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

Find cheap airline tickets from Chicago to Boston by date

  • any
  • June 2021
  • July 2021
  • August 2021
  • September 2021
  • October 2021
  • November 2021
  • December 2021
  • January 2022
  • February 2022
  • March 2022
  • April 2022
  • May 2022
  • any
  • June 2021
  • July 2021
  • August 2021
  • September 2021
  • October 2021
  • November 2021
  • December 2021
  • January 2022
  • February 2022
  • March 2022
  • April 2022
  • May 2022
  • price
  • month of departure
  • month of return
$131
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)
$132
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)
$132
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)
$132
American Airlines outward: Nov 3, 2021
12:00p ORD » 2:14p BOS
American Airlines direct (2h14m)
American Airlines inbound: Nov 7, 2021
3:00p BOS » 6:00p ORD
American Airlines direct (3h)
$132
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)
$132
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)
$132
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)
$132
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)
$132
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)
$132
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)
$132
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)
$132
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)
$132
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)
$132
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)
$132
American Airlines outward: Nov 3, 2021
12:00p ORD » 2:14p BOS
American Airlines direct (2h14m)
American Airlines inbound: Nov 7, 2021
12:54p BOS » 3:57p ORD
American Airlines direct (3h03m)
$133
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
Spirit Airlines outward: Nov 3, 2021
3:00p ORD » 5:18p BOS
Spirit Airlines direct (2h18m)
Spirit Airlines inbound: Nov 8, 2021
3:53a BOS » 6:26a ORD
Spirit Airlines direct (2h33m)
$137
Spirit Airlines outward: Nov 3, 2021
3:00p ORD » 5:18p BOS
Spirit Airlines direct (2h18m)
Spirit Airlines inbound: Nov 8, 2021
3:53a BOS » 6:26a ORD
Spirit Airlines direct (2h33m)
$137
Spirit Airlines outward: Nov 3, 2021
3:00p ORD » 5:18p BOS
Spirit Airlines direct (2h18m)
Spirit Airlines inbound: Nov 8, 2021
3:53a BOS » 6:26a ORD
Spirit Airlines direct (2h33m)
$137
Spirit Airlines outward: Nov 3, 2021
3:00p ORD » 5:18p BOS
Spirit Airlines direct (2h18m)
Spirit Airlines inbound: Nov 8, 2021
3:53a BOS » 6:26a ORD
Spirit Airlines direct (2h33m)
$138
Spirit Airlines outward: Nov 3, 2021
3:00p ORD » 5:18p BOS
Spirit Airlines direct (2h18m)
Spirit Airlines inbound: Nov 8, 2021
3:53a BOS » 6:26a ORD
Spirit Airlines direct (2h33m)
$140
United Airlines outward: Nov 3, 2021
1:45p ORD » 4:06p BOS
United Airlines direct (2h21m)
United Airlines inbound: Nov 7, 2021
3:30p BOS » 8:42p ORD
United Airlines 1 stop (5h12m)
$140
American Airlines outward: Nov 3, 2021
12:00p ORD » 2:14p BOS
American Airlines direct (2h14m)
United Airlines inbound: Nov 8, 2021
1:35a BOS » 6:12a ORD
United Airlines 1 stop (4h37m)
$140
United Airlines outward: Nov 3, 2021
4:51p ORD » 7:11p BOS
United Airlines direct (2h20m)
United Airlines inbound: Nov 7, 2021
3:30p BOS » 8:42p ORD
United Airlines 1 stop (5h12m)
$141
United Airlines outward: Nov 3, 2021
4:51p ORD » 7:11p BOS
United Airlines direct (2h20m)
United Airlines inbound: Nov 7, 2021
3:30p BOS » 8:42p ORD
United Airlines 1 stop (5h12m)
$141
United Airlines outward: Nov 3, 2021
4:51p ORD » 7:11p BOS
United Airlines direct (2h20m)
United Airlines inbound: Nov 7, 2021
12:00p BOS » 4:17p ORD
United Airlines 1 stop (4h17m)
$141
Delta Air Lines outward: Nov 3, 2021
12:00p ORD » 2:27p BOS
Delta Air Lines direct (2h27m)
Delta Air Lines inbound: Nov 7, 2021
11:21p BOS » 2:32a ORD
Delta Air Lines direct (3h11m)
$141
American Airlines outward: Nov 3, 2021
12:00p ORD » 2:14p BOS
American Airlines direct (2h14m)
United Airlines inbound: Nov 8, 2021
1:35a BOS » 6:12a ORD
United Airlines 1 stop (4h37m)
$170
Delta Air Lines outward: Jul 18, 2021
1:25a ORD » 6:59a BOS
Delta Air Lines 1 stop (5h34m)
Allegiant Air inbound: Jul 18, 2021
5:45p BOS » 12:18a MDW
Allegiant Air 1 stop (6h33m)
$175
JetBlue outward: Jul 17, 2021
1:00a ORD » 3:27a BOS
JetBlue direct (2h27m)
JetBlue inbound: Jul 25, 2021
1:30p BOS » 4:25p ORD
JetBlue direct (2h55m)
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
  • June 2021
  • July 2021
  • August 2021
  • September 2021
  • October 2021
  • November 2021
  • December 2021
  • January 2022
  • February 2022
  • March 2022
  • April 2022
  • May 2022
  • all
  • Spirit Airlines
  • United Airlines
Spirit Airlines
outbound: Jul 2, 2021
Spirit Airlines 1 stop
return: Jul 4, 2021
Spirit Airlines 1 stop
United Airlines
outbound: Jul 24, 2021
United Airlines direct
return: Jul 27, 2021
United Airlines 1 stop

Travel tips for flights Chicago - Boston

Average flight duration: 2h31m (direct flight)

  • Arrival city:
  • Boston, USA
  • Airport(s):
  • Logan International Airport (BOS)
  • Manchester–Boston Regional Airport (MHT)
  • Local time:
  • Jun 12, 2021 10:35 AM, GMT-4
  • Weather:
  • min. 57ºF, max. 75ºF
  • Departure city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Jun 12, 2021 9:35 AM, GMT-5
  • Weather:
  • min. 65ºF, max. 76ºF