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
24 Apr
F9
14:15MDW
--:--BOS
2 Stop$260VIEW DEAL
25 Apr
F9
09:14MDW
--:--BOS
2 Stop$321VIEW DEAL
27 Apr
WN
18:25MDW
--:--BOS
2 Stop$208VIEW DEAL
28 Apr
WN
18:00MDW
--:--BOS
Direct$106VIEW DEAL
29 Apr
WN
12:45MDW
--:--BOS
Direct$106VIEW DEAL
30 Apr
WN
09:25MDW
--:--BOS
Direct$118VIEW DEAL
12 May
WN
15:15MDW
--:--BOS
Direct$94VIEW DEAL
14 May
F9
12:19MDW
--:--BOS
1 Stop$102VIEW DEAL
5 Jul
WN
05:15MDW
--:--BOS
Direct$108VIEW DEAL
Chicago to Boston monthly flight fare trend
Apr
from USD 106
May
from USD 94
Jun
No flights
Jul
from USD 108
Aug
No flights
Sep
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
