis
      • BOSBoston Logan International Airport 19:05
        STLSt Louis Lambert Intl Airport 22:45
      • STLSt Louis Lambert Intl Airport 21:15
        MDWChicago Midway Airport 23:55
      • 5h 50m (1h 30m)
      • 1 Stop STL · Saint Louis 1h 30m
      • Southwest Airlines (WN 4217)Boeing 737 800
        Southwest Airlines (WN 652)Boeing 737 700
      • Southwest Airlines (WN 4217)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 19:37 BOS
        23:25 ORD
        4Hrs, 48m 1 Stop (IAD)
      • BOSBoston Logan International Airport 19:37 - ORD 23:25 4h 48m 1 Stop (IAD) Washington
      • BOSBoston Logan International Airport 19:37
        IADWashington Dulles International Airport 22:20
      • IADWashington Dulles International Airport 21:25
        ORDChicago O'Hare International Airport 23:25
      • 4h 48m (55m)
      • 1 Stop IAD · Washington 55m
      • United Airlines (UA 3547)Embraer 175
        United Airlines (UA 1738)Boeing 757 200 Series
      • United Airlines (UA 3547)
        • -
        • -
        • -
        • -
        • -
        • S
        • S
      • 19:38 BOS
        23:20 ORD
        4Hrs, 42m 1 Stop (IAD)
      • BOSBoston Logan International Airport 19:38 - ORD 23:20 4h 42m 1 Stop (IAD) Washington
      • BOSBoston Logan International Airport 19:38
        IADWashington Dulles International Airport 22:16
      • IADWashington Dulles International Airport 21:25
        ORDChicago O'Hare International Airport 23:20
      • 4h 42m (51m)
      • 1 Stop IAD · Washington 51m
      • United Airlines (UA 2136)Boeing 737 Max 8 Passenger
        United Airlines (UA 1738)Boeing 737 800
      • United Airlines (UA 2136)
        • M
        • T
        • -
        • -
        • -
        • -
        • -
      • 19:38 BOS
        23:20 ORD
        4Hrs, 42m 1 Stop (IAD)
      • BOSBoston Logan International Airport 19:38 - ORD 23:20 4h 42m 1 Stop (IAD) Washington
      • BOSBoston Logan International Airport 19:38
        IADWashington Dulles International Airport 22:16
      • IADWashington Dulles International Airport 21:25
        ORDChicago O'Hare International Airport 23:20
      • 4h 42m (51m)
      • 1 Stop IAD · Washington 51m
      • United Airlines (UA 2136)Boeing 737 900
        United Airlines (UA 1738)Boeing 757 200 Series
      • United Airlines (UA 2136)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • 19:42 BOS
        23:25 ORD
        4Hrs, 43m 1 Stop (IAD)
      • BOSBoston Logan International Airport 19:42 - ORD 23:25 4h 43m 1 Stop (IAD) Washington
      • BOSBoston Logan International Airport 19:42
        IADWashington Dulles International Airport 22:20
      • IADWashington Dulles International Airport 21:25
        ORDChicago O'Hare International Airport 23:25
      • 4h 43m (55m)
      • 1 Stop IAD · Washington 55m
      • United Airlines (UA 2136)Airbus
        United Airlines (UA 1738)Boeing 757 200 Series
      • United Airlines (UA 2136)
        • -
        • -
        • -
        • T
        • F
        • -
        • -
      • 19:45 BOS
        23:55 MDW
        5Hrs, 10m 1 Stop (BNA)
      • BOSBoston Logan International Airport 19:45 - MDW 23:55 5h 10m 1 Stop (BNA)
      • BOSBoston Logan International Airport 19:45
        BNANashville Airport 22:25
      • BNANashville Airport 21:40
        MDWChicago Midway Airport 23:55
      • 5h 10m (45m)
      • 1 Stop BNA · 45m
      • Southwest Airlines (WN 4285)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1647)Boeing 737 700
      • Southwest Airlines (WN 4285)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • 19:55 BOS
        00:25 MDW
        5Hrs, 30m 1 Stop (BNA)
      • BOSBoston Logan International Airport 19:55 - MDW 00:25 5h 30m 1 Stop (BNA)
      • BOSBoston Logan International Airport 19:55
        BNANashville Airport 22:50
      • BNANashville Airport 21:50
        MDWChicago Midway Airport 00:25
      • 5h 30m (1h)
      • 1 Stop BNA · 1h
