Take off on cheap flights from Chicago to Boston, your adventure starts now!

Find cheap airline tickets from Chicago to Boston by date

  • any
  • July 2021
  • August 2021
  • September 2021
  • October 2021
  • November 2021
  • December 2021
  • January 2022
  • February 2022
  • March 2022
  • April 2022
  • May 2022
  • June 2022
  • any
  • July 2021
  • August 2021
  • September 2021
  • October 2021
  • November 2021
  • December 2021
  • January 2022
  • February 2022
  • March 2022
  • April 2022
  • May 2022
  • June 2022
  • price
  • month of departure
  • month of return
$134
American Airlines outward: Nov 3, 2021
12:00p ORD » 2:14p BOS
American Airlines direct (2h14m)
American Airlines inbound: Nov 7, 2021
11:45a BOS » 2:45p ORD
American Airlines direct (3h)
$134
American Airlines outward: Nov 3, 2021
1:15p ORD » 3:32p BOS
American Airlines direct (2h17m)
American Airlines inbound: Nov 7, 2021
12:54p BOS » 3:57p ORD
American Airlines direct (3h03m)
$136
American Airlines outward: Nov 3, 2021
12:00p ORD » 2:14p BOS
American Airlines direct (2h14m)
American Airlines inbound: Nov 7, 2021
11:45a BOS » 2:45p ORD
American Airlines direct (3h)
$136
American Airlines outward: Nov 3, 2021
12:00p ORD » 2:14p BOS
American Airlines direct (2h14m)
American Airlines inbound: Nov 7, 2021
11:45a BOS » 2:45p ORD
American Airlines direct (3h)
$136
American Airlines outward: Nov 3, 2021
12:00p ORD » 2:14p BOS
American Airlines direct (2h14m)
American Airlines inbound: Nov 7, 2021
11:45a BOS » 2:45p ORD
American Airlines direct (3h)
$136
American Airlines outward: Nov 3, 2021
12:00p ORD » 2:14p BOS
American Airlines direct (2h14m)
American Airlines inbound: Nov 7, 2021
11:45a BOS » 2:45p ORD
American Airlines direct (3h)
$136
American Airlines outward: Nov 3, 2021
12:00p ORD » 2:14p BOS
American Airlines direct (2h14m)
American Airlines inbound: Nov 7, 2021
11:45a BOS » 2:45p ORD
American Airlines direct (3h)
$136
American Airlines outward: Nov 3, 2021
12:00p ORD » 2:14p BOS
American Airlines direct (2h14m)
American Airlines inbound: Nov 7, 2021
11:45a BOS » 2:45p ORD
American Airlines direct (3h)
$136
Delta Air Lines outward: Nov 3, 2021
12:00p ORD » 2:27p BOS
Delta Air Lines direct (2h27m)
Delta Air Lines inbound: Nov 8, 2021
2:30a BOS » 5:35a ORD
Delta Air Lines direct (3h05m)
$136
American Airlines outward: Nov 3, 2021
12:00p ORD » 2:14p BOS
American Airlines direct (2h14m)
American Airlines inbound: Nov 7, 2021
11:45a BOS » 2:45p ORD
American Airlines direct (3h)
$136
American Airlines outward: Nov 3, 2021
12:00p ORD » 2:14p BOS
American Airlines direct (2h14m)
American Airlines inbound: Nov 7, 2021
11:45a BOS » 2:45p ORD
American Airlines direct (3h)
$136
American Airlines outward: Nov 3, 2021
12:00p ORD » 2:14p BOS
American Airlines direct (2h14m)
American Airlines inbound: Nov 7, 2021
11:45a BOS » 2:45p ORD
American Airlines direct (3h)
$136
American Airlines outward: Nov 3, 2021
12:00p ORD » 2:14p BOS
American Airlines direct (2h14m)
American Airlines inbound: Nov 7, 2021
11:45a BOS » 2:45p ORD
American Airlines direct (3h)
$136
American Airlines outward: Nov 3, 2021
12:00p ORD » 2:14p BOS
American Airlines direct (2h14m)
American Airlines inbound: Nov 7, 2021
11:45a BOS » 2:45p ORD
American Airlines direct (3h)
$136
American Airlines outward: Nov 3, 2021
12:00p ORD » 2:14p BOS
American Airlines direct (2h14m)
American Airlines inbound: Nov 7, 2021
11:45a BOS » 2:45p ORD
American Airlines direct (3h)
$136
American Airlines outward: Nov 3, 2021
12:00p ORD » 2:14p BOS
American Airlines direct (2h14m)
American Airlines inbound: Nov 7, 2021
11:45a BOS » 2:45p ORD
American Airlines direct (3h)
$136
American Airlines outward: Nov 3, 2021
12:00p ORD » 2:14p BOS
American Airlines direct (2h14m)
American Airlines inbound: Nov 7, 2021
11:45a BOS » 2:45p ORD
