Chicago to Boston

MDWBOS

Fly from Chicago to Boston starting at USD 90 with Southwest Airlines.Best fare available on Nov 18, 2026.Limited seats. Better plans. Book before it's gone.

Chicago to Boston cheapest flights this week

15 Nov
Southwest Airlines
20:25MDW
07:20BOS
1 StopUSD 218VIEW DEAL
17 Nov
Southwest Airlines
08:30MDW
11:00BOS
DirectUSD 205VIEW DEAL
18 Nov
Southwest Airlines
08:30MDW
11:00BOS
DirectUSD 90VIEW DEAL
18 Nov
Southwest Airlines
13:15MDW
15:20BOS
DirectUSD 201VIEW DEAL
19 Nov
Southwest Airlines
08:30MDW
11:00BOS
DirectUSD 155VIEW DEAL
20 Nov
Frontier Airlines
20:42MDW
09:11BOS
1 StopUSD 176VIEW DEAL
21 Nov
Southwest Airlines
17:50MDW
22:45BOS
1 StopUSD 148VIEW DEAL
21 Nov
Southwest Airlines
18:55MDW
21:15BOS
DirectUSD 154VIEW DEAL
22 Nov
Southwest Airlines
07:50MDW
10:10BOS
DirectUSD 150VIEW DEAL
22 Nov
Frontier Airlines
20:42MDW
09:11BOS
1 StopUSD 134VIEW DEAL

Chicago to Boston monthly flight fare trend

Nov
from USD 90
Dec
from USD 109
Jan
from USD 142
Feb
No flights
Mar
from USD 185
Apr
from USD 171

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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