      • Southwest Airlines (WN 4285)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1647)Boeing 737 800
      • Southwest Airlines (WN 4285)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 20:05 BOS
        00:20 MDW
        5Hrs, 15m 1 Stop (BNA)
      • BOSBoston Logan International Airport 20:05 - MDW 00:20 5h 15m 1 Stop (BNA)
      • BOSBoston Logan International Airport 20:05
        BNANashville Airport 22:45
      • BNANashville Airport 22:00
        MDWChicago Midway Airport 00:20
      • 5h 15m (45m)
      • 1 Stop BNA · 45m
      • Southwest Airlines (WN 2141)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 2804)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 2141)
        • -
        • -
        • -
        • -
        • F
        • -
        • S
      • 05:00 BOS
        10:20 MDW
        6Hrs, 20m 1 Stop (BNA)
      • BOSBoston Logan International Airport 05:00 - MDW 10:20 6h 20m 1 Stop (BNA)
      • BOSBoston Logan International Airport 05:00
        BNANashville Airport 08:45
      • BNANashville Airport 06:55
        MDWChicago Midway Airport 10:20
      • 6h 20m (1h 50m)
      • 1 Stop BNA · 1h 50m
      • Southwest Airlines (WN 100)Boeing 737 700
        Southwest Airlines (WN 6342)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 100)
        • -
        • -
        • -
        • -
        • F
        • -
        • S
      • 05:15 BOS
        11:01 ORD
        6Hrs, 46m 1 Stop (CLT)
      • BOSBoston Logan International Airport 05:15 - ORD 11:01 6h 46m 1 Stop (CLT) Charlotte
      • BOSBoston Logan International Airport 05:15
        CLTCharlotte Airport 09:40
      • CLTCharlotte Airport 07:49
        ORDChicago O'Hare International Airport 11:01
      • 6h 46m (1h 51m)
      • 1 Stop CLT · Charlotte 1h 51m
      • American Airlines (AA 624)Boeing 737 800
        American Airlines (AA 1668)Boeing 737 Max 8 Passenger
      • American Airlines (AA 624)
        • -
        • -
        • -
        • T
        • F
        • S
        • S
      • 05:17 BOS
        10:31 ORD
        6Hrs, 14m 1 Stop (CLT)
      • BOSBoston Logan International Airport 05:17 - ORD 10:31 6h 14m 1 Stop (CLT) Charlotte
      • BOSBoston Logan International Airport 05:17
        CLTCharlotte Airport 09:13
      • CLTCharlotte Airport 07:54
        ORDChicago O'Hare International Airport 10:31
      • 6h 14m (1h 19m)
      • 1 Stop CLT · Charlotte 1h 19m
      • American Airlines (AA 624)Boeing 737 800
        American Airlines (AA 1668)Boeing 737 Max 8 Passenger
      • American Airlines (AA 624)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • 05:25 BOS
        10:20 MDW
        5Hrs, 55m 1 Stop (BWI)
      • BOSBoston Logan International Airport 05:25 - MDW 10:20 5h 55m 1 Stop (BWI) Baltimore
      • BOSBoston Logan International Airport 05:25
        BWIBaltimore Washington International Airport 09:10
      • BWIBaltimore Washington International Airport 07:05
        MDWChicago Midway Airport 10:20
      • 5h 55m (2h 05m)
      • 1 Stop BWI · Baltimore 2h 05m
      • Southwest Airlines (WN 369)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 6315)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 369)
        • -
        • -
        • -
        • -
        • F
        • -
        • S
      • 05:40 BOS
        10:40 MDW
        6Hrs, 00m 1 Stop (BWI)
      • BOSBoston Logan International Airport 05:40 - MDW 10:40 6h 1 Stop (BWI) Baltimore
      • BOSBoston Logan International Airport 05:40
        BWIBaltimore Washington International Airport 09:35
      • BWIBaltimore Washington International Airport 07:20
        MDWChicago Midway Airport 10:40
      • 6h (2h 15m)
      • 1 Stop BWI · Baltimore 2h 15m
      • Southwest Airlines (WN 369)Boeing 737 800
        Southwest Airlines (WN 5265)Boeing 737 700
      • Southwest Airlines (WN 369)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • 05:40 BOS
        11:00 ORD
        6Hrs, 20m 1 Stop (PHL)
