Boston to Chicago

BOSMDW

Fly from Boston to Chicago starting at USD 96 with Southwest Airlines.Best fare available on Oct 6, 2026.Limited seats. Better plans. Book before it's gone.

Boston to Chicago cheapest flights this week

1 Oct
Southwest Airlines
13:10BOS
15:45MDW
DirectUSD 115VIEW DEAL
1 Oct
Frontier Airlines
12:54BOS
00:44MDW
1 StopUSD 162VIEW DEAL
1 Oct
Southwest Airlines
22:00BOS
00:35MDW
DirectUSD 154VIEW DEAL
2 Oct
Frontier Airlines
12:54BOS
18:51MDW
1 StopUSD 141VIEW DEAL
3 Oct
Frontier Airlines
12:54BOS
18:51MDW
1 StopUSD 157VIEW DEAL
4 Oct
Southwest Airlines
22:50BOS
01:30MDW
DirectUSD 254VIEW DEAL
4 Oct
Southwest Airlines
06:10BOS
08:45MDW
DirectUSD 291VIEW DEAL
5 Oct
Southwest Airlines
22:00BOS
00:40MDW
DirectUSD 199VIEW DEAL
5 Oct
Southwest Airlines
05:50BOS
08:25MDW
DirectUSD 114VIEW DEAL
6 Oct
Southwest Airlines
16:20BOS
18:55MDW
DirectUSD 96VIEW DEAL

Boston to Chicago monthly flight fare trend

Oct
from USD 77
Nov
from USD 95
Dec
from USD 113
Jan
from USD 141
Feb
No flights
Mar
from USD 191

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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