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

Find cheap airline tickets from Chicago to Boston by date

  • any
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • July 2019
  • August 2019
  • September 2019
  • October 2019
  • November 2019
  • December 2019
  • January 2020
  • February 2020
  • any
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • July 2019
  • August 2019
  • September 2019
  • October 2019
  • November 2019
  • December 2019
  • January 2020
  • February 2020
  • price
  • month of departure
  • month of return
$112
outward: May 8, 2019
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
inbound: May 14, 2019
6:36p BOS » 9:28p ORD
Spirit Airlines direct (2h52m)
$112
outward: May 30, 2019
9:10p ORD » 11:46p BOS
Spirit Airlines direct (2h36m)
inbound: Jun 3, 2019
6:10p BOS » 9:02p ORD
Spirit Airlines direct (2h52m)
$113
outward: May 30, 2019
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
inbound: Jun 3, 2019
6:36p BOS » 9:28p ORD
Spirit Airlines direct (2h52m)
$113
outward: May 30, 2019
9:10p ORD » 11:46p BOS
Spirit Airlines direct (2h36m)
inbound: Jun 3, 2019
6:10p BOS » 9:02p ORD
Spirit Airlines direct (2h52m)
$113
outward: May 30, 2019
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
inbound: Jun 3, 2019
6:36p BOS » 9:28p ORD
Spirit Airlines direct (2h52m)
$113
outward: May 30, 2019
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
inbound: Jun 3, 2019
6:36p BOS » 9:28p ORD
Spirit Airlines direct (2h52m)
$113
outward: May 30, 2019
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
inbound: Jun 3, 2019
6:36p BOS » 9:28p ORD
Spirit Airlines direct (2h52m)
$113
outward: May 8, 2019
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
inbound: May 15, 2019
6:36p BOS » 9:28p ORD
Spirit Airlines direct (2h52m)
$114
outward: May 30, 2019
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
inbound: Jun 3, 2019
6:36p BOS » 9:28p ORD
Spirit Airlines direct (2h52m)
$114
outward: May 9, 2019
1:00p ORD » 3:14p BOS
American Airlines direct (2h14m)
inbound: May 12, 2019
11:00a BOS » 1:44p ORD
American Airlines direct (2h44m)
$116
outward: May 30, 2019
5:19a ORD » 7:37a BOS
American Airlines direct (2h18m)
inbound: Jun 19, 2019
11:00a BOS » 1:41p ORD
American Airlines direct (2h41m)
$128
outward: May 2, 2019
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
inbound: May 5, 2019
12:00p BOS » 2:48p ORD
JetBlue direct (2h48m)
$131
outward: May 30, 2019
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
inbound: Jun 3, 2019
6:36p BOS » 9:28p ORD
Spirit Airlines direct (2h52m)
$131
outward: May 30, 2019
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
inbound: Jun 3, 2019
6:36p BOS » 9:28p ORD
Spirit Airlines direct (2h52m)
$133
outward: May 2, 2019
9:10p ORD » 11:37p BOS
Spirit Airlines direct (2h27m)
inbound: May 5, 2019
12:00p BOS » 2:48p ORD
JetBlue direct (2h48m)
$144
outward: May 30, 2019
1:00p ORD » 3:14p BOS
American Airlines direct (2h14m)
inbound: Jun 4, 2019
2:18a BOS » 5:10a ORD
American Airlines direct (2h52m)
$146
outward: Jul 2, 2019
9:12p ORD » 11:41p BOS
Spirit Airlines direct (2h29m)
inbound: Jul 9, 2019
2:55a BOS » 5:44a ORD
JetBlue direct (2h49m)
$147
outward: Jul 2, 2019
9:12p ORD » 11:41p BOS
