Fare Guide

Estimated lowest fares found within 7 days

Cheapest Airline Spirit Airlines

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

  • Spirit Airlines Spirit Airlines
  • Delta Air Lines Delta Air Lines
  • JetBlue Airways JetBlue Airways
  • American Airlines American Airlines
  • United Airlines United Airlines
  • Frontier Airlines Frontier Airlines
  • Sun Country Airlines Sun Country Airlines
  • Alaska Airlines Alaska Airlines
Cheapest Month June

Travel Period: May 2024 - April 2025

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

  • May 2024
  • Jun 2024
  • Jul 2024
  • Aug 2024
  • Sep 2024
  • Oct 2024
  • Nov 2024
  • Dec 2024
  • Jan 2025
  • Feb 2025
  • Mar 2025
  • Apr 2025
Cheapest Day of the Week Wednesday

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

  • Sun Sunday
  • Mon Monday
  • Tue Tuesday
  • Wed Wednesday
  • Thu Thursday
  • Fri Friday
  • Sat Saturday
Cheapest Time 9pm

The cheapest time of the day to fly from Chicago to Boston is in the evening.

Early Morning 12:01am - 06:00am
Morning 6:01am - 12:00pm
Afternoon 12:01pm - 6:00pm
Evening 6:01pm to 12:00am
12am
6am
12pm
6pm

