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

Find cheap airline tickets from Boston to Chicago by date

  • any
  • December 2019
  • January 2020
  • February 2020
  • March 2020
  • April 2020
  • May 2020
  • June 2020
  • July 2020
  • August 2020
  • September 2020
  • October 2020
  • November 2020
  • any
  • December 2019
  • January 2020
  • February 2020
  • March 2020
  • April 2020
  • May 2020
  • June 2020
  • July 2020
  • August 2020
  • September 2020
  • October 2020
  • November 2020
  • price
  • month of departure
  • month of return
$181
JetBlue outward: Dec 31, 2019
12:46p BOS » 3:47p ORD
JetBlue direct (3h01m)
JetBlue inbound: Jan 6, 2020
4:38a ORD » 6:50a BOS
JetBlue direct (2h12m)
$187
American Airlines outward: Feb 13, 2020
11:00a BOS » 1:41p ORD
American Airlines direct (2h41m)
United Airlines inbound: Feb 18, 2020
1:00p ORD » 3:12p BOS
United Airlines direct (2h12m)
$187
American Airlines outward: Feb 13, 2020
11:00a BOS » 1:41p ORD
American Airlines direct (2h41m)
United Airlines inbound: Feb 18, 2020
1:00p ORD » 3:12p BOS
United Airlines direct (2h12m)
$199
American Airlines outward: Feb 13, 2020
12:00p BOS » 2:41p ORD
American Airlines direct (2h41m)
American Airlines inbound: Feb 18, 2020
7:35p ORD » 12:31a BOS
American Airlines 1 stop (4h56m)
$204
JetBlue outward: Feb 13, 2020
1:00p BOS » 4:05p ORD
JetBlue direct (3h05m)
JetBlue inbound: Feb 19, 2020
12:40a ORD » 3:02a BOS
JetBlue direct (2h22m)
$221
United Airlines outward: Dec 24, 2019
2:03a BOS » 4:57a ORD
United Airlines direct (2h54m)
JetBlue inbound: Jan 3, 2020
4:38a ORD » 6:50a BOS
JetBlue direct (2h12m)
$228
Southwest Airlines outward: Apr 13, 2020
11:20a BOS » 2:05p MDW
Southwest Airlines direct (2h45m)
American Airlines inbound: Apr 16, 2020
1:00p ORD » 3:16p BOS
American Airlines direct (2h16m)
$228
Southwest Airlines outward: Apr 13, 2020
11:20a BOS » 2:05p MDW
Southwest Airlines direct (2h45m)
American Airlines inbound: Apr 16, 2020
1:00p ORD » 3:16p BOS
American Airlines direct (2h16m)
$292
United Airlines outward: Apr 16, 2020
7:00p BOS » 9:44p ORD
United Airlines direct (2h44m)
United Airlines inbound: Apr 21, 2020
12:57a ORD » 3:11a BOS
United Airlines direct (2h14m)
$292
United Airlines outward: Apr 16, 2020
7:00p BOS » 9:44p ORD
United Airlines direct (2h44m)
United Airlines inbound: Apr 21, 2020
12:57a ORD » 3:11a BOS
United Airlines direct (2h14m)
$473
Delta Air Lines outward: Jan 15, 2020
12:10p BOS » 3:23p ORD
Delta Air Lines direct (3h13m)
Delta Air Lines inbound: Jan 19, 2020
12:20p ORD » 4:33p BOS
Delta Air Lines 1 stop (4h13m)
$489
Delta Air Lines outward: May 20, 2020
2:55p BOS » 5:52p ORD
Delta Air Lines direct (2h57m)
Delta Air Lines inbound: May 27, 2020
1:00p ORD » 3:22p BOS
Delta Air Lines direct (2h22m)
$798
Delta Air Lines outward: Apr 19, 2020
7:00p BOS » 3:05a ORD
Delta Air Lines 1 stop (8h05m)
Delta Air Lines inbound: Apr 26, 2020
3:44p ORD » 6:08p BOS
Delta Air Lines direct (2h24m)
Return
Departure
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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
  • December 2019
  • January 2020
  • February 2020
  • March 2020
  • April 2020
  • May 2020
  • June 2020
  • July 2020
  • August 2020
  • September 2020
  • October 2020
  • November 2020
  • all
  • JetBlue
  • Spirit Airlines
  • United Airlines
Spirit Airlines
outbound: Dec 23, 2019
Spirit Airlines 1 stop
return: Jan 2, 2020
JetBlue direct
JetBlue
outbound: Dec 23, 2019
JetBlue direct
return: Jan 2, 2020
JetBlue direct
United Airlines
outbound: Dec 23, 2019
United Airlines direct
return: Jan 2, 2020
JetBlue direct

Travel tips for flights Boston - Chicago

Average flight duration: 2h35m (direct flight)

  • Arrival city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Dec 5, 2019 11:17 AM, GMT-6
  • Weather:
  • min. 28ºF, max. 39ºF
  • Departure city:
  • Boston, USA
  • Airport(s):
  • Logan International Airport (BOS)
  • Manchester–Boston Regional Airport (MHT)
  • Local time:
  • Dec 5, 2019 12:17 PM, GMT-5
  • Weather:
  • min. 28ºF, max. 37ºF