      • BOSBoston Logan International Airport 05:40 - ORD 11:00 6h 20m 1 Stop (PHL) Philadelphia
      • BOSBoston Logan International Airport 05:40
        PHLPhiladelphia International Airport 09:30
      • PHLPhiladelphia International Airport 07:20
        ORDChicago O'Hare International Airport 11:00
      • 6h 20m (2h 10m)
      • 1 Stop PHL · Philadelphia 2h 10m
      • American Airlines (AA 1875)Boeing 737 800
        American Airlines (AA 2095)Boeing 737 800
      • American Airlines (AA 1875)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • 05:45 BOS
        09:34 ORD
        4Hrs, 49m 1 Stop (IAD)
      • BOSBoston Logan International Airport 05:45 - ORD 09:34 4h 49m 1 Stop (IAD) Washington
      • BOSBoston Logan International Airport 05:45
        IADWashington Dulles International Airport 08:20
      • IADWashington Dulles International Airport 07:29
        ORDChicago O'Hare International Airport 09:34
      • 4h 49m (51m)
      • 1 Stop IAD · Washington 51m
      • United Airlines (UA 1734)Boeing 737 800
        United Airlines (UA 599)Boeing 737 900
      • United Airlines (UA 1734)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • 05:45 BOS
        09:55 ORD
        5Hrs, 10m 1 Stop (IAD)
      • BOSBoston Logan International Airport 05:45 - ORD 09:55 5h 10m 1 Stop (IAD) Washington
      • BOSBoston Logan International Airport 05:45
        IADWashington Dulles International Airport 08:35
      • IADWashington Dulles International Airport 07:31
        ORDChicago O'Hare International Airport 09:55
      • 5h 10m (1h 04m)
      • 1 Stop IAD · Washington 1h 04m
      • United Airlines (UA 1734)Boeing 737 800
        United Airlines (UA 1710)Airbus
      • United Airlines (UA 1734)
        • -
        • -
        • -
        • -
        • F
        • S
        • S
      • 05:45 BOS
        09:55 ORD
        5Hrs, 10m 1 Stop (IAD)
      • BOSBoston Logan International Airport 05:45 - ORD 09:55 5h 10m 1 Stop (IAD) Washington
      • BOSBoston Logan International Airport 05:45
        IADWashington Dulles International Airport 08:35
      • IADWashington Dulles International Airport 07:31
        ORDChicago O'Hare International Airport 09:55
      • 5h 10m (1h 04m)
      • 1 Stop IAD · Washington 1h 04m
      • United Airlines (UA 1734)Boeing 737 Max 9 Passenger
        United Airlines (UA 1710)Boeing 757 200 Series
      • United Airlines (UA 1734)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • 05:50 BOS
        10:53 ORD
        6Hrs, 03m 1 Stop (PHL)
      • BOSBoston Logan International Airport 05:50 - ORD 10:53 6h 03m 1 Stop (PHL) Philadelphia
      • BOSBoston Logan International Airport 05:50
        PHLPhiladelphia International Airport 09:24
      • PHLPhiladelphia International Airport 07:27
        ORDChicago O'Hare International Airport 10:53
      • 6h 03m (1h 57m)
      • 1 Stop PHL · Philadelphia 1h 57m
      • American Airlines (AA 1114)Boeing 737 800
        American Airlines (AA 1606)Airbus
      • American Airlines (AA 1114)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • 05:50 BOS
        11:03 ORD
        6Hrs, 13m 1 Stop (DCA)
      • BOSBoston Logan International Airport 05:50 - ORD 11:03 6h 13m 1 Stop (DCA) Washington
      • BOSBoston Logan International Airport 05:50
        DCAWashington Ronald Reagan National Airport 09:43
      • DCAWashington Ronald Reagan National Airport 07:43
        ORDChicago O'Hare International Airport 11:03
      • 6h 13m (2h)
      • 1 Stop DCA · Washington 2h
      • American Airlines (AA 4446)Embraer Emb 175
        American Airlines (AA 1200)Airbus
      • American Airlines (AA 4446)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • 05:54 BOS
        10:41 ORD
        5Hrs, 47m 1 Stop (PHL)
      • BOSBoston Logan International Airport 05:54 - ORD 10:41 5h 47m 1 Stop (PHL) Philadelphia
      • BOSBoston Logan International Airport 05:54
        PHLPhiladelphia International Airport 09:14
      • PHLPhiladelphia International Airport 07:31
