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

Find cheap airline tickets from Boston to Chicago by date

  • any
  • October 2019
  • November 2019
  • December 2019
  • January 2020
  • February 2020
  • March 2020
  • April 2020
  • May 2020
  • June 2020
  • July 2020
  • August 2020
  • September 2020
  • any
  • October 2019
  • November 2019
  • December 2019
  • January 2020
  • February 2020
  • March 2020
  • April 2020
  • May 2020
  • June 2020
  • July 2020
  • August 2020
  • September 2020
  • price
  • month of departure
  • month of return
$120
Spirit Airlines outward: Oct 25, 2019
7:25p BOS » 10:20p ORD
Spirit Airlines direct (2h55m)
Spirit Airlines inbound: Oct 28, 2019
8:20p ORD » 10:48p BOS
Spirit Airlines direct (2h28m)
$127
Spirit Airlines outward: Oct 25, 2019
7:25p BOS » 10:20p ORD
Spirit Airlines direct (2h55m)
Spirit Airlines inbound: Oct 28, 2019
8:20p ORD » 10:48p BOS
Spirit Airlines direct (2h28m)
$131
Spirit Airlines outward: Oct 25, 2019
7:25p BOS » 10:20p ORD
Spirit Airlines direct (2h55m)
Spirit Airlines inbound: Oct 28, 2019
8:20p ORD » 10:48p BOS
Spirit Airlines direct (2h28m)
$137
United Airlines outward: Oct 25, 2019
11:20a BOS » 2:00p ORD
United Airlines direct (2h40m)
United Airlines inbound: Oct 29, 2019
3:30a ORD » 5:43a BOS
United Airlines direct (2h13m)
$161
Spirit Airlines outward: Nov 8, 2019
7:25p BOS » 10:20p ORD
Spirit Airlines direct (2h55m)
Spirit Airlines inbound: Nov 11, 2019
9:20p ORD » 11:48p BOS
Spirit Airlines direct (2h28m)
$163
United Airlines outward: Oct 25, 2019
11:20a BOS » 2:00p ORD
United Airlines direct (2h40m)
United Airlines inbound: Oct 29, 2019
3:30a ORD » 5:43a BOS
United Airlines direct (2h13m)
$213
United Airlines outward: Feb 13, 2020
2:31p BOS » 5:13p ORD
United Airlines direct (2h42m)
United Airlines inbound: Feb 19, 2020
4:05a ORD » 6:19a BOS
United Airlines direct (2h14m)
$214
United Airlines outward: Feb 13, 2020
4:20p BOS » 7:04p ORD
United Airlines direct (2h44m)
United Airlines inbound: Feb 18, 2020
1:00p ORD » 3:10p BOS
United Airlines direct (2h10m)
$295
JetBlue outward: Nov 29, 2019
4:55a BOS » 7:39a ORD
JetBlue direct (2h44m)
JetBlue inbound: Nov 30, 2019
12:01p ORD » 2:17p BOS
JetBlue direct (2h16m)
$296
JetBlue outward: Nov 29, 2019
4:55a BOS » 7:39a ORD
JetBlue direct (2h44m)
JetBlue inbound: Nov 30, 2019
12:01p ORD » 2:17p BOS
JetBlue direct (2h16m)
$296
JetBlue outward: Nov 29, 2019
4:55a BOS » 7:39a ORD
JetBlue direct (2h44m)
JetBlue inbound: Nov 30, 2019
12:01p ORD » 2:17p BOS
JetBlue direct (2h16m)
$296
JetBlue outward: Nov 29, 2019
4:55a BOS » 7:39a ORD
JetBlue direct (2h44m)
JetBlue inbound: Nov 30, 2019
12:01p ORD » 2:17p BOS
JetBlue direct (2h16m)
$310
JetBlue outward: Nov 29, 2019
4:55a BOS » 7:39a ORD
JetBlue direct (2h44m)
Spirit Airlines inbound: Dec 2, 2019
3:45a ORD » 1:29p BOS
Spirit Airlines 1 stop (9h44m)
$357
Spirit Airlines outward: Nov 29, 2019
4:29a BOS » 2:17p ORD
Spirit Airlines 1 stop (9h48m)
Spirit Airlines inbound: Nov 30, 2019
10:56p ORD » 11:48a BOS
Spirit Airlines 1 stop (12h52m)
Return
Departure
Choose when you'd like to depart to Chicago (USA):
Find the cheapest Boston Chicago flight by browsing the dates below to find alternative flight prices found in the last days. To launch a flight search for Boston - Chicago with these new dates, click on an offer. Want to depart from another city? Choose:

Airlines operating flights from Boston to Chicago

  • any
  • October 2019
  • November 2019
  • December 2019
  • January 2020
  • February 2020
  • March 2020
  • April 2020
  • May 2020
  • June 2020
  • July 2020
  • August 2020
  • September 2020
  • all
  • JetBlue
  • Spirit Airlines
Spirit Airlines
outbound: Oct 30, 2019
Spirit Airlines direct
return: Nov 3, 2019
Spirit Airlines direct
JetBlue
outbound: Nov 28, 2019
JetBlue direct
return: Nov 30, 2019
JetBlue direct

Travel tips for flights Boston - Chicago

Average flight duration: 2h34m (direct flight)

  • Arrival city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Oct 15, 2019 1:32 AM, GMT-5
  • Weather:
  • min. 48ºF, max. 54ºF
  • Departure city:
  • Boston, USA
  • Airport(s):
  • Logan International Airport (BOS)
  • Manchester–Boston Regional Airport (MHT)
  • Local time:
  • Oct 15, 2019 2:32 AM, GMT-4
  • Weather:
  • min. 49ºF, max. 62ºF