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 2021
  • March 2021
  • April 2021
  • May 2021
  • June 2021
  • July 2021
  • August 2021
  • September 2021
  • October 2021
  • November 2021
  • December 2021
  • January 2022
  • any
  • February 2021
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  • price
  • month of departure
  • month of return
$68
Spirit Airlines outward: May 10, 2021
6:47p BOS » 9:37p ORD
Spirit Airlines direct (2h50m)
Spirit Airlines inbound: May 23, 2021
10:22p ORD » 12:45a BOS
Spirit Airlines direct (2h23m)
$81
United Airlines outward: Mar 16, 2021
11:00a BOS » 2:02p ORD
United Airlines direct (3h02m)
United Airlines inbound: Mar 20, 2021
4:45p ORD » 7:02p BOS
United Airlines direct (2h17m)
$82
American Airlines outward: Mar 22, 2021
8:45p BOS » 11:43p ORD
American Airlines direct (2h58m)
American Airlines inbound: Mar 28, 2021
1:00a ORD » 4:28a BOS
American Airlines direct (2h28m)
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 2021
  • March 2021
  • April 2021
  • May 2021
  • June 2021
  • July 2021
  • August 2021
  • September 2021
  • October 2021
  • November 2021
  • December 2021
  • January 2022
  • all
  • Alaska Airlines
  • American Airlines
  • Spirit Airlines
  • United Airlines
Spirit Airlines
outbound: May 10, 2021
Spirit Airlines direct
return: May 23, 2021
Spirit Airlines direct
United Airlines
outbound: Mar 16, 2021
United Airlines direct
return: Mar 20, 2021
United Airlines direct
American Airlines
outbound: Mar 22, 2021
American Airlines direct
return: Mar 27, 2021
American Airlines direct
Alaska Airlines
outbound: Mar 16, 2021
Alaska Airlines 1 stop
return: Mar 20, 2021
Alaska Airlines 1 stop

Travel tips for flights Boston - Chicago

Average flight duration: 2h39m (direct flight)

  • Arrival city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Feb 28, 2021 4:24 PM, GMT-6
  • Weather:
  • min. 30ºF, max. 39ºF
  • Departure city:
  • Boston, USA
  • Airport(s):
  • Logan International Airport (BOS)
  • Manchester–Boston Regional Airport (MHT)
  • Local time:
  • Feb 28, 2021 5:24 PM, GMT-5
  • Weather:
  • min. 33ºF, max. 44ºF