American Airlines direct (3h)
$136
American Airlines outward: Nov 3, 2021
12:00p ORD » 2:14p BOS
American Airlines direct (2h14m)
American Airlines inbound: Nov 7, 2021
11:45a BOS » 2:45p ORD
American Airlines direct (3h)
$136
American Airlines outward: Nov 3, 2021
12:00p ORD » 2:14p BOS
American Airlines direct (2h14m)
American Airlines inbound: Nov 7, 2021
11:45a BOS » 2:45p ORD
American Airlines direct (3h)
$136
American Airlines outward: Nov 3, 2021
12:00p ORD » 2:14p BOS
American Airlines direct (2h14m)
American Airlines inbound: Nov 7, 2021
11:45a BOS » 2:45p ORD
American Airlines direct (3h)
$137
American Airlines outward: Nov 3, 2021
12:00p ORD » 2:14p BOS
American Airlines direct (2h14m)
American Airlines inbound: Nov 7, 2021
11:45a BOS » 2:45p ORD
American Airlines direct (3h)
$137
American Airlines outward: Nov 3, 2021
12:00p ORD » 2:14p BOS
American Airlines direct (2h14m)
American Airlines inbound: Nov 7, 2021
11:45a BOS » 2:45p ORD
American Airlines direct (3h)
$137
American Airlines outward: Nov 3, 2021
12:00p ORD » 2:14p BOS
American Airlines direct (2h14m)
American Airlines inbound: Nov 7, 2021
11:45a BOS » 2:45p ORD
American Airlines direct (3h)
$137
American Airlines outward: Nov 3, 2021
12:00p ORD » 2:14p BOS
American Airlines direct (2h14m)
American Airlines inbound: Nov 7, 2021
11:45a BOS » 2:45p ORD
American Airlines direct (3h)
$137
American Airlines outward: Nov 3, 2021
12:00p ORD » 2:14p BOS
American Airlines direct (2h14m)
American Airlines inbound: Nov 7, 2021
11:45a BOS » 2:45p ORD
American Airlines direct (3h)
$137
American Airlines outward: Nov 3, 2021
12:00p ORD » 2:14p BOS
American Airlines direct (2h14m)
American Airlines inbound: Nov 7, 2021
11:45a BOS » 2:45p ORD
American Airlines direct (3h)
$145
Delta Air Lines outward: Nov 3, 2021
12:00p ORD » 2:27p BOS
Delta Air Lines direct (2h27m)
Delta Air Lines inbound: Nov 8, 2021
2:30a BOS » 5:35a ORD
Delta Air Lines direct (3h05m)
$183
Spirit Airlines outward: Aug 19, 2021
10:56p ORD » 4:07a BOS
Spirit Airlines 1 stop (5h11m)
Spirit Airlines inbound: Aug 23, 2021
10:20p BOS » 7:19a ORD
Spirit Airlines 1 stop (8h59m)
$205
Spirit Airlines outward: Aug 13, 2021
1:30a ORD » 4:28p BOS
Spirit Airlines 1 stop (14h58m)
Spirit Airlines inbound: Aug 16, 2021
3:15a BOS » 3:12a ORD
Spirit Airlines 1 stop (23h57m)
$205
Spirit Airlines outward: Aug 13, 2021
1:30a ORD » 4:28p BOS
Spirit Airlines 1 stop (14h58m)
Spirit Airlines inbound: Aug 15, 2021
12:00p BOS » 2:49a ORD
Spirit Airlines 1 stop (14h49m)
Return
Departure
Choose when you'd like to depart to Boston (USA):
Find the cheapest Chicago Boston flight by browsing the dates below to find alternative flight prices found in the last days. To launch a flight search for Chicago - Boston with these new dates, click on an offer. Want to depart from another city? Choose:

Airlines operating flights from Chicago to Boston

  • any
  • July 2021
  • August 2021
  • September 2021
  • October 2021
  • November 2021
  • December 2021
  • January 2022
  • February 2022
  • March 2022
  • April 2022
  • May 2022
  • June 2022
  • all
  • Spirit Airlines
  • United Airlines
Spirit Airlines
outbound: Aug 19, 2021
Spirit Airlines 1 stop
return: Aug 23, 2021
Spirit Airlines 1 stop
United Airlines
outbound: Aug 19, 2021
United Airlines 1 stop
return: Aug 23, 2021
Spirit Airlines 1 stop

Travel tips for flights Chicago - Boston

Average flight duration: 15h16m (flight with stopovers)

  • Arrival city:
  • Boston, USA
  • Airport(s):
  • Logan International Airport (BOS)
  • Manchester–Boston Regional Airport (MHT)
  • Local time:
  • Jul 26, 2021 9:26 AM, GMT-4
  • Weather:
  • min. 67ºF, max. 89ºF
  • Departure city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Jul 26, 2021 8:26 AM, GMT-5
  • Weather:
  • min. 72ºF, max. 86ºF