        ORDChicago O'Hare International Airport 10:41
      • 5h 47m (1h 43m)
      • 1 Stop PHL · Philadelphia 1h 43m
      • American Airlines (AA 1114)Boeing 737 800
        American Airlines (AA 1606)Airbus
      • American Airlines (AA 1114)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 05:54 BOS
        10:53 ORD
        5Hrs, 59m 1 Stop (PHL)
      • BOSBoston Logan International Airport 05:54 - ORD 10:53 5h 59m 1 Stop (PHL) Philadelphia
      • BOSBoston Logan International Airport 05:54
        PHLPhiladelphia International Airport 09:24
      • PHLPhiladelphia International Airport 07:31
        ORDChicago O'Hare International Airport 10:53
      • 5h 59m (1h 53m)
      • 1 Stop PHL · Philadelphia 1h 53m
      • American Airlines (AA 1114)Boeing 737 800
        American Airlines (AA 1606)Airbus
      • American Airlines (AA 1114)
        • -
        • -
        • -
        • -
        • F
        • -
        • S
      • 05:56 BOS
        11:02 ORD
        6Hrs, 06m 1 Stop (DCA)
      • BOSBoston Logan International Airport 05:56 - ORD 11:02 6h 06m 1 Stop (DCA) Washington
      • BOSBoston Logan International Airport 05:56
        DCAWashington Ronald Reagan National Airport 09:44
      • DCAWashington Ronald Reagan National Airport 07:44
        ORDChicago O'Hare International Airport 11:02
      • 6h 06m (2h)
      • 1 Stop DCA · Washington 2h
      • American Airlines (AA 2159)Airbus
        American Airlines (AA 1200)Airbus
      • American Airlines (AA 2159)
        • -
        • -
        • -
        • T
        • F
        • -
        • -
      • 05:56 BOS
        10:55 ORD
        5Hrs, 59m 1 Stop (DCA)
      • BOSBoston Logan International Airport 05:56 - ORD 10:55 5h 59m 1 Stop (DCA) Washington
      • BOSBoston Logan International Airport 05:56
        DCAWashington Ronald Reagan National Airport 09:29
      • DCAWashington Ronald Reagan National Airport 07:44
        ORDChicago O'Hare International Airport 10:55
      • 5h 59m (1h 45m)
      • 1 Stop DCA · Washington 1h 45m
      • American Airlines (AA 2159)Airbus
        American Airlines (AA 4391)Embraer Emb 175
      • American Airlines (AA 2159)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 06:00 BOS
        11:38 ORD
        6Hrs, 38m 1 Stop (EWR)
      • BOSBoston Logan International Airport 06:00 - ORD 11:38 6h 38m 1 Stop (EWR) New York City
      • BOSBoston Logan International Airport 06:00
        EWRNewark Liberty International Airport 10:00
      • EWRNewark Liberty International Airport 07:28
        ORDChicago O'Hare International Airport 11:38
      • 6h 38m (2h 32m)
      • 1 Stop EWR · New York City 2h 32m
      • United Airlines (UA 1833)Boeing 757 200 Series
        United Airlines (UA 1525)Boeing 737 900
      • United Airlines (UA 1833)
        • -
        • -
        • -
        • -
        • F
        • -
        • S
      • 06:00 BOS
        11:16 ORD
        6Hrs, 16m 1 Stop (LGA)
      • BOSBoston Logan International Airport 06:00 - ORD 11:16 6h 16m 1 Stop (LGA) New York City
      • BOSBoston Logan International Airport 06:00
        LGANew York La Guardia Airport 09:29
      • LGANew York La Guardia Airport 07:27
        ORDChicago O'Hare International Airport 11:16
      • 6h 16m (2h 02m)
      • 1 Stop LGA · New York City 2h 02m
      • American Airlines (AA 4439)Embraer Emb 175
        American Airlines (AA 2084)Airbus
      • American Airlines (AA 4439)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • 06:00 BOS
        11:44 ORD
        6Hrs, 44m 1 Stop (LGA)
      • BOSBoston Logan International Airport 06:00 - ORD 11:44 6h 44m 1 Stop (LGA) New York City
      • BOSBoston Logan International Airport 06:00
        LGANew York La Guardia Airport 09:59
      • LGANew York La Guardia Airport 07:30
        ORDChicago O'Hare International Airport 11:44
      • 6h 44m (2h 29m)
      • 1 Stop LGA · New York City 2h 29m
      • American Airlines (AA 4572)Embraer Emb 175
