Boston to Chicago
BOSORD
Fly from Boston to Chicago starting at SAR 311 with AA.
Best fare available on May 17, 2026.
Limited seats. Better plans. Book before it's gone.
Boston to Chicago cheapest flights this week
22 Apr
AA
06:30BOS
13:44ORD
DirectSAR 383VIEW DEAL
23 Apr
AA
06:30BOS
13:44ORD
DirectSAR 375VIEW DEAL
24 Apr
AA
15:59BOS
23:13ORD
DirectSAR 371VIEW DEAL
25 Apr
UA
11:00BOS
17:59ORD
DirectSAR 405VIEW DEAL
26 Apr
AA
06:30BOS
13:44ORD
DirectSAR 371VIEW DEAL
28 Apr
AA
12:22BOS
19:25ORD
DirectSAR 371VIEW DEAL
29 Apr
AA
10:32BOS
17:40ORD
DirectSAR 368VIEW DEAL
3 May
AA
08:03BOS
15:12ORD
DirectSAR 338VIEW DEAL
12 May
B6
18:47BOS
01:53ORD
DirectSAR 323VIEW DEAL
17 May
AA
06:30BOS
13:44ORD
DirectSAR 311VIEW DEAL
Boston to Chicago monthly flight fare trend
Apr
from SAR 368
May
from SAR 311
Jun
from SAR 308
Jul
from SAR 416
Aug
No flights
Sep
from SAR 405
Airport Details
Origin
Boston
Logan International Airport (BOS)
Boston, BOS
Zone
New York
Elev
20 ft
Destination
Chicago
Chicago O'Hare International Airport (ORD)
Chicago, ORD
Zone
Chicago
Elev
680 ft
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