Boston to Chicago
BOSORD
Fly from Boston to Chicago starting at USD 86 with B6.
Best fare available on May 12, 2026.
Limited seats. Better plans. Book before it's gone.
Boston to Chicago cheapest flights this week
20 Apr
AA
12:22BOS
--:--ORD
Direct$234VIEW DEAL
22 Apr
AA
06:30BOS
--:--ORD
Direct$102VIEW DEAL
23 Apr
AA
06:30BOS
--:--ORD
Direct$100VIEW DEAL
24 Apr
AA
15:59BOS
--:--ORD
Direct$99VIEW DEAL
25 Apr
UA
11:00BOS
--:--ORD
Direct$108VIEW DEAL
26 Apr
AA
06:30BOS
--:--ORD
Direct$99VIEW DEAL
28 Apr
AA
12:22BOS
--:--ORD
Direct$99VIEW DEAL
29 Apr
AA
10:32BOS
--:--ORD
Direct$98VIEW DEAL
3 May
AA
08:03BOS
--:--ORD
Direct$90VIEW DEAL
12 May
B6
18:47BOS
--:--ORD
Direct$86VIEW DEAL
Boston to Chicago monthly flight fare trend
Apr
from USD 98
May
from USD 83
Jun
from USD 82
Jul
from USD 111
Aug
No flights
Sep
from USD 108
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