        American Airlines (AA 1152)Boeing 737 800
      • American Airlines (AA 4572)
        • -
        • -
        • -
        • T
        • F
        • -
        • S
      • 06:00 BOS
        10:53 ORD
        5Hrs, 53m 1 Stop (EWR)
      • BOSBoston Logan International Airport 06:00 - ORD 10:53 5h 53m 1 Stop (EWR) New York City
      • BOSBoston Logan International Airport 06:00
        EWRNewark Liberty International Airport 09:00
      • EWRNewark Liberty International Airport 07:29
        ORDChicago O'Hare International Airport 10:53
      • 5h 53m (1h 31m)
      • 1 Stop EWR · New York City 1h 31m
      • United Airlines (UA 1833)Boeing 757 200 Series
        United Airlines (UA 2290)Boeing 737 900
      • United Airlines (UA 1833)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • 06:00 BOS
        11:38 ORD
        6Hrs, 38m 1 Stop (EWR)
      • BOSBoston Logan International Airport 06:00 - ORD 11:38 6h 38m 1 Stop (EWR) New York City
      • BOSBoston Logan International Airport 06:00
        EWRNewark Liberty International Airport 10:00
      • EWRNewark Liberty International Airport 07:28
        ORDChicago O'Hare International Airport 11:38
      • 6h 38m (2h 32m)
      • 1 Stop EWR · New York City 2h 32m
      • United Airlines (UA 1833)Boeing 757 200 Series
        United Airlines (UA 1525)Boeing 737 Max 8 Passenger
      • United Airlines (UA 1833)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 06:00 BOS
        10:43 ORD
        5Hrs, 43m 1 Stop (LGA)
      • BOSBoston Logan International Airport 06:00 - ORD 10:43 5h 43m 1 Stop (LGA) New York City
      • BOSBoston Logan International Airport 06:00
        LGANew York La Guardia Airport 09:01
      • LGANew York La Guardia Airport 07:30
        ORDChicago O'Hare International Airport 10:43
      • 5h 43m (1h 31m)
      • 1 Stop LGA · New York City 1h 31m
      • American Airlines (AA 4572)Embraer Emb 175
        American Airlines (AA 2404)Airbus
      • American Airlines (AA 4572)
        • -
        • -
        • -
        • T
        • F
        • -
        • S
      • 06:10 BOS
        11:38 ORD
        6Hrs, 28m 1 Stop (EWR)
      • BOSBoston Logan International Airport 06:10 - ORD 11:38 6h 28m 1 Stop (EWR) New York City
      • BOSBoston Logan International Airport 06:10
        EWRNewark Liberty International Airport 10:00
      • EWRNewark Liberty International Airport 07:38
        ORDChicago O'Hare International Airport 11:38
      • 6h 28m (2h 22m)
      • 1 Stop EWR · New York City 2h 22m
      • United Airlines (UA 1833)Boeing 757 200 Series
        United Airlines (UA 1525)Boeing 737 Max 9 Passenger
      • United Airlines (UA 1833)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • 06:25 BOS
        11:37 ORD
        6Hrs, 12m 1 Stop (STL)
      • BOSBoston Logan International Airport 06:25 - ORD 11:37 6h 12m 1 Stop (STL) Saint Louis
      • BOSBoston Logan International Airport 06:25
        STLSt Louis Lambert Intl Airport 10:16
      • STLSt Louis Lambert Intl Airport 08:42
        ORDChicago O'Hare International Airport 11:37
      • 6h 12m (1h 34m)
      • 1 Stop STL · Saint Louis 1h 34m
      • American Airlines (AA 4500)Embraer Emb 175
        American Airlines (AA 2526)Airbus
      • American Airlines (AA 4500)
        • -
        • -
        • -
        • T
        • F
        • -
        • S
      • 06:35 BOS
        11:01 ORD
        5Hrs, 26m 1 Stop (CLT)
      • BOSBoston Logan International Airport 06:35 - ORD 11:01 5h 26m 1 Stop (CLT) Charlotte
      • BOSBoston Logan International Airport 06:35
        CLTCharlotte Airport 09:40
      • CLTCharlotte Airport 09:10
        ORDChicago O'Hare International Airport 11:01
      • 5h 26m (30m)
      • 1 Stop CLT · Charlotte 30m
      • American Airlines (AA 1793)Airbus
        American Airlines (AA 1668)Boeing 737 Max 8 Passenger
      • American Airlines (AA 1793)
        • -
        • -
        • -
        • T
        • F
        • -
