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

Find cheap airline tickets from Chicago to Boston by date

  • any
  • May 2019
  • June 2019
  • July 2019
  • August 2019
  • September 2019
  • October 2019
  • November 2019
  • December 2019
  • January 2020
  • February 2020
  • March 2020
  • April 2020
  • any
  • May 2019
  • June 2019
  • July 2019
  • August 2019
  • September 2019
  • October 2019
  • November 2019
  • December 2019
  • January 2020
  • February 2020
  • March 2020
  • April 2020
  • price
  • month of departure
  • month of return
$118
Spirit Airlines outward: Nov 9, 2019
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Spirit Airlines inbound: Nov 13, 2019
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$118
Spirit Airlines outward: Sep 13, 2019
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Spirit Airlines inbound: Sep 16, 2019
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$118
Spirit Airlines outward: Sep 13, 2019
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Spirit Airlines inbound: Sep 16, 2019
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$118
Spirit Airlines outward: Nov 9, 2019
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Spirit Airlines inbound: Nov 13, 2019
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$119
Spirit Airlines outward: Nov 9, 2019
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Spirit Airlines inbound: Nov 13, 2019
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$119
Spirit Airlines outward: Nov 9, 2019
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Spirit Airlines inbound: Nov 13, 2019
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$125
Spirit Airlines outward: Jun 8, 2019
9:10p ORD » 11:46p BOS
Spirit Airlines direct (2h36m)
Spirit Airlines inbound: Jun 15, 2019
6:35p BOS » 9:26p ORD
Spirit Airlines direct (2h51m)
$135
Spirit Airlines outward: Nov 9, 2019
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Spirit Airlines inbound: Nov 13, 2019
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$135
Spirit Airlines outward: Nov 9, 2019
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Spirit Airlines inbound: Nov 13, 2019
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$135
Spirit Airlines outward: Nov 9, 2019
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Spirit Airlines inbound: Nov 13, 2019
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$135
Spirit Airlines outward: Nov 9, 2019
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Spirit Airlines inbound: Nov 13, 2019
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$143
Spirit Airlines outward: Nov 9, 2019
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Spirit Airlines inbound: Nov 13, 2019
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$143
Spirit Airlines outward: Nov 9, 2019
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Spirit Airlines inbound: Nov 13, 2019
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$143
Spirit Airlines outward: Nov 9, 2019
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Spirit Airlines inbound: Nov 13, 2019
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$143
Spirit Airlines outward: Nov 9, 2019
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Spirit Airlines inbound: Nov 13, 2019
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$143
Spirit Airlines outward: Nov 9, 2019
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Spirit Airlines inbound: Nov 13, 2019
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$143
Spirit Airlines outward: Nov 8, 2019
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Spirit Airlines inbound: Nov 11, 2019
