Chicago to Boston

MDWBOS

Fly from Chicago to Boston starting at SAR 355 with Southwest Airlines.Best fare available on Sep 2, 2026.Limited seats. Better plans. Book before it's gone.

Chicago to Boston cheapest flights this week

2 Sept
Southwest Airlines
18:00MDW
20:20BOS
DirectSAR 429VIEW DEAL
2 Sept
Southwest Airlines
12:50MDW
15:10BOS
DirectSAR 722VIEW DEAL
2 Sept
Southwest Airlines
09:25MDW
15:00BOS
1 StopSAR 355VIEW DEAL
2 Sept
Southwest Airlines
06:40MDW
08:55BOS
DirectSAR 448VIEW DEAL
3 Sept
Southwest Airlines
05:45MDW
08:00BOS
DirectSAR 588VIEW DEAL
4 Sept
Southwest Airlines
05:45MDW
08:00BOS
DirectSAR 648VIEW DEAL
5 Sept
Southwest Airlines
07:55MDW
20:45BOS
2 StopSAR 633VIEW DEAL
5 Sept
Southwest Airlines
07:40MDW
10:00BOS
DirectSAR 699VIEW DEAL
6 Sept
Southwest Airlines
08:45MDW
11:15BOS
DirectSAR 544VIEW DEAL
7 Sept
Southwest Airlines
05:45MDW
08:00BOS
DirectSAR 448VIEW DEAL

Chicago to Boston monthly flight fare trend

Sep
from SAR 355
Oct
from SAR 411
Nov
from SAR 414
Dec
from SAR 448
Jan
No flights
Feb
No flights

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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