        • S
      • 06:35 BOS
        12:12 ORD
        6Hrs, 37m 1 Stop (CLT)
      • BOSBoston Logan International Airport 06:35 - ORD 12:12 6h 37m 1 Stop (CLT) Charlotte
      • BOSBoston Logan International Airport 06:35
        CLTCharlotte Airport 11:01
      • CLTCharlotte Airport 09:10
        ORDChicago O'Hare International Airport 12:12
      • 6h 37m (1h 51m)
      • 1 Stop CLT · Charlotte 1h 51m
      • American Airlines (AA 1793)Airbus
        American Airlines (AA 2279)Boeing 737 800
      • American Airlines (AA 1793)
        • -
        • -
        • -
        • T
        • F
        • -
        • S
      • 06:40 BOS
        12:07 ORD
        6Hrs, 27m 1 Stop (CLT)
      • BOSBoston Logan International Airport 06:40 - ORD 12:07 6h 27m 1 Stop (CLT) Charlotte
      • BOSBoston Logan International Airport 06:40
        CLTCharlotte Airport 10:59
      • CLTCharlotte Airport 09:15
        ORDChicago O'Hare International Airport 12:07
      • 6h 27m (1h 44m)
      • 1 Stop CLT · Charlotte 1h 44m
      • American Airlines (AA 1793)Airbus
        American Airlines (AA 2279)Boeing 737 800
      • American Airlines (AA 1793)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 06:40 BOS
        12:20 ORD
        6Hrs, 40m 1 Stop (PHL)
      • BOSBoston Logan International Airport 06:40 - ORD 12:20 6h 40m 1 Stop (PHL) Philadelphia
      • BOSBoston Logan International Airport 06:40
        PHLPhiladelphia International Airport 10:45
      • PHLPhiladelphia International Airport 08:19
        ORDChicago O'Hare International Airport 12:20
      • 6h 40m (2h 26m)
      • 1 Stop PHL · Philadelphia 2h 26m
      • American Airlines (AA 1114)Airbus A321 Neo
        American Airlines (AA 1920)Boeing 737 800
      • American Airlines (AA 1114)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • 06:40 BOS
        11:00 ORD
        5Hrs, 20m 1 Stop (PHL)
      • BOSBoston Logan International Airport 06:40 - ORD 11:00 5h 20m 1 Stop (PHL) Philadelphia
      • BOSBoston Logan International Airport 06:40
        PHLPhiladelphia International Airport 09:30
      • PHLPhiladelphia International Airport 08:19
        ORDChicago O'Hare International Airport 11:00
      • 5h 20m (1h 11m)
      • 1 Stop PHL · Philadelphia 1h 11m
      • American Airlines (AA 1114)Airbus A321 Neo
        American Airlines (AA 2095)Boeing 737 800
      • American Airlines (AA 1114)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • 06:56 BOS
        11:45 ORD
        5Hrs, 49m 1 Stop (IND)
      • BOSBoston Logan International Airport 06:56 - ORD 11:45 5h 49m 1 Stop (IND) Indianapolis
      • BOSBoston Logan International Airport 06:56
        INDIndianapolis Airport 11:30
      • INDIndianapolis Airport 09:43
        ORDChicago O'Hare International Airport 11:45
      • 5h 49m (1h 47m)
      • 1 Stop IND · Indianapolis 1h 47m
      • American Airlines (AA 4725)Embraer Emb 175
        American Airlines (AA 3899)Embraer 170
      • American Airlines (AA 4725)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • 06:57 BOS
        11:08 ORD
        5Hrs, 11m 1 Stop (IND)
      • BOSBoston Logan International Airport 06:57 - ORD 11:08 5h 11m 1 Stop (IND) Indianapolis
      • BOSBoston Logan International Airport 06:57
        INDIndianapolis Airport 10:55
      • INDIndianapolis Airport 09:44
        ORDChicago O'Hare International Airport 11:08
      • 5h 11m (1h 11m)
      • 1 Stop IND · Indianapolis 1h 11m
      • American Airlines (AA 4725)Embraer Emb 175
        American Airlines (AA 3713)Embraer 170
      • American Airlines (AA 4725)
        • -
        • -
        • -
        • T
        • F
        • -
        • S
      • 07:00 BOS
        11:03 ORD
        5Hrs, 03m 1 Stop (DCA)
      • BOSBoston Logan International Airport 07:00 - ORD 11:03 5h 03m 1 Stop (DCA) Washington
      • BOSBoston Logan International Airport 07:00
        DCAWashington Ronald Reagan National Airport 09:43
      • DCAWashington Ronald Reagan National Airport 08:54