Flight Schedules

Last Updated: Tue, 2 Apr, 2024

  • Depart Earliest
    • Earliest
    • Latest
  • Arrive
    • Earliest
    • Latest
  • Airline Filter by Airline
    All
  • Total Duration
    • Shortest
    • Longest
  • Stopover
    All
  • Availability
    • M
    • T
    • W
    • T
    • F
    • S
    • S
  • 19:15 - 22:30
    MDW - BOS
  • 19:15 (MDW)Chicago Midway Airport
  • 22:30 (BOS)Boston Logan International Airport
  • (WN 2383)Boeing 737 Max 8 Passenger
  • 2h 15m
  • Direct
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • Boeing 737 Max 8 Passenger
  • 19:15 - 22:47
    ORD - BOS
  • 19:15 (ORD)Chicago O'Hare International Airport
  • 22:47 (BOS)Boston Logan International Airport
  • Delta Air Lines (DL 2346)Airbus A220 100 Passenger
  • 2h 32m
  • Direct
    • M
    • T
    • W
    • T
    • F
    • -
    • S
  • Airbus A220 100 Passenger
  • 19:45 - 23:00
    MDW - BOS
  • 19:45 (MDW)Chicago Midway Airport
  • 23:00 (BOS)Boston Logan International Airport
  • (WN 2383)Boeing 737 800
  • 2h 15m
  • Direct
    • M
    • -
    • -
    • T
    • F
    • -
    • -
  • Boeing 737 800
  • 20:20 - 23:40
    ORD - BOS
  • 20:20 (ORD)Chicago O'Hare International Airport
  • 23:40 (BOS)Boston Logan International Airport
  • American Airlines (AA 2682)Boeing 737 800
  • 2h 20m
  • Direct
    • M
    • T
    • W
    • T
    • F
    • S
    • S
  • Boeing 737 800
  • 20:30 - 23:45
    MDW - BOS
  • 20:30 (MDW)Chicago Midway Airport
  • 23:45 (BOS)Boston Logan International Airport
  • (WN 2383)Boeing 737 800
  • 2h 15m
  • Direct
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • Boeing 737 800
  • 21:05 - 00:19+ 1
    ORD - BOS
  • 21:05 (ORD)Chicago O'Hare International Airport
  • 00:19 (BOS)Boston Logan International Airport + 1
  • United Airlines (UA 2627)Boeing 737 800
  • 2h 14m
  • Direct
    • M
    • T
    • W
    • T
    • F
    • S
    • S
  • Boeing 737 800
  • 06:15 - 09:30
    MDW - BOS
  • 06:15 (MDW)Chicago Midway Airport
  • 09:30 (BOS)Boston Logan International Airport
  • (WN 862)Boeing 737 Max 8 Passenger
  • 2h 15m
  • Direct
    • M
    • -
    • -
    • T
    • F
    • -
    • -
  • Boeing 737 Max 8 Passenger
  • 06:30 - 09:56
    ORD - BOS
  • 06:30 (ORD)Chicago O'Hare International Airport
  • 09:56 (BOS)Boston Logan International Airport
  • American Airlines (AA 3710)Embraer Emb 175
  • 2h 26m
  • Direct
    • M
    • T
    • W
    • T
    • F
    • S
    • S
  • Embraer Emb 175
  • 07:00 - 10:27
    ORD - BOS
  • 07:00 (ORD)Chicago O'Hare International Airport
  • 10:27 (BOS)Boston Logan International Airport
  • Delta Air Lines (DL 1411)Airbus A220 100 Passenger
  • 2h 27m
  • Direct
    • M
    • T
    • W
    • T
    • F
    • -
    • -
  • Airbus A220 100 Passenger
  • 07:00 - 10:27
    ORD - BOS
  • 07:00 (ORD)Chicago O'Hare International Airport
  • 10:27 (BOS)Boston Logan International Airport
  • Delta Air Lines (DL 1371)Airbus A220 100 Passenger
  • 2h 27m
  • Direct
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • Airbus A220 100 Passenger
  • 07:00 - 10:15
    MDW - BOS
  • 07:00 (MDW)Chicago Midway Airport
  • 10:15 (BOS)Boston Logan International Airport
  • (WN 862)Boeing 737 700
  • 2h 15m
  • Direct
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • Boeing 737 700