Spirit Airlines direct (2h29m)
inbound: Jul 9, 2019
2:55a BOS » 5:44a ORD
JetBlue direct (2h49m)
$147
outward: Jul 2, 2019
9:12p ORD » 11:41p BOS
Spirit Airlines direct (2h29m)
inbound: Jul 9, 2019
2:55a BOS » 5:44a ORD
JetBlue direct (2h49m)
$151
outward: Oct 11, 2019
3:45p ORD » 6:20p BOS
Delta Air Lines direct (2h35m)
inbound: Oct 17, 2019
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$154
outward: Mar 27, 2019
4:20a MDW » 6:35a BOS
Southwest Airlines direct (2h15m)
inbound: Mar 29, 2019
10:00a BOS » 12:50p MDW
Southwest Airlines direct (2h50m)
$154
outward: Mar 27, 2019
4:20a MDW » 6:35a BOS
Southwest Airlines direct (2h15m)
inbound: Mar 29, 2019
10:00a BOS » 12:50p MDW
Southwest Airlines direct (2h50m)
$154
outward: Mar 27, 2019
4:20a MDW » 6:35a BOS
Southwest Airlines direct (2h15m)
inbound: Mar 29, 2019
10:00a BOS » 12:50p MDW
Southwest Airlines direct (2h50m)
$154
outward: Mar 27, 2019
4:20a MDW » 6:35a BOS
Southwest Airlines direct (2h15m)
inbound: Mar 29, 2019
10:00a BOS » 12:50p MDW
Southwest Airlines direct (2h50m)
$154
outward: Jul 2, 2019
9:12p ORD » 11:41p BOS
Spirit Airlines direct (2h29m)
inbound: Jul 9, 2019
2:55a BOS » 5:44a ORD
JetBlue direct (2h49m)
$156
outward: Jun 20, 2019
2:15p ORD » 4:32p BOS
American Airlines direct (2h17m)
inbound: Jun 25, 2019
2:25a BOS » 5:06a ORD
American Airlines direct (2h41m)
$158
outward: Jul 2, 2019
9:12p ORD » 11:41p BOS
Spirit Airlines direct (2h29m)
inbound: Jul 9, 2019
2:55a BOS » 5:44a ORD
JetBlue direct (2h49m)
$158
outward: May 30, 2019
1:00p ORD » 3:14p BOS
American Airlines direct (2h14m)
inbound: Jun 4, 2019
2:18a BOS » 5:10a ORD
American Airlines direct (2h52m)
$159
outward: Jul 2, 2019
12:45p ORD » 3:02p BOS
JetBlue direct (2h17m)
inbound: Jul 8, 2019
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$159
outward: Oct 11, 2019
3:45p ORD » 6:20p BOS
Delta Air Lines direct (2h35m)
inbound: Oct 17, 2019
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
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
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • July 2019
  • August 2019
  • September 2019
  • October 2019
  • November 2019
  • December 2019
  • January 2020
  • February 2020
  • all
  • American Airlines
  • Delta Air Lines
  • JetBlue
  • Spirit Airlines
  • United Airlines
Spirit Airlines
outbound: May 8, 2019
Spirit Airlines direct
return: May 15, 2019
Spirit Airlines direct
JetBlue
outbound: Jun 14, 2019
JetBlue direct
return: Jun 16, 2019
JetBlue direct
Delta Air Lines
outbound: May 8, 2019
Delta Air Lines 1 stop
return: May 15, 2019
Delta Air Lines 1 stop
American Airlines
outbound: Jun 14, 2019
American Airlines direct
return: Jun 16, 2019
American Airlines direct
United Airlines
outbound: Apr 19, 2019
United Airlines 1 stop
return: Apr 23, 2019
JetBlue direct

Travel tips for flights Chicago - Boston

Average flight duration: 2h32m (direct flight)

  • Arrival city:
  • Boston, USA
  • Airport(s):
  • Logan International Airport (BOS)
  • Manchester–Boston Regional Airport (MHT)
  • Local time:
  • Mar 21, 2019 3:52 AM, GMT-4
  • Weather:
  • min. 38ºF, max. 49ºF
  • Departure city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Mar 21, 2019 2:52 AM, GMT-5
  • Weather:
  • min. 32ºF, max. 41ºF