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

Find cheap airline tickets from Boston to Chicago by date

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  • May 2021
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  • any
  • May 2021
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  • price
  • month of departure
  • month of return
$138
Frontier Airlines outward: May 18, 2021
5:29p BOS » 5:28a ORD
Frontier Airlines 1 stop (11h59m)
Spirit Airlines inbound: May 25, 2021
4:09p ORD » 12:29a BOS
Spirit Airlines 1 stop (8h20m)
$188
Spirit Airlines outward: May 20, 2021
11:20a BOS » 2:34a ORD
Spirit Airlines 1 stop (15h14m)
Spirit Airlines inbound: May 27, 2021
7:40p ORD » 12:29a BOS
Spirit Airlines 1 stop (4h49m)
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
  • May 2021
  • June 2021
  • July 2021
  • August 2021
  • September 2021
  • October 2021
  • November 2021
  • December 2021
  • January 2022
  • February 2022
  • March 2022
  • April 2022
  • all
  • American Airlines
  • Frontier Airlines
  • Spirit Airlines
Spirit Airlines
outbound: May 18, 2021
Spirit Airlines 1 stop
return: May 25, 2021
Spirit Airlines 1 stop
Frontier Airlines
outbound: May 18, 2021
Frontier Airlines 1 stop
return: May 25, 2021
Spirit Airlines 1 stop
American Airlines
outbound: May 18, 2021
American Airlines 1 stop
return: May 25, 2021
American Airlines 1 stop

Travel tips for flights Boston - Chicago

Average flight duration: 10h05m (flight with stopovers)

  • Arrival city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • May 16, 2021 4:37 PM, GMT-5
  • Weather:
  • min. 53ºF, max. 61ºF
  • Departure city:
  • Boston, USA
  • Airport(s):
  • Logan International Airport (BOS)
  • Manchester–Boston Regional Airport (MHT)
  • Local time:
  • May 16, 2021 5:37 PM, GMT-4
  • Weather:
  • min. 54ºF, max. 70ºF