Find cheap airline tickets from Boston to Chicago by date

Departure: Return: Sorted by:

$138

outward: May 18, 2021
5:29p BOS » 5:28a ORD
Frontier Airlines 1 stop (11h59m)

inbound: May 25, 2021
4:09p ORD » 12:29a BOS
Spirit Airlines 1 stop (8h20m)

Verify

$188

outward: May 20, 2021
11:20a BOS » 2:34a ORD
Spirit Airlines 1 stop (15h14m)

inbound: May 27, 2021
7:40p ORD » 12:29a BOS
Spirit Airlines 1 stop (4h49m)

Verify

Return

Departure

Choose when you'd like to depart to Chicago (USA):

Find the cheapest Boston Chicago flight by browsing the dates below to find alternative flight prices found in the last days. To launch a flight search for Boston - Chicago with these new dates, click on an offer. Want to depart from another city? Choose:

Airlines operating flights from Boston to Chicago

Departure: Airline

Spirit Airlines

outbound: May 18, 2021
Spirit Airlines 1 stop

return: May 25, 2021
Spirit Airlines 1 stop

$182 Verify

Frontier Airlines

outbound: May 18, 2021
Frontier Airlines 1 stop

return: May 25, 2021
Spirit Airlines 1 stop

$145 Verify

American Airlines

outbound: May 18, 2021
American Airlines 1 stop

return: May 25, 2021
American Airlines 1 stop

$249 Verify

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

Travel tips for flights Boston - Chicago

Average flight duration: 10h05m (flight with stopovers)

Arrival city:
Chicago, USA
Airport(s):
Midway International Airport (MDW)
O'Hare International Airport (ORD)
Local time:
May 16, 2021 4:37 PM, GMT-5
Weather:
min. 53ºF, max. 61ºF

Departure city:
Boston, USA
Airport(s):
Logan International Airport (BOS)
Manchester–Boston Regional Airport (MHT)
Local time:
May 16, 2021 5:37 PM, GMT-4
Weather:
min. 54ºF, max. 70ºF

Find a cheap rental car in Chicago