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Find cheap airline tickets from Chicago to Boston by date

Departure: Return: Sorted by:

$301

outward: Jun 25, 2023
3:58p MDW » 7:54p BOS
Unknown Company 1 stop (27h56m)

inbound: Jul 24, 2023
9:48p BOS » 4:40p MDW
Unknown Company 1 stop (18h52m)

$313

outward: Jun 2, 2023
5:31p MDW » 3:47p BOS
Allegiant Air 1 stop (22h16m)

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

Departure: Airline

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

Airline tickets Chicago - Boston found in the last 30 days.

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

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