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$144
Spirit Airlines outward: Nov 9, 2019
8:51p ORD » 11:21p BOS
Spirit Airlines direct (2h30m)
Spirit Airlines inbound: Nov 13, 2019
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$147
JetBlue outward: Nov 9, 2019
4:18p ORD » 6:30p BOS
JetBlue direct (2h12m)
JetBlue inbound: Nov 14, 2019
3:49a BOS » 6:40a ORD
JetBlue direct (2h51m)
$148
JetBlue outward: Dec 6, 2019
6:03p ORD » 8:17p BOS
JetBlue direct (2h14m)
JetBlue inbound: Dec 8, 2019
8:59p BOS » 12:00a ORD
JetBlue direct (3h01m)
$148
JetBlue outward: Jun 24, 2019
12:45p ORD » 3:02p BOS
JetBlue direct (2h17m)
JetBlue inbound: Aug 3, 2019
2:55a BOS » 5:44a ORD
JetBlue direct (2h49m)
$148
JetBlue outward: Jul 30, 2019
3:47a ORD » 6:13a BOS
JetBlue direct (2h26m)
JetBlue inbound: Aug 5, 2019
12:40p BOS » 3:34p ORD
JetBlue direct (2h54m)
$148
JetBlue outward: Nov 9, 2019
4:18p ORD » 6:30p BOS
JetBlue direct (2h12m)
JetBlue inbound: Nov 13, 2019
8:59p BOS » 12:00a ORD
JetBlue direct (3h01m)
$148
JetBlue outward: Nov 9, 2019
12:40p ORD » 2:52p BOS
JetBlue direct (2h12m)
JetBlue inbound: Nov 14, 2019
3:49a BOS » 6:40a ORD
JetBlue direct (2h51m)
$148
JetBlue outward: Nov 9, 2019
12:40p ORD » 2:52p BOS
JetBlue direct (2h12m)
JetBlue inbound: Nov 14, 2019
3:49a BOS » 6:40a ORD
JetBlue direct (2h51m)
$148
JetBlue outward: Nov 9, 2019
12:40p ORD » 2:52p BOS
JetBlue direct (2h12m)
JetBlue inbound: Nov 14, 2019
3:49a BOS » 6:40a ORD
JetBlue direct (2h51m)
$148
JetBlue outward: Nov 9, 2019
12:40p ORD » 2:52p BOS
JetBlue direct (2h12m)
JetBlue inbound: Nov 14, 2019
3:49a BOS » 6:40a ORD
JetBlue direct (2h51m)
$149
Spirit Airlines outward: Sep 4, 2019
9:12p ORD » 11:41p BOS
Spirit Airlines direct (2h29m)
Spirit Airlines inbound: Sep 11, 2019
6:45p BOS » 9:34p ORD
Spirit Airlines direct (2h49m)
$149
Spirit Airlines outward: Jun 11, 2019
9:10p ORD » 11:46p BOS
Spirit Airlines direct (2h36m)
Spirit Airlines inbound: Jun 19, 2019
6:35p BOS » 9:26p ORD
Spirit Airlines direct (2h51m)
$151
Spirit Airlines outward: Jun 8, 2019
9:10p ORD » 11:46p BOS
Spirit Airlines direct (2h36m)
Spirit Airlines inbound: Jun 15, 2019
6:35p BOS » 9:26p ORD
Spirit Airlines direct (2h51m)
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
  • May 2019
  • June 2019
  • July 2019
  • August 2019
  • September 2019
  • October 2019
  • November 2019
  • December 2019
  • January 2020
  • February 2020
  • March 2020
  • April 2020
  • all
  • American Airlines
  • Delta Air Lines
  • JetBlue
  • Southwest Airlines
  • Spirit Airlines
  • United Airlines
Spirit Airlines
outbound: Jul 5, 2019
Spirit Airlines direct
return: Jul 9, 2019
Spirit Airlines direct
Southwest Airlines
outbound: Jul 2, 2019
Southwest Airlines direct
return: Jul 23, 2019
Spirit Airlines direct
JetBlue
outbound: May 30, 2019
JetBlue direct
return: Jun 3, 2019
JetBlue direct
United Airlines
outbound: Jul 2, 2019
United Airlines direct
return: Jul 23, 2019
Spirit Airlines direct
American Airlines
outbound: Jul 5, 2019
American Airlines 1 stop
return: Jul 9, 2019
American Airlines direct
Delta Air Lines
outbound: Jun 25, 2019
Delta Air Lines 1 stop
return: Jun 27, 2019
Delta Air Lines 1 stop

Travel tips for flights Chicago - Boston

Average flight duration: 2h40m (direct flight)

  • Arrival city:
  • Boston, USA
  • Airport(s):
  • Logan International Airport (BOS)
  • Manchester–Boston Regional Airport (MHT)
  • Local time:
  • May 26, 2019 9:30 AM, GMT-4
  • Weather:
  • min. 59ºF, max. 79ºF
  • Departure city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • May 26, 2019 8:30 AM, GMT-5
  • Weather:
  • min. 41ºF, max. 58ºF