  • 07:15 - 10:30
    MDW - BOS
  • 07:15 (MDW)Chicago Midway Airport
  • 10:30 (BOS)Boston Logan International Airport
  • (WN 862)Boeing 737 Max 8 Passenger
  • 2h 15m
  • Direct
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • Boeing 737 Max 8 Passenger
  • 07:45 - 11:06
    ORD - BOS
  • 07:45 (ORD)Chicago O'Hare International Airport
  • 11:06 (BOS)Boston Logan International Airport
  • United Airlines (UA 1803)Boeing 737 800
  • 2h 21m
  • Direct
    • M
    • T
    • W
    • T
    • F
    • S
    • S
  • Boeing 737 800
  • 08:20 - 11:38
    ORD - BOS
  • 08:20 (ORD)Chicago O'Hare International Airport
  • 11:38 (BOS)Boston Logan International Airport
  • American Airlines (AA 1457)Boeing 737 800
  • 2h 18m
  • Direct
    • M
    • T
    • W
    • T
    • F
    • S
    • S
  • Boeing 737 800
  • 08:50 - 12:10
    MDW - BOS
  • 08:50 (MDW)Chicago Midway Airport
  • 12:10 (BOS)Boston Logan International Airport
  • (WN 5802)Boeing 737 Max 8 Passenger
  • 2h 20m
  • Direct
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • Boeing 737 Max 8 Passenger
  • 08:52 - 12:11
    ORD - BOS
  • 08:52 (ORD)Chicago O'Hare International Airport
  • 12:11 (BOS)Boston Logan International Airport
  • United Airlines (UA 1495)Boeing 737 700
  • 2h 19m
  • Direct
    • M
    • T
    • W
    • T
    • F
    • -
    • S
  • Boeing 737 700
  • 09:00 - 12:15
    MDW - BOS
  • 09:00 (MDW)Chicago Midway Airport
  • 12:15 (BOS)Boston Logan International Airport
  • (WN 5802)Boeing 737 800
  • 2h 15m
  • Direct
    • M
    • -
    • -
    • T
    • F
    • -
    • -
  • Boeing 737 800
  • 09:55 - 13:13
    ORD - BOS
  • 09:55 (ORD)Chicago O'Hare International Airport
  • 13:13 (BOS)Boston Logan International Airport
  • American Airlines (AA 1479)Boeing 737 800
  • 2h 18m
  • Direct
    • M
    • T
    • W
    • T
    • F
    • S
    • S
  • Boeing 737 800
  • 10:15 - 13:42
    ORD - BOS
  • 10:15 (ORD)Chicago O'Hare International Airport
  • 13:42 (BOS)Boston Logan International Airport
  • Delta Air Lines (DL 1088)Airbus A220 100 Passenger
  • 2h 27m
  • Direct
    • M
    • T
    • W
    • T
    • F
    • -
    • S
  • Airbus A220 100 Passenger
  • 10:40 - 13:59
    ORD - BOS
  • 10:40 (ORD)Chicago O'Hare International Airport
  • 13:59 (BOS)Boston Logan International Airport
  • JetBlue Airways (B6 312)Embraer Emb E90
  • 2h 19m
  • Direct
    • M
    • T
    • W
    • T
    • F
    • S
    • S
  • Embraer Emb E90
  • 10:51 - 14:11
    ORD - BOS
  • 10:51 (ORD)Chicago O'Hare International Airport
  • 14:11 (BOS)Boston Logan International Airport
  • United Airlines (UA 691)Boeing 737 800
  • 2h 20m
  • Direct
    • M
    • T
    • W
    • T
    • F
    • S
    • S
  • Boeing 737 800
  • 11:35 - 14:55
    MDW - BOS
  • 11:35 (MDW)Chicago Midway Airport
  • 14:55 (BOS)Boston Logan International Airport
  • (WN 745)Boeing 737 Max 8 Passenger
  • 2h 20m
  • Direct
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • Boeing 737 Max 8 Passenger
  • 12:00 - 15:27
    ORD - BOS
  • 12:00 (ORD)Chicago O'Hare International Airport
  • 15:27 (BOS)Boston Logan International Airport
  • Delta Air Lines (DL 1154)Airbus A220 100 Passenger
  • 2h 27m
  • Direct