        ORDChicago O'Hare International Airport 11:03
      • 5h 03m (49m)
      • 1 Stop DCA · Washington 49m
      • American Airlines (AA 3106)Airbus
        American Airlines (AA 1200)Airbus
      • American Airlines (AA 3106)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • 07:00 BOS
        11:50 ORD
        5Hrs, 50m 1 Stop (CMH)
      • BOSBoston Logan International Airport 07:00 - ORD 11:50 5h 50m 1 Stop (CMH) Columbus
      • BOSBoston Logan International Airport 07:00
        CMHColumbus Port Columbus Intl Airport 11:18
      • CMHColumbus Port Columbus Intl Airport 09:24
        ORDChicago O'Hare International Airport 11:50
      • 5h 50m (1h 54m)
      • 1 Stop CMH · Columbus 1h 54m
      • American Airlines (AA 4389)Embraer Emb 175
        American Airlines (AA 3842)Embraer 170
      • American Airlines (AA 4389)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • 07:00 BOS
        12:07 ORD
        6Hrs, 07m 1 Stop (CMH)
      • BOSBoston Logan International Airport 07:00 - ORD 12:07 6h 07m 1 Stop (CMH) Columbus
      • BOSBoston Logan International Airport 07:00
        CMHColumbus Port Columbus Intl Airport 11:36
      • CMHColumbus Port Columbus Intl Airport 09:30
        ORDChicago O'Hare International Airport 12:07
      • 6h 07m (2h 06m)
      • 1 Stop CMH · Columbus 2h 06m
      • American Airlines (AA 4389)Embraer Emb 175
        American Airlines (AA 6121)Crj Canadair Regional
      • American Airlines (AA 4389)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 07:00 BOS
        12:38 ORD
        6Hrs, 38m 1 Stop (CMH)
      • BOSBoston Logan International Airport 07:00 - ORD 12:38 6h 38m 1 Stop (CMH) Columbus
      • BOSBoston Logan International Airport 07:00
        CMHColumbus Port Columbus Intl Airport 12:11
      • CMHColumbus Port Columbus Intl Airport 09:30
        ORDChicago O'Hare International Airport 12:38
      • 6h 38m (2h 41m)
      • 1 Stop CMH · Columbus 2h 41m
      • American Airlines (AA 4750)Embraer Emb 175
        American Airlines (AA 3955)Embraer 170
      • American Airlines (AA 4750)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • 07:00 BOS
        12:38 ORD
        6Hrs, 38m 1 Stop (CMH)
      • BOSBoston Logan International Airport 07:00 - ORD 12:38 6h 38m 1 Stop (CMH) Columbus
      • BOSBoston Logan International Airport 07:00
        CMHColumbus Port Columbus Intl Airport 12:11
      • CMHColumbus Port Columbus Intl Airport 09:30
        ORDChicago O'Hare International Airport 12:38
      • 6h 38m (2h 41m)
      • 1 Stop CMH · Columbus 2h 41m
      • American Airlines (AA 4389)Embraer Emb 175
        American Airlines (AA 3955)Embraer 170
      • American Airlines (AA 4389)
        • -
        • -
        • -
        • T
        • -
        • -
        • S
      • 07:01 BOS
        11:02 ORD
        5Hrs, 01m 1 Stop (DCA)
      • BOSBoston Logan International Airport 07:01 - ORD 11:02 5h 01m 1 Stop (DCA) Washington
      • BOSBoston Logan International Airport 07:01
        DCAWashington Ronald Reagan National Airport 09:44
      • DCAWashington Ronald Reagan National Airport 08:54
        ORDChicago O'Hare International Airport 11:02
      • 5h 01m (50m)
      • 1 Stop DCA · Washington 50m
      • American Airlines (AA 3261)Airbus
        American Airlines (AA 1200)Airbus
      • American Airlines (AA 3261)
        • -
        • -
        • -
        • T
        • F
        • -
        • -
      • 07:05 BOS
        11:45 MDW
        5Hrs, 40m 1 Stop (STL)
      • BOSBoston Logan International Airport 07:05 - MDW 11:45 5h 40m 1 Stop (STL) Saint Louis
      • BOSBoston Logan International Airport 07:05
        STLSt Louis Lambert Intl Airport 10:35
      • STLSt Louis Lambert Intl Airport 09:15
        MDWChicago Midway Airport 11:45
      • 5h 40m (1h 20m)
      • 1 Stop STL · Saint Louis 1h 20m
      • Southwest Airlines (WN 936)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 2364)Boeing 737 800
