Boston to Chicago

BOSMDW

Fly from Boston to Chicago starting at SAR 403 with Southwest Airlines.Best fare available on Aug 19, 2026.Limited seats. Better plans. Book before it's gone.

Boston to Chicago cheapest flights this week

14 Aug
Southwest Airlines
18:40BOS
21:20MDW
DirectSAR 414VIEW DEAL
14 Aug
Southwest Airlines
20:20BOS
23:00MDW
DirectSAR 581VIEW DEAL
15 Aug
Frontier Airlines
12:56BOS
23:03MDW
1 StopSAR 681VIEW DEAL
15 Aug
Southwest Airlines
05:00BOS
14:20MDW
1 StopSAR 729VIEW DEAL
16 Aug
Southwest Airlines
21:05BOS
23:40MDW
DirectSAR 585VIEW DEAL
16 Aug
Southwest Airlines
07:30BOS
10:05MDW
DirectSAR 696VIEW DEAL
16 Aug
Southwest Airlines
07:30BOS
10:05MDW
DirectSAR 666VIEW DEAL
18 Aug
Southwest Airlines
10:05BOS
12:35MDW
DirectSAR 418VIEW DEAL
19 Aug
Southwest Airlines
07:30BOS
10:05MDW
DirectSAR 403VIEW DEAL
19 Aug
Frontier Airlines
12:45BOS
23:47MDW
1 StopSAR 477VIEW DEAL

Boston to Chicago monthly flight fare trend

Aug
from SAR 281
Sep
from SAR 285
Oct
from SAR 281
Nov
from SAR 363
Dec
from SAR 507
Jan
No flights

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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