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • Airbus A220 100 Passenger
  • 12:30 - 15:50
    MDW - BOS
  • 12:30 (MDW)Chicago Midway Airport
  • 15:50 (BOS)Boston Logan International Airport
  • (WN 2383)Boeing 737 800
  • 2h 20m
  • Direct
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • Boeing 737 800
  • 13:20 - 16:39
    ORD - BOS
  • 13:20 (ORD)Chicago O'Hare International Airport
  • 16:39 (BOS)Boston Logan International Airport
  • American Airlines (AA 1485)Boeing 737 800
  • 2h 19m
  • Direct
    • M
    • T
    • W
    • T
    • F
    • S
    • S
  • Boeing 737 800
  • 13:55 - 17:15
    MDW - BOS
  • 13:55 (MDW)Chicago Midway Airport
  • 17:15 (BOS)Boston Logan International Airport
  • (WN 745)Boeing 737 Max 8 Passenger
  • 2h 20m
  • Direct
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • Boeing 737 Max 8 Passenger
  • 14:00 - 17:20
    ORD - BOS
  • 14:00 (ORD)Chicago O'Hare International Airport
  • 17:20 (BOS)Boston Logan International Airport
  • United Airlines (UA 378)Boeing 737 900
  • 2h 20m
  • Direct
    • M
    • T
    • W
    • T
    • F
    • S
    • S
  • Boeing 737 900
  • 14:15 - 17:47
    ORD - BOS
  • 14:15 (ORD)Chicago O'Hare International Airport
  • 17:47 (BOS)Boston Logan International Airport
  • Delta Air Lines (DL 1429)Airbus A220 100 Passenger
  • 2h 32m
  • Direct
    • M
    • T
    • W
    • T
    • F
    • -
    • S
  • Airbus A220 100 Passenger
  • 16:00 - 19:15
    MDW - BOS
  • 16:00 (MDW)Chicago Midway Airport
  • 19:15 (BOS)Boston Logan International Airport
  • (WN 745)Boeing 737 700
  • 2h 15m
  • Direct
    • M
    • -
    • -
    • T
    • F
    • -
    • -
  • Boeing 737 700
  • 16:50 - 20:06
    ORD - BOS
  • 16:50 (ORD)Chicago O'Hare International Airport
  • 20:06 (BOS)Boston Logan International Airport
  • American Airlines (AA 1461)Boeing 737 800
  • 2h 16m
  • Direct
    • M
    • T
    • W
    • T
    • F
    • S
    • S
  • Boeing 737 800
  • 17:05 - 20:20
    MDW - BOS
  • 17:05 (MDW)Chicago Midway Airport
  • 20:20 (BOS)Boston Logan International Airport
  • (WN 745)Boeing 737 800
  • 2h 15m
  • Direct
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • Boeing 737 800
  • 17:30 - 21:00
    ORD - BOS
  • 17:30 (ORD)Chicago O'Hare International Airport
  • 21:00 (BOS)Boston Logan International Airport
  • Delta Air Lines (DL 2427)Airbus A220 100 Passenger
  • 2h 30m
  • Direct
    • M
    • T
    • W
    • T
    • F
    • S
    • S
  • Airbus A220 100 Passenger
  • 17:50 - 21:10
    MDW - BOS
  • 17:50 (MDW)Chicago Midway Airport
  • 21:10 (BOS)Boston Logan International Airport
  • (WN 998)Boeing 737 800
  • 2h 20m
  • Direct
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • Boeing 737 800
  • 17:57 - 21:11
    ORD - BOS
  • 17:57 (ORD)Chicago O'Hare International Airport
  • 21:11 (BOS)Boston Logan International Airport
  • United Airlines (UA 1568)Boeing 737 900
  • 2h 14m
  • Direct
    • M
    • T
    • W
    • T
    • F
    • S
    • S
  • Boeing 737 900
  • 18:25 - 21:53
    ORD - BOS
  • 18:25 (ORD)Chicago O'Hare International Airport
  • 21:53 (BOS)Boston Logan International Airport
  • American Airlines (AA 1033)Boeing 737 Max 8 Passenger
  • 2h 28m
  • Direct
    • M
    • T
    • W
    • T
    • F
    • S
    • S
  • Boeing 737 Max 8 Passenger

