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

Find cheap airline tickets from Boston to Chicago by date

  • any
  • February 2020
  • March 2020
  • April 2020
  • May 2020
  • June 2020
  • July 2020
  • August 2020
  • September 2020
  • October 2020
  • November 2020
  • December 2020
  • January 2021
  • any
  • February 2020
  • March 2020
  • April 2020
  • May 2020
  • June 2020
  • July 2020
  • August 2020
  • September 2020
  • October 2020
  • November 2020
  • December 2020
  • January 2021
  • price
  • month of departure
  • month of return
$112
JetBlue outward: Feb 26, 2020
8:26p BOS » 11:28p ORD
JetBlue direct (3h02m)
JetBlue inbound: Mar 11, 2020
3:05p ORD » 5:25p BOS
JetBlue direct (2h20m)
$112
JetBlue outward: Feb 27, 2020
12:39p BOS » 3:41p ORD
JetBlue direct (3h02m)
JetBlue inbound: Mar 5, 2020
12:57p ORD » 3:12p BOS
JetBlue direct (2h15m)
$135
Delta Air Lines outward: Mar 2, 2020
6:10p BOS » 9:15p ORD
Delta Air Lines direct (3h05m)
JetBlue inbound: Mar 9, 2020
12:00p ORD » 2:23p BOS
JetBlue direct (2h23m)
$139
Southwest Airlines outward: Apr 16, 2020
11:30a BOS » 2:10p MDW
Southwest Airlines direct (2h40m)
Southwest Airlines inbound: Apr 23, 2020
1:05p MDW » 3:20p BOS
Southwest Airlines direct (2h15m)
$140
JetBlue outward: Mar 19, 2020
1:27p BOS » 4:31p ORD
JetBlue direct (3h04m)
JetBlue inbound: Mar 26, 2020
12:00p ORD » 2:23p BOS
JetBlue direct (2h23m)
$145
Spirit Airlines outward: May 11, 2020
9:23p BOS » 12:07a ORD
Spirit Airlines direct (2h44m)
Spirit Airlines inbound: May 19, 2020
4:49a ORD » 4:52p BOS
Spirit Airlines 1 stop (12h03m)
$149
JetBlue outward: Jun 13, 2020
12:28p BOS » 3:23p ORD
JetBlue direct (2h55m)
JetBlue inbound: Aug 9, 2020
4:24a ORD » 6:50a BOS
JetBlue direct (2h26m)
$154
JetBlue outward: Mar 19, 2020
11:28a BOS » 2:30p ORD
JetBlue direct (3h02m)
JetBlue inbound: Mar 30, 2020
1:00p ORD » 3:23p BOS
JetBlue direct (2h23m)
$154
JetBlue outward: Mar 19, 2020
11:28a BOS » 2:30p ORD
JetBlue direct (3h02m)
JetBlue inbound: Mar 30, 2020
1:00p ORD » 3:23p BOS
JetBlue direct (2h23m)
$163
American Airlines outward: Feb 27, 2020
5:00p BOS » 8:09p ORD
American Airlines direct (3h09m)
American Airlines inbound: Feb 28, 2020
10:45p ORD » 4:58a BOS
American Airlines 1 stop (6h13m)
$167
Delta Air Lines outward: Sep 8, 2020
12:00p BOS » 3:03p ORD
Delta Air Lines direct (3h03m)
Delta Air Lines inbound: Sep 15, 2020
1:00p ORD » 3:35p BOS
Delta Air Lines direct (2h35m)
$180
United Airlines outward: Jul 1, 2020
1:02p BOS » 4:02p ORD
United Airlines direct (3h)
United Airlines inbound: Jul 9, 2020
4:05a ORD » 6:19a BOS
United Airlines direct (2h14m)
$199
Southwest Airlines outward: Jul 13, 2020
11:30a BOS » 2:10p MDW
Southwest Airlines direct (2h40m)
United Airlines inbound: Jul 16, 2020
4:05a ORD » 6:19a BOS
United Airlines direct (2h14m)
$232
JetBlue outward: Mar 10, 2020
12:56a BOS » 3:53a ORD
JetBlue direct (2h57m)
JetBlue inbound: Mar 14, 2020
12:00p ORD » 2:23p BOS
JetBlue direct (2h23m)
$263
JetBlue outward: Mar 15, 2020
11:28a BOS » 2:30p ORD
JetBlue direct (3h02m)
JetBlue inbound: Mar 22, 2020
12:00p ORD » 2:23p BOS
JetBlue direct (2h23m)
$306
JetBlue outward: Jun 18, 2020
12:28p BOS » 3:25p ORD
JetBlue direct (2h57m)
Sun Country inbound: Jun 22, 2020
12:20a ORD » 4:33p BOS
Sun Country 1 stop (16h13m)
$325
Delta Air Lines outward: Mar 13, 2020
11:10a BOS » 2:18p ORD
Delta Air Lines direct (3h08m)
Southwest Airlines inbound: Mar 22, 2020
1:25p MDW » 3:40p BOS
Southwest Airlines direct (2h15m)
$344
JetBlue outward: Jul 1, 2020
12:28p BOS » 3:23p ORD
JetBlue direct (2h55m)
JetBlue inbound: Jul 11, 2020
3:58p ORD » 6:24p BOS
JetBlue direct (2h26m)
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
  • February 2020
  • March 2020
  • April 2020
  • May 2020
  • June 2020
  • July 2020
  • August 2020
  • September 2020
  • October 2020
  • November 2020
  • December 2020
  • January 2021
  • all
  • JetBlue
  • Spirit Airlines
JetBlue
outbound: Mar 2, 2020
JetBlue direct
return: Mar 9, 2020
JetBlue direct
Spirit Airlines
outbound: May 11, 2020
Spirit Airlines direct
return: May 18, 2020
Spirit Airlines 1 stop

Travel tips for flights Boston - Chicago

Average flight duration: 2h42m (direct flight)

  • Arrival city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Feb 25, 2020 4:48 PM, GMT-6
  • Weather:
  • min. 29ºF, max. 33ºF
  • Departure city:
  • Boston, USA
  • Airport(s):
  • Logan International Airport (BOS)
  • Manchester–Boston Regional Airport (MHT)
  • Local time:
  • Feb 25, 2020 5:48 PM, GMT-5
  • Weather:
  • min. 35ºF, max. 46ºF