Boston to Chicago

BOSMDW

Fly from Boston to Chicago starting at USD 84 with Southwest Airlines.Best fare available on Jul 30, 2026.Limited seats. Better plans. Book before it's gone.

Boston to Chicago cheapest flights this week

7 Jul
Southwest Airlines
07:30BOS
10:10MDW
DirectUSD 176VIEW DEAL
7 Jul
Southwest Airlines
17:30BOS
20:25MDW
DirectUSD 152VIEW DEAL
10 Jul
Southwest Airlines
18:45BOS
21:35MDW
DirectUSD 135VIEW DEAL
10 Jul
Southwest Airlines
05:25BOS
08:00MDW
DirectUSD 139VIEW DEAL
15 Jul
Southwest Airlines
15:45BOS
18:30MDW
DirectUSD 98VIEW DEAL
15 Jul
Southwest Airlines
13:25BOS
16:05MDW
DirectUSD 140VIEW DEAL
16 Jul
Southwest Airlines
05:25BOS
08:00MDW
DirectUSD 110VIEW DEAL
17 Jul
Southwest Airlines
05:25BOS
08:00MDW
DirectUSD 110VIEW DEAL
18 Jul
Southwest Airlines
05:20BOS
07:55MDW
DirectUSD 103VIEW DEAL
30 Jul
Southwest Airlines
05:25BOS
08:00MDW
DirectUSD 84VIEW DEAL

Boston to Chicago monthly flight fare trend

Jul
from USD 84
Aug
from USD 79
Sep
from USD 109
Oct
No flights
Nov
from USD 98
Dec
from USD 137

Airport Details

Origin

Boston

Logan International Airport (BOS)

Boston, BOS
Zone

New York

Elev

20 ft

Destination

Chicago

Chicago Midway International Airport (MDW)

Chicago, MDW
Zone

Chicago

Elev

620 ft

Flights from Boston

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