Connecting Flights

  • 05:55 - 07:05
    MDW - STL
    08:00 - 11:35
    STL - BOS
  • 05:55 (MDW)Chicago Midway Airport
    08:00 (STL)St Louis Lambert Intl Airport
  • 07:05 (STL)St Louis Lambert Intl Airport
    11:35 (BOS)Boston Logan International Airport
  • (WN 5846)Boeing 737 Max 8 Passenger
    (WN 949)Boeing 737 Max 8 Passenger
  • 4h 40m (55m)
  • STL Saint Louis 55m
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • 07:15 - 08:45
    ORD - BNA
    10:10 - 13:40
    BNA - BOS
  • 07:15 (ORD)Chicago O'Hare International Airport
    10:10 (BNA)Nashville Airport
  • 08:45 (BNA)Nashville Airport
    13:40 (BOS)Boston Logan International Airport
  • (WN 658)Boeing 737 Max 8 Passenger
    (WN 1535)Boeing 737 Max 8 Passenger
  • 5h 25m (1h 25m)
  • BNA Nashville 1h 25m
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • 08:00 - 09:25
    MDW - BNA
    10:25 - 13:55
    BNA - BOS
  • 08:00 (MDW)Chicago Midway Airport
    10:25 (BNA)Nashville Airport
  • 09:25 (BNA)Nashville Airport
    13:55 (BOS)Boston Logan International Airport
  • (WN 433)Boeing 737 Max 8 Passenger
    (WN 1535)Boeing 737 Max 8 Passenger
  • 4h 55m (1h)
  • BNA Nashville 1h
    • M
    • -
    • -
    • T
    • F
    • -
    • -
  • 08:15 - 11:10
    MDW - BWI
    12:30 - 13:55
    BWI - BOS
  • 08:15 (MDW)Chicago Midway Airport
    12:30 (BWI)Baltimore Washington International Airport
  • 11:10 (BWI)Baltimore Washington International Airport
    13:55 (BOS)Boston Logan International Airport
  • (WN 5903)Boeing 737 800
    (WN 5279)Boeing 737 800
  • 4h 40m (1h 20m)
  • BWI Baltimore 1h 20m
    • M
    • -
    • -
    • T
    • F
    • -
    • -
  • 08:35 - 11:30
    MDW - BWI
    14:10 - 15:35
    BWI - BOS
  • 08:35 (MDW)Chicago Midway Airport
    14:10 (BWI)Baltimore Washington International Airport
  • 11:30 (BWI)Baltimore Washington International Airport
    15:35 (BOS)Boston Logan International Airport
  • (WN 5903)Boeing 737 700
    (WN 5887)Boeing 737 700
  • 6h (2h 40m)
  • BWI Baltimore 2h 40m
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • 10:05 - 11:30
    MDW - BNA
    12:25 - 15:55
    BNA - BOS
  • 10:05 (MDW)Chicago Midway Airport
    12:25 (BNA)Nashville Airport
  • 11:30 (BNA)Nashville Airport
    15:55 (BOS)Boston Logan International Airport
  • (WN 433)Boeing 737 800
    (WN 1535)Boeing 737 Max 8 Passenger
  • 4h 50m (55m)
  • BNA Nashville 55m
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • 10:35 - 13:20
    MDW - BWI
    14:10 - 15:35
    BWI - BOS
  • 10:35 (MDW)Chicago Midway Airport
    14:10 (BWI)Baltimore Washington International Airport
  • 13:20 (BWI)Baltimore Washington International Airport
    15:35 (BOS)Boston Logan International Airport
  • (WN 575)Boeing 737 Max 8 Passenger
    (WN 5887)Boeing 737 700
  • 4h (50m)
  • BWI Baltimore 50m
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • 11:25 - 12:35
    MDW - STL
    14:55 - 18:30
    STL - BOS
  • 11:25 (MDW)Chicago Midway Airport
    14:55 (STL)St Louis Lambert Intl Airport
  • 12:35 (STL)St Louis Lambert Intl Airport
    18:30 (BOS)Boston Logan International Airport
  • (WN 3021)Boeing 737 700
    (WN 186)Boeing 737 800
  • 6h 05m (2h 20m)
  • STL Saint Louis 2h 20m
    • M
    • -
    • -
    • T
    • F
    • -
    • -
  • 11:25 - 14:15
    ORD - BWI
    15:20 - 16:50
    BWI - BOS
  • 11:25 (ORD)Chicago O'Hare International Airport
    15:20 (BWI)Baltimore Washington International Airport
