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

Find cheap airline tickets from Chicago to Boston by date

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$490
United Airlines outward: Nov 20, 2022
1:28a ORD » 3:49a BOS
United Airlines direct (2h21m)
United Airlines inbound: Nov 28, 2022
2:17a BOS » 5:07a ORD
United Airlines direct (2h50m)
$537
United Airlines outward: Nov 18, 2022
7:12p ORD » 11:58p BOS
United Airlines 1 stop (4h46m)
United Airlines inbound: Nov 28, 2022
2:17a BOS » 5:07a ORD
United Airlines direct (2h50m)
Return
Departure
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Airlines operating flights from Chicago to Boston

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  • October 2022
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  • Spirit Airlines
  • United Airlines
Spirit Airlines
outbound: Nov 19, 2022
Spirit Airlines 1 stop
return: Nov 27, 2022
Spirit Airlines 1 stop
United Airlines
outbound: Nov 19, 2022
United Airlines direct
return: Nov 27, 2022
United Airlines direct

Travel tips for flights Chicago - Boston

Average flight duration: 2h40m (direct flight)

  • Arrival city:
  • Boston, USA
  • Airport(s):
  • Boston Logan International Airport (BOS)
  • Manchester–Boston Regional Airport (MHT)
  • Local time:
  • Oct 2, 2022 3:28 PM, GMT-4
  • Weather:
  • min. 47ºF, max. 59ºF
  • Departure city:
  • Chicago, USA
  • Airport(s):
  • Chicago Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Oct 2, 2022 2:28 PM, GMT-5
  • Weather:
  • min. 52ºF, max. 68ºF