Chicago to Boston
MDWBOS
Fly from Chicago to Boston starting at SAR 353 with WN.
Best fare available on May 12, 2026.
Limited seats. Better plans. Book before it's gone.
Chicago to Boston cheapest flights this week
24 Apr
F9
14:15MDW
11:40BOS
2 StopSAR 975VIEW DEAL
25 Apr
F9
09:14MDW
05:31BOS
2 StopSAR 1,204VIEW DEAL
27 Apr
WN
18:25MDW
13:45BOS
2 StopSAR 780VIEW DEAL
28 Apr
WN
18:00MDW
01:20BOS
DirectSAR 398VIEW DEAL
29 Apr
WN
12:45MDW
20:05BOS
DirectSAR 398VIEW DEAL
30 Apr
WN
09:25MDW
16:40BOS
DirectSAR 443VIEW DEAL
12 May
WN
15:15MDW
22:35BOS
DirectSAR 353VIEW DEAL
14 May
F9
12:19MDW
05:24BOS
1 StopSAR 383VIEW DEAL
5 Jul
WN
05:15MDW
12:25BOS
DirectSAR 405VIEW DEAL
Chicago to Boston monthly flight fare trend
Apr
from SAR 398
May
from SAR 353
Jun
No flights
Jul
from SAR 405
Aug
No flights
Sep
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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