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

Find cheap airline tickets from Chicago to Boston by date

  • any
  • December 2021
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  • July 2022
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  • any
  • December 2021
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  • price
  • month of departure
  • month of return
$151
American Airlines outward: Jan 13, 2022
3:10p ORD » 5:25p BOS
American Airlines direct (2h15m)
American Airlines inbound: Jan 17, 2022
12:40p BOS » 9:29p ORD
American Airlines 1 stop (8h49m)
$151
American Airlines outward: Jan 20, 2022
9:24p ORD » 2:42a BOS
American Airlines 1 stop (5h18m)
American Airlines inbound: Jan 23, 2022
11:00a BOS » 2:07p ORD
American Airlines direct (3h07m)
$152
American Airlines outward: Jan 21, 2022
7:06p ORD » 10:47p BOS
American Airlines 1 stop (3h41m)
American Airlines inbound: Jan 23, 2022
11:00a BOS » 2:07p ORD
American Airlines direct (3h07m)
$153
United Airlines outward: Jan 21, 2022
2:45p ORD » 5:03p BOS
United Airlines direct (2h18m)
United Airlines inbound: Jan 23, 2022
1:45p BOS » 6:55p ORD
United Airlines 1 stop (5h10m)
Return
Departure
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Airlines operating flights from Chicago to Boston

  • any
  • December 2021
  • January 2022
  • February 2022
  • March 2022
  • April 2022
  • May 2022
  • June 2022
  • July 2022
  • August 2022
  • September 2022
  • October 2022
  • November 2022
  • all
  • Alaska Airlines
  • JetBlue
  • Spirit Airlines
  • United Airlines
JetBlue
outbound: Jan 21, 2022
JetBlue direct
return: Jan 23, 2022
JetBlue direct
Spirit Airlines
outbound: Jan 21, 2022
Spirit Airlines 1 stop
return: Jan 23, 2022
Spirit Airlines 1 stop
United Airlines
outbound: Jan 21, 2022
United Airlines direct
return: Jan 23, 2022
United Airlines 1 stop
Alaska Airlines
outbound: Jan 21, 2022
Alaska Airlines 1 stop
return: Jan 23, 2022
Alaska Airlines 1 stop

Travel tips for flights Chicago - Boston

Average flight duration: 2h42m (direct flight)

  • Arrival city:
  • Boston, USA
  • Airport(s):
  • Logan International Airport (BOS)
  • Manchester–Boston Regional Airport (MHT)
  • Local time:
  • Dec 8, 2021 2:07 PM, GMT-5
  • Weather:
  • min. 33ºF, max. 40ºF
  • Departure city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Dec 8, 2021 1:07 PM, GMT-6
  • Weather:
  • min. 29ºF, max. 39ºF