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

Find cheap airline tickets from Chicago to Boston by date

  • any
  • April 2021
  • May 2021
  • June 2021
  • July 2021
  • August 2021
  • September 2021
  • October 2021
  • November 2021
  • December 2021
  • January 2022
  • February 2022
  • March 2022
  • any
  • April 2021
  • May 2021
  • June 2021
  • July 2021
  • August 2021
  • September 2021
  • October 2021
  • November 2021
  • December 2021
  • January 2022
  • February 2022
  • March 2022
  • price
  • month of departure
  • month of return
$90
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)
$92
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)
$92
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)
$93
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)
$93
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)
$93
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)
$98
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)
$98
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)
$98
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)
$99
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)
$99
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)
$106
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)
$106
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)
$107
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)
$108
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)
$136
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
American Airlines outward: Aug 27, 2021
1:00p ORD » 3:20p BOS
American Airlines direct (2h20m)
American Airlines inbound: Aug 30, 2021
12:00p BOS » 2:51p ORD
American Airlines direct (2h51m)
$146
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
4:00p BOS » 1:12a ORD
Delta Air Lines 1 stop (9h12m)
$146
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
4:00p BOS » 1:12a ORD
Delta Air Lines 1 stop (9h12m)
$154
Delta Air Lines outward: Nov 3, 2021
12:00p ORD » 2:27p BOS
Delta Air Lines direct (2h27m)
American Airlines inbound: Nov 7, 2021
11:45a BOS » 2:45p ORD
American Airlines direct (3h)
$154
Delta Air Lines outward: Aug 26, 2021
3:39p ORD » 9:55p BOS
Delta Air Lines 1 stop (6h16m)
Delta Air Lines inbound: Aug 29, 2021
6:25p BOS » 12:39a ORD
Delta Air Lines 1 stop (6h14m)
$154
Delta Air Lines outward: Aug 27, 2021
9:42p ORD » 1:52a BOS
Delta Air Lines 1 stop (4h10m)
Delta Air Lines inbound: Aug 30, 2021
8:38p BOS » 1:12a ORD
Delta Air Lines 1 stop (4h34m)
$154
Delta Air Lines outward: Aug 27, 2021
9:42p ORD » 1:52a BOS
Delta Air Lines 1 stop (4h10m)
Delta Air Lines inbound: Aug 30, 2021
8:38p BOS » 1:12a ORD
Delta Air Lines 1 stop (4h34m)
$155
Delta Air Lines outward: Aug 27, 2021
11:45p ORD » 4:28a BOS
Delta Air Lines 1 stop (4h43m)
Delta Air Lines inbound: Aug 30, 2021
8:38p BOS » 1:12a ORD
Delta Air Lines 1 stop (4h34m)
$155
JetBlue outward: Nov 3, 2021
12:00p ORD » 2:14p BOS
JetBlue direct (2h14m)
American Airlines inbound: Nov 7, 2021
1:00p BOS » 6:14p ORD
American Airlines 1 stop (5h14m)
$155
Delta Air Lines outward: Nov 3, 2021
12:00p ORD » 2:27p BOS
Delta Air Lines direct (2h27m)
American Airlines inbound: Nov 7, 2021
11:45a BOS » 2:45p ORD
American Airlines direct (3h)
$157
United Airlines outward: Aug 27, 2021
8:00p ORD » 1:55a BOS
United Airlines 1 stop (5h55m)
United Airlines inbound: Aug 31, 2021
1:35a BOS » 6:12a ORD
United Airlines 1 stop (4h37m)
$157
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
11:40a BOS » 4:09p ORD
Delta Air Lines 1 stop (4h29m)
$163
Delta Air Lines outward: Nov 3, 2021
12:00p ORD » 2:27p BOS
Delta Air Lines direct (2h27m)
American Airlines inbound: Nov 7, 2021
11:45a BOS » 2:45p ORD
American Airlines direct (3h)
$164
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)
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
  • April 2021
  • May 2021
  • June 2021
  • July 2021
  • August 2021
  • September 2021
  • October 2021
  • November 2021
  • December 2021
  • January 2022
  • February 2022
  • March 2022
  • all
  • Alaska Airlines
  • Spirit Airlines
  • United Airlines
Spirit Airlines
outbound: Aug 27, 2021
Spirit Airlines direct
return: Aug 30, 2021
Spirit Airlines direct
United Airlines
outbound: Aug 27, 2021
United Airlines 1 stop
return: Aug 30, 2021
United Airlines 1 stop
Alaska Airlines
outbound: Aug 27, 2021
Alaska Airlines 1 stop
return: Aug 30, 2021
Alaska Airlines 1 stop

Travel tips for flights Chicago - Boston

Average flight duration: 2h35m (direct flight)

  • Arrival city:
  • Boston, USA
  • Airport(s):
  • Logan International Airport (BOS)
  • Manchester–Boston Regional Airport (MHT)
  • Local time:
  • Apr 13, 2021 12:50 AM, GMT-4
  • Weather:
  • min. 44ºF, max. 52ºF
  • Departure city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Apr 12, 2021 11:50 PM, GMT-5
  • Weather:
  • min. 43ºF, max. 48ºF