Boston to Chicago

BOSMDW

Fly from Boston to Chicago starting at USD 101 with Southwest Airlines.Best fare available on Jul 25, 2026.Limited seats. Better plans. Book before it's gone.

Boston to Chicago cheapest flights this week

19 Jul
Southwest Airlines
22:05BOS
00:50MDW
DirectUSD 169VIEW DEAL
19 Jul
Southwest Airlines
05:50BOS
11:10MDW
1 StopUSD 188VIEW DEAL
23 Jul
Southwest Airlines
05:25BOS
08:00MDW
DirectUSD 139VIEW DEAL
25 Jul
Southwest Airlines
05:20BOS
07:55MDW
DirectUSD 101VIEW DEAL
27 Jul
Southwest Airlines
05:25BOS
08:00MDW
DirectUSD 144VIEW DEAL
28 Jul
Southwest Airlines
05:35BOS
08:10MDW
DirectUSD 114VIEW DEAL
30 Jul
Southwest Airlines
05:25BOS
08:00MDW
DirectUSD 140VIEW DEAL
30 Jul
Frontier Airlines
11:52BOS
23:03MDW
1 StopUSD 136VIEW DEAL
31 Jul
Frontier Airlines
06:00BOS
12:09MDW
1 StopUSD 147VIEW DEAL
1 Aug
Southwest Airlines
05:20BOS
07:55MDW
DirectUSD 123VIEW DEAL

Boston to Chicago monthly flight fare trend

Jul
from USD 101
Aug
from USD 76
Sep
from USD 77
Oct
from USD 76
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

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