      • Southwest Airlines (WN 936)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • 07:30 BOS
        11:38 ORD
        5Hrs, 08m 1 Stop (EWR)
      • BOSBoston Logan International Airport 07:30 - ORD 11:38 5h 08m 1 Stop (EWR) New York City
      • BOSBoston Logan International Airport 07:30
        EWRNewark Liberty International Airport 10:00
      • EWRNewark Liberty International Airport 08:58
        ORDChicago O'Hare International Airport 11:38
      • 5h 08m (1h 02m)
      • 1 Stop EWR · New York City 1h 02m
      • United Airlines (UA 570)Airbus
        United Airlines (UA 1525)Boeing 737 900
      • United Airlines (UA 570)
        • -
        • -
        • -
        • -
        • F
        • -
        • S
      • 07:30 BOS
        13:00 ORD
        6Hrs, 30m 1 Stop (EWR)
      • BOSBoston Logan International Airport 07:30 - ORD 13:00 6h 30m 1 Stop (EWR) New York City
      • BOSBoston Logan International Airport 07:30
        EWRNewark Liberty International Airport 11:30
      • EWRNewark Liberty International Airport 08:58
        ORDChicago O'Hare International Airport 13:00
      • 6h 30m (2h 32m)
      • 1 Stop EWR · New York City 2h 32m
      • United Airlines (UA 570)Boeing 737 900
        United Airlines (UA 1875)Boeing Dreamliner Series 10
      • United Airlines (UA 570)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • 07:30 BOS
        11:38 ORD
        5Hrs, 08m 1 Stop (EWR)
      • BOSBoston Logan International Airport 07:30 - ORD 11:38 5h 08m 1 Stop (EWR) New York City
      • BOSBoston Logan International Airport 07:30
        EWRNewark Liberty International Airport 10:00
      • EWRNewark Liberty International Airport 08:58
        ORDChicago O'Hare International Airport 11:38
      • 5h 08m (1h 02m)
      • 1 Stop EWR · New York City 1h 02m
      • United Airlines (UA 570)Airbus
        United Airlines (UA 1525)Boeing 737 Max 8 Passenger
      • United Airlines (UA 570)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 07:30 BOS
        13:15 ORD
        6Hrs, 45m 1 Stop (EWR)
      • BOSBoston Logan International Airport 07:30 - ORD 13:15 6h 45m 1 Stop (EWR) New York City
      • BOSBoston Logan International Airport 07:30
        EWRNewark Liberty International Airport 11:37
      • EWRNewark Liberty International Airport 08:58
        ORDChicago O'Hare International Airport 13:15
      • 6h 45m (2h 39m)
      • 1 Stop EWR · New York City 2h 39m
      • United Airlines (UA 570)Airbus
        United Airlines (UA 1875)Boeing 757 200 Series
      • United Airlines (UA 570)
        • -
        • -
        • -
        • -
        • F
        • S
        • S
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      What’s the fastest flight time from Boston to Chicago?

      The fastest flight time for direct flights from Boston to Chicago is 2 hours 45 minutes. Check latest flight schedules & prices on Wego.

      What’s the most popular airline flying from Boston to Chicago?

      The most popular airline flying from Boston to Chicago is United Airlines. Find the latest flight deals on Wego.

      How far is Chicago from Boston?

      The flight distance between Boston and Chicago is 1366km. Check all available flights on Wego.

      When is the earliest and latest flight of the day?

      The earliest flight of the day departs at 05:00. The last flight of the day departs at 19:00. See the full list of flight times on Wego.

      How many airlines offer direct flights from Boston to Chicago?

      There are 4 airlines that offer direct flights from Boston to Chicago. Find out the list of airlines on Wego.

      All Airports in Boston

      Boston Logan International Airport BOS

      Popular Airlines Flying From Boston to Chicago

      United Airlines ‏()
      Southwest Airlines ‏()

      Popular Destinations From Chicago

      Popular Destinations From Boston

      Popular Hotels in Chicago

      Hotels In Popular Destinations