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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  • price
  • month of departure
  • month of return
$113
Southwest Airlines outward: Jul 2, 2020
3:20a MDW » 5:35a BOS
Southwest Airlines direct (2h15m)
Spirit Airlines inbound: Jul 8, 2020
8:53p BOS » 11:48p ORD
Spirit Airlines direct (2h55m)
Return
Departure
Find the cheapest Chicago Boston flight by browsing the dates below to find alternative flight prices found in the last days. To launch a flight search for Chicago - Boston with these new dates, click on an offer. Want to depart from another city? Choose:

Airlines operating flights from Chicago to Boston

  • any
  • June 2020
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  • Alaska Airlines
  • JetBlue
JetBlue
outbound: Jul 1, 2020
JetBlue 2 stops
return: Jul 8, 2020
Spirit Airlines direct
Alaska Airlines
outbound: Jul 1, 2020
Alaska Airlines 1 stop
return: Jul 8, 2020
Spirit Airlines direct

Travel tips for flights Chicago - Boston

Average flight duration: 2h35m (direct flight)

  • Arrival city:
  • Boston, USA
  • Airport(s):
  • Logan International Airport (BOS)
  • Manchester–Boston Regional Airport (MHT)
  • Local time:
  • Jun 4, 2020 11:54 PM, GMT-4
  • Weather:
  • min. 67ºF, max. 82ºF
  • Departure city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Jun 4, 2020 10:54 PM, GMT-5
  • Weather:
  • min. 63ºF, max. 72ºF