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

Find cheap airline tickets from Boston to Chicago by date

  • any
  • August 2020
  • September 2020
  • October 2020
  • November 2020
  • December 2020
  • January 2021
  • February 2021
  • March 2021
  • April 2021
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  • any
  • August 2020
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  • price
  • month of departure
  • month of return
$43
Spirit Airlines outward: Aug 21, 2020
1:00p BOS » 3:57p ORD
Spirit Airlines direct (2h57m)
Spirit Airlines inbound: Aug 25, 2020
1:40a ORD » 4:05a BOS
Spirit Airlines direct (2h25m)
$69
JetBlue outward: Sep 9, 2020
2:30p BOS » 5:20p ORD
JetBlue direct (2h50m)
JetBlue inbound: Sep 24, 2020
1:30a ORD » 3:45a BOS
JetBlue direct (2h15m)
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
  • August 2020
  • September 2020
  • October 2020
  • November 2020
  • December 2020
  • January 2021
  • February 2021
  • March 2021
  • April 2021
  • May 2021
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  • all
  • Alaska Airlines
  • American Airlines
  • Spirit Airlines
Spirit Airlines
outbound: Aug 21, 2020
Spirit Airlines direct
return: Aug 24, 2020
Spirit Airlines direct
American Airlines
outbound: Sep 9, 2020
American Airlines direct
return: Sep 23, 2020
American Airlines direct
Alaska Airlines
outbound: Sep 9, 2020
Alaska Airlines 1 stop
return: Sep 23, 2020
Alaska Airlines 1 stop

Travel tips for flights Boston - Chicago

Average flight duration: 2h41m (direct flight)

  • Arrival city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Aug 13, 2020 11:36 PM, GMT-5
  • Weather:
  • min. 74ºF, max. 83ºF
  • Departure city:
  • Boston, USA
  • Airport(s):
  • Logan International Airport (BOS)
  • Manchester–Boston Regional Airport (MHT)
  • Local time:
  • Aug 14, 2020 12:36 AM, GMT-4
  • Weather:
  • min. 63ºF, max. 73ºF