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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$301
Unknown Company outward: Jun 25, 2023
3:58p MDW » 7:54p BOS
Unknown Company 1 stop (27h56m)
Unknown Company inbound: Jul 24, 2023
9:48p BOS » 4:40p MDW
Unknown Company 1 stop (18h52m)
$313
Allegiant Air outward: Jun 2, 2023
5:31p MDW » 3:47p BOS
Allegiant Air 1 stop (22h16m)
Unknown Company inbound: Jun 4, 2023
4:00p BOS » 4:41p RFD
Unknown Company 1 stop (24h41m)
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
  • May 2023
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  • all
  • Allegiant Air
  • American Airlines
  • Spirit Airlines
  • United Airlines
Allegiant Air
outbound: Jun 25, 2023
Allegiant Air 1 stop
return: Jul 24, 2023
JetBlue 1 stop
Spirit Airlines
outbound: Jun 2, 2023
Spirit Airlines 1 stop
return: Jun 4, 2023
United Airlines direct
United Airlines
outbound: Jun 2, 2023
United Airlines direct
return: Jun 4, 2023
United Airlines direct
American Airlines
outbound: Jun 2, 2023
American Airlines direct
return: Jun 4, 2023
American Airlines direct

Travel tips for flights Chicago - Boston

Average flight duration: 23h28m (flight with stopovers)

  • Arrival city:
  • Boston, USA
  • Airport(s):
  • Boston Logan International Airport (BOS)
  • Manchester–Boston Regional Airport (MHT)
  • Local time:
  • May 29, 2023 1:43 AM, GMT-4
  • Weather:
  • min. 50ºF, max. 70ºF
  • Departure city:
  • Chicago, USA
  • Airport(s):
  • Chicago Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • May 29, 2023 12:43 AM, GMT-5
  • Weather:
  • min. 57ºF, max. 74ºF