  • 14:15 (BWI)Baltimore Washington International Airport
    16:50 (BOS)Boston Logan International Airport
  • (WN 5932)Boeing 737 700
    (WN 735)Boeing 737 800
  • 4h 25m (1h 05m)
  • BWI Baltimore 1h 05m
    • M
    • -
    • -
    • T
    • F
    • -
    • -
  • 11:25 - 14:15
    ORD - BWI
    17:05 - 18:35
    BWI - BOS
  • 11:25 (ORD)Chicago O'Hare International Airport
    17:05 (BWI)Baltimore Washington International Airport
  • 14:15 (BWI)Baltimore Washington International Airport
    18:35 (BOS)Boston Logan International Airport
  • (WN 5932)Boeing 737 700
    (WN 671)Boeing 737 800
  • 6h 10m (2h 50m)
  • BWI Baltimore 2h 50m
    • M
    • -
    • -
    • T
    • F
    • -
    • -
  • 12:05 - 13:15
    MDW - STL
    14:05 - 17:35
    STL - BOS
  • 12:05 (MDW)Chicago Midway Airport
    14:05 (STL)St Louis Lambert Intl Airport
  • 13:15 (STL)St Louis Lambert Intl Airport
    17:35 (BOS)Boston Logan International Airport
  • (WN 3279)Boeing 737 700
    (WN 186)Boeing 737 Max 8 Passenger
  • 4h 30m (50m)
  • STL Saint Louis 50m
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • 12:15 - 15:05
    ORD - BWI
    16:40 - 18:05
    BWI - BOS
  • 12:15 (ORD)Chicago O'Hare International Airport
    16:40 (BWI)Baltimore Washington International Airport
  • 15:05 (BWI)Baltimore Washington International Airport
    18:05 (BOS)Boston Logan International Airport
  • (WN 5932)Boeing 737 800
    (WN 671)Boeing 737 800
  • 4h 50m (1h 35m)
  • BWI Baltimore 1h 35m
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • 12:35 - 15:25
    MDW - BWI
    17:05 - 18:35
    BWI - BOS
  • 12:35 (MDW)Chicago Midway Airport
    17:05 (BWI)Baltimore Washington International Airport
  • 15:25 (BWI)Baltimore Washington International Airport
    18:35 (BOS)Boston Logan International Airport
  • (WN 1015)Boeing 737 Max 8 Passenger
    (WN 671)Boeing 737 800
  • 5h (1h 40m)
  • BWI Baltimore 1h 40m
    • M
    • -
    • -
    • T
    • F
    • -
    • -
  • 12:50 - 15:40
    MDW - BWI
    17:35 - 19:05
    BWI - BOS
  • 12:50 (MDW)Chicago Midway Airport
    17:35 (BWI)Baltimore Washington International Airport
  • 15:40 (BWI)Baltimore Washington International Airport
    19:05 (BOS)Boston Logan International Airport
  • (WN 1015)Boeing 737 800
    (WN 1004)Boeing 737 Max 8 Passenger
  • 5h 15m (1h 55m)
  • BWI Baltimore 1h 55m
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • 13:00 - 14:25
    MDW - BNA
    16:00 - 19:30
    BNA - BOS
  • 13:00 (MDW)Chicago Midway Airport
    16:00 (BNA)Nashville Airport
  • 14:25 (BNA)Nashville Airport
    19:30 (BOS)Boston Logan International Airport
  • (WN 2942)Boeing 737 Max 8 Passenger
    (WN 5459)Boeing 737 Max 8 Passenger
  • 5h 30m (1h 35m)
  • BNA Nashville 1h 35m
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • 13:45 - 16:35
    MDW - BWI
    18:10 - 19:40
    BWI - BOS
  • 13:45 (MDW)Chicago Midway Airport
    18:10 (BWI)Baltimore Washington International Airport
  • 16:35 (BWI)Baltimore Washington International Airport
    19:40 (BOS)Boston Logan International Airport
  • (WN 1015)Boeing 737 Max 8 Passenger
    (WN 1004)Boeing 737 Max 8 Passenger
  • 4h 55m (1h 35m)
  • BWI Baltimore 1h 35m
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • 13:55 - 15:05
    MDW - STL
    17:10 - 20:40
    STL - BOS
  • 13:55 (MDW)Chicago Midway Airport
    17:10 (STL)St Louis Lambert Intl Airport
  • 15:05 (STL)St Louis Lambert Intl Airport
