Boston to Chicago
BOSORD
Fly from Boston to Chicago starting at USD 82 with AA.
Best fare available on Jun 29, 2026.
Limited seats. Better plans. Book before it's gone.
Boston to Chicago cheapest flights this week
12 May
B6
18:47BOS
21:53ORD
Direct$86VIEW DEAL
17 May
AA
06:30BOS
09:44ORD
Direct$83VIEW DEAL
21 Jun
AA
05:05BOS
08:03ORD
Direct$97VIEW DEAL
28 Jun
AA
05:05BOS
08:03ORD
Direct$96VIEW DEAL
29 Jun
AA
05:05BOS
08:03ORD
Direct$82VIEW DEAL
31 Jul
AA
05:00BOS
07:55ORD
Direct$111VIEW DEAL
28 Sept
B6
17:00BOS
20:22ORD
Direct$108VIEW DEAL
22 Mar
AC
14:45BOS
21:16ORD
1 Stop$511VIEW DEAL
Boston to Chicago monthly flight fare trend
May
from USD 83
Jun
from USD 82
Jul
from USD 111
Aug
No flights
Sep
from USD 108
Oct
No flights
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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