Chicago to Boston
ORDBOS
Fly from Chicago to Boston starting at USD 86 with B6.
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
B6
09:50ORD
--:--BOS
Direct$196VIEW DEAL
25 Apr
F9
16:28ORD
--:--BOS
1 Stop$268VIEW DEAL
27 Apr
AA
08:41ORD
--:--BOS
1 Stop$143VIEW DEAL
28 Apr
AA
08:05ORD
--:--BOS
Direct$98VIEW DEAL
29 Apr
AA
06:00ORD
--:--BOS
Direct$101VIEW DEAL
30 Apr
AA
13:11ORD
--:--BOS
Direct$95VIEW DEAL
12 May
B6
09:49ORD
--:--BOS
Direct$86VIEW DEAL
14 May
UA
06:00ORD
--:--BOS
Direct$88VIEW DEAL
5 Jul
AA
07:00ORD
--:--BOS
Direct$158VIEW DEAL
Chicago to Boston monthly flight fare trend
Apr
from USD 95
May
from USD 86
Jun
No flights
Jul
from USD 158
Aug
No flights
Sep
No flights
Airport Details
Origin
Chicago
Chicago O'Hare International Airport (ORD)
Chicago, ORD
Zone
Chicago
Elev
680 ft
Destination
Boston
Logan International Airport (BOS)
Boston, BOS
Zone
New York
Elev
20 ft