    20:40 (BOS)Boston Logan International Airport
  • (WN 5388)Boeing 737 700
    (WN 186)Boeing 737 Max 8 Passenger
  • 5h 45m (2h 05m)
  • STL Saint Louis 2h 05m
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • 14:50 - 17:40
    MDW - BWI
    19:40 - 21:05
    BWI - BOS
  • 14:50 (MDW)Chicago Midway Airport
    19:40 (BWI)Baltimore Washington International Airport
  • 17:40 (BWI)Baltimore Washington International Airport
    21:05 (BOS)Boston Logan International Airport
  • (WN 1833)Boeing 737 700
    (WN 5824)Boeing 737 800
  • 5h 15m (2h)
  • BWI Baltimore 2h
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • 16:30 - 19:15
    MDW - BWI
    21:55 - 23:20
    BWI - BOS
  • 16:30 (MDW)Chicago Midway Airport
    21:55 (BWI)Baltimore Washington International Airport
  • 19:15 (BWI)Baltimore Washington International Airport
    23:20 (BOS)Boston Logan International Airport
  • (WN 1833)Boeing 737 Max 8 Passenger
    (WN 738)Boeing 737 800
  • 5h 50m (2h 40m)
  • BWI Baltimore 2h 40m
    • M
    • -
    • -
    • T
    • F
    • -
    • -
  • 17:15 - 20:00
    MDW - BWI
    21:50 - 23:15
    BWI - BOS
  • 17:15 (MDW)Chicago Midway Airport
    21:50 (BWI)Baltimore Washington International Airport
  • 20:00 (BWI)Baltimore Washington International Airport
    23:15 (BOS)Boston Logan International Airport
  • (WN 1833)Boeing 737 800
    (WN 738)Boeing 737 Max 8 Passenger
  • 5h (1h 50m)
  • BWI Baltimore 1h 50m
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • 17:25 - 20:20
    ORD - BWI
    21:55 - 23:20
    BWI - BOS
  • 17:25 (ORD)Chicago O'Hare International Airport
    21:55 (BWI)Baltimore Washington International Airport
  • 20:20 (BWI)Baltimore Washington International Airport
    23:20 (BOS)Boston Logan International Airport
  • (WN 1773)Boeing 737 800
    (WN 738)Boeing 737 800
  • 4h 55m (1h 35m)
  • BWI Baltimore 1h 35m
    • M
    • -
    • -
    • T
    • F
    • -
    • -
  • 18:25 - 19:50+ 1
    MDW - BNA
    21:15 - 00:45+ 1
    BNA - BOS
  • 18:25 (MDW)Chicago Midway Airport
    21:15 (BNA)Nashville Airport
  • 19:50 (BNA)Nashville Airport + 1
    00:45 (BOS)Boston Logan International Airport
  • (WN 3207)Boeing 737 Max 8 Passenger
    (WN 1343)Boeing 737 Max 8 Passenger
  • 5h 20m (1h 25m)
  • BNA Nashville 1h 25m
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • 18:55 - 20:25+ 1
    ORD - BNA
    21:15 - 00:45+ 1
    BNA - BOS
  • 18:55 (ORD)Chicago O'Hare International Airport
    21:15 (BNA)Nashville Airport
  • 20:25 (BNA)Nashville Airport + 1
    00:45 (BOS)Boston Logan International Airport
  • (WN 5596)Boeing 737 Max 8 Passenger
    (WN 1343)Boeing 737 Max 8 Passenger
  • 4h 50m (50m)
  • BNA Nashville 50m
    • -
    • -
    • -
    • -
    • -
    • -
    • S
No Schedules Sorry, there are no schedules matching your filters. Try removing one. reset
What’s the fastest flight time from Chicago to Boston?

The fastest flight time for direct flights from Chicago to Boston is 2 hours 14 minutes. Check latest flight schedules & prices on Wego.

How far is Boston from Chicago?

The flight distance between Chicago and Boston 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 05:55. The last flight of the day departs at 19:15. See the full list of flight times on Wego.

How many airlines offer direct flights from Chicago to Boston?

There are 5 airlines that offer direct flights from Chicago to Boston. Find out the list of airlines on Wego.