Boston to Chicago
BOSMDW
Fly from Boston to Chicago starting at SAR 364 with WN.
Best fare available on May 12, 2026.
Limited seats. Better plans. Book before it's gone.
Boston to Chicago cheapest flights this week
22 Apr
WN
07:20BOS
14:05MDW
DirectSAR 424VIEW DEAL
23 Apr
WN
10:40BOS
17:20MDW
DirectSAR 409VIEW DEAL
24 Apr
WN
15:45BOS
22:30MDW
DirectSAR 398VIEW DEAL
25 Apr
WN
13:50BOS
20:30MDW
DirectSAR 416VIEW DEAL
26 Apr
WN
06:10BOS
12:55MDW
DirectSAR 413VIEW DEAL
28 Apr
WN
10:45BOS
17:25MDW
DirectSAR 413VIEW DEAL
29 Apr
WN
18:20BOS
01:10MDW
DirectSAR 398VIEW DEAL
3 May
F9
10:53BOS
12:46MDW
1 StopSAR 379VIEW DEAL
12 May
WN
14:25BOS
21:05MDW
DirectSAR 364VIEW DEAL
17 May
WN
06:10BOS
12:55MDW
DirectSAR 439VIEW DEAL
Boston to Chicago monthly flight fare trend
Apr
from SAR 398
May
from SAR 364
Jun
from SAR 439
Jul
from SAR 551
Aug
No flights
Sep
from SAR 803
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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