Chicago to Boston

MDWBOS

Fly from Chicago to Boston starting at SAR 318 with Southwest Airlines.Best fare available on Jul 30, 2026.Limited seats. Better plans. Book before it's gone.

Chicago to Boston cheapest flights this week

30 Jul
Southwest Airlines
19:35MDW
21:55BOS
DirectSAR 318VIEW DEAL
31 Jul
Southwest Airlines
19:35MDW
21:55BOS
DirectSAR 511VIEW DEAL
1 Aug
Southwest Airlines
17:45MDW
20:10BOS
DirectSAR 507VIEW DEAL
2 Aug
Southwest Airlines
05:15MDW
07:25BOS
DirectSAR 322VIEW DEAL
5 Aug
Southwest Airlines
09:25MDW
15:00BOS
1 StopSAR 470VIEW DEAL
5 Aug
Southwest Airlines
12:50MDW
15:10BOS
DirectSAR 548VIEW DEAL
6 Aug
Southwest Airlines
05:45MDW
08:00BOS
DirectSAR 518VIEW DEAL
6 Aug
Southwest Airlines
18:30MDW
20:50BOS
DirectSAR 544VIEW DEAL
8 Aug
Southwest Airlines
15:10MDW
17:30BOS
DirectSAR 507VIEW DEAL
8 Aug
Southwest Airlines
12:30MDW
20:40BOS
2 StopSAR 448VIEW DEAL

Chicago to Boston monthly flight fare trend

Jul
from SAR 318
Aug
from SAR 285
Sep
from SAR 366
Oct
from SAR 411
Nov
No flights
Dec
from SAR 448

Airport Details

Origin

Chicago

Chicago Midway International Airport (MDW)

Chicago, MDW
Zone

Chicago

Elev

620 ft

Destination

Boston

Logan International Airport (BOS)

Boston, BOS
Zone

New York

Elev

20 ft

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