Chicago to Boston
MDWBOS
Fly from Chicago to Boston starting at USD 94 with WN.
Best fare available on May 12, 2026.
Limited seats. Better plans. Book before it's gone.
Chicago to Boston cheapest flights this week
12 May
WN
15:15MDW
17:35BOS
Direct$94VIEW DEAL
14 May
F9
12:19MDW
00:24BOS
1 Stop$102VIEW DEAL
5 Jul
WN
05:15MDW
07:25BOS
Direct$108VIEW DEAL
Chicago to Boston monthly flight fare trend
May
from USD 94
Jun
No flights
Jul
from USD 108
Aug
No flights
Sep
No flights
Oct
No flights
Airport Details
Origin
Chicago
Chicago Midway International Airport (MDW)
Chicago, MDW
Zone
Chicago
Elev
620 ft
Destination
Boston
Logan International Airport (BOS)
Boston, BOS
Zone
New York
Elev
20 ft
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