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
12 May
WN
14:25BOS
17:05MDW
Direct$97VIEW DEAL
17 May
WN
06:10BOS
08:55MDW
Direct$117VIEW DEAL
21 Jun
F9
06:00BOS
12:12MDW
1 Stop$117VIEW DEAL
28 Jun
WN
22:05BOS
00:45MDW
Direct$141VIEW DEAL
29 Jun
F9
06:00BOS
12:09MDW
1 Stop$126VIEW DEAL
31 Jul
F9
06:00BOS
12:09MDW
1 Stop$147VIEW DEAL
28 Sept
WN
09:40BOS
17:15MDW
1 Stop$214VIEW DEAL
Boston to Chicago monthly flight fare trend
May
from USD 97
Jun
from USD 117
Jul
from USD 147
Aug
No flights
Sep
from USD 214
Oct
No flights
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
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