Boston to Chicago
BOSMDW
Fly from Boston to Chicago starting at USD 97 with WN.
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
WN
10:40BOS
--:--MDW
Direct$249VIEW DEAL
22 Apr
WN
07:20BOS
--:--MDW
Direct$113VIEW DEAL
23 Apr
WN
10:40BOS
--:--MDW
Direct$109VIEW DEAL
24 Apr
WN
15:45BOS
--:--MDW
Direct$106VIEW DEAL
25 Apr
WN
13:50BOS
--:--MDW
Direct$111VIEW DEAL
26 Apr
WN
06:10BOS
--:--MDW
Direct$110VIEW DEAL
28 Apr
WN
10:45BOS
--:--MDW
Direct$110VIEW DEAL
29 Apr
WN
18:20BOS
--:--MDW
Direct$106VIEW DEAL
3 May
F9
10:53BOS
--:--MDW
1 Stop$101VIEW DEAL
12 May
WN
14:25BOS
--:--MDW
Direct$97VIEW DEAL
Boston to Chicago monthly flight fare trend
Apr
from USD 106
May
from USD 97
Jun
from USD 117
Jul
from USD 147
Aug
No flights
Sep
from USD 214
Airport Details
Origin
Boston
Logan International Airport (BOS)
Boston, BOS
Zone
New York
Elev
20 ft
Destination
Chicago
Chicago Midway International Airport (MDW)
Chicago, MDW
Zone
Chicago
Elev
620 ft
