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 2019
  • September 2019
  • October 2019
  • November 2019
  • December 2019
  • January 2020
  • February 2020
  • March 2020
  • April 2020
  • May 2020
  • June 2020
  • July 2020
  • any
  • August 2019
  • September 2019
  • October 2019
  • November 2019
  • December 2019
  • January 2020
  • February 2020
  • March 2020
  • April 2020
  • May 2020
  • June 2020
  • July 2020
  • price
  • month of departure
  • month of return
$139
Spirit Airlines outward: Oct 4, 2019
7:25p BOS » 10:22p ORD
Spirit Airlines direct (2h57m)
Spirit Airlines inbound: Oct 11, 2019
9:15p ORD » 11:49p BOS
Spirit Airlines direct (2h34m)
$193
United Airlines outward: Feb 13, 2020
1:02p BOS » 4:02p ORD
United Airlines direct (3h)
United Airlines inbound: Feb 18, 2020
2:45p ORD » 5:06p BOS
United Airlines direct (2h21m)
$195
United Airlines outward: Feb 13, 2020
2:31p BOS » 5:13p ORD
United Airlines direct (2h42m)
United Airlines inbound: Feb 18, 2020
1:00p ORD » 3:10p BOS
United Airlines direct (2h10m)
$195
United Airlines outward: Feb 13, 2020
2:31p BOS » 5:13p ORD
United Airlines direct (2h42m)
United Airlines inbound: Feb 19, 2020
4:05a ORD » 6:19a BOS
United Airlines direct (2h14m)
Return
Departure
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 2019
  • September 2019
  • October 2019
  • November 2019
  • December 2019
  • January 2020
  • February 2020
  • March 2020
  • April 2020
  • May 2020
  • June 2020
  • July 2020
  • all
  • Spirit Airlines
Spirit Airlines
outbound: Oct 4, 2019
Spirit Airlines direct
return: Oct 11, 2019
Spirit Airlines direct

Travel tips for flights Boston - Chicago

Average flight duration: 2h34m (direct flight)

  • Arrival city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Aug 22, 2019 8:38 AM, GMT-5
  • Weather:
  • min. 68ºF, max. 72ºF
  • Departure city:
  • Boston, USA
  • Airport(s):
  • Logan International Airport (BOS)
  • Manchester–Boston Regional Airport (MHT)
  • Local time:
  • Aug 22, 2019 9:38 AM, GMT-4
  • Weather:
  • min. 70ºF, max. 86ºF