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

Find cheap airline tickets from Chicago to Boston by date

  • any
  • April 2020
  • May 2020
  • June 2020
  • July 2020
  • August 2020
  • September 2020
  • October 2020
  • November 2020
  • December 2020
  • January 2021
  • February 2021
  • March 2021
  • any
  • April 2020
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  • price
  • month of departure
  • month of return
$67
Spirit Airlines outward: May 30, 2020
10:51p ORD » 1:21a BOS
Spirit Airlines direct (2h30m)
Delta Air Lines inbound: Jun 8, 2020
1:59a BOS » 4:57a ORD
Delta Air Lines direct (2h58m)
$89
United Airlines outward: Jul 22, 2020
1:00p ORD » 3:19p BOS
United Airlines direct (2h19m)
American Airlines inbound: Jul 26, 2020
3:11a BOS » 6:03a ORD
American Airlines direct (2h52m)
$128
American Airlines outward: Jul 25, 2020
3:45p ORD » 10:14p BOS
American Airlines 1 stop (6h29m)
American Airlines inbound: Jul 30, 2020
12:00p BOS » 2:41p ORD
American Airlines direct (2h41m)
$137
United Airlines outward: Aug 5, 2020
1:00p ORD » 3:19p BOS
United Airlines direct (2h19m)
American Airlines inbound: Aug 9, 2020
12:30p BOS » 5:18p ORD
American Airlines 1 stop (4h48m)
$191
JetBlue outward: Jul 24, 2020
4:24a ORD » 6:49a BOS
JetBlue direct (2h25m)
JetBlue inbound: Jul 27, 2020
6:47p BOS » 1:32a ORD
JetBlue 1 stop (6h45m)
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
  • April 2020
  • May 2020
  • June 2020
  • July 2020
  • August 2020
  • September 2020
  • October 2020
  • November 2020
  • December 2020
  • January 2021
  • February 2021
  • March 2021
  • all
  • JetBlue
  • Spirit Airlines
  • United Airlines
Spirit Airlines
outbound: May 30, 2020
Spirit Airlines direct
return: Jun 7, 2020
Delta Air Lines direct
JetBlue
outbound: May 30, 2020
JetBlue direct
return: Jun 7, 2020
JetBlue 1 stop
United Airlines
outbound: Jul 22, 2020
United Airlines direct
return: Jul 25, 2020
American Airlines direct

Travel tips for flights Chicago - Boston

Average flight duration: 2h34m (direct flight)

  • Arrival city:
  • Boston, USA
  • Airport(s):
  • Logan International Airport (BOS)
  • Manchester–Boston Regional Airport (MHT)
  • Local time:
  • Apr 1, 2020 8:37 PM, GMT-4
  • Weather:
  • min. 38ºF, max. 45ºF
  • Departure city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Apr 1, 2020 7:37 PM, GMT-5
  • Weather:
  • min. 43ºF, max. 55ºF