Chicago to Boston

MDWBOS

Fly from Chicago to Boston starting at USD 77 with Southwest Airlines.Best fare available on Aug 19, 2026.Limited seats. Better plans. Book before it's gone.

Chicago to Boston cheapest flights this week

30 Jul
Southwest Airlines
19:35MDW
21:55BOS
DirectUSD 86VIEW DEAL
31 Jul
Southwest Airlines
19:35MDW
21:55BOS
DirectUSD 137VIEW DEAL
1 Aug
Southwest Airlines
17:45MDW
20:10BOS
DirectUSD 137VIEW DEAL
2 Aug
Southwest Airlines
05:15MDW
07:25BOS
DirectUSD 87VIEW DEAL
5 Aug
Southwest Airlines
09:25MDW
15:00BOS
1 StopUSD 127VIEW DEAL
6 Aug
Southwest Airlines
05:45MDW
08:00BOS
DirectUSD 140VIEW DEAL
8 Aug
Southwest Airlines
15:10MDW
17:30BOS
DirectUSD 112VIEW DEAL
8 Aug
Southwest Airlines
12:30MDW
20:40BOS
2 StopUSD 121VIEW DEAL
16 Aug
Southwest Airlines
06:00MDW
08:15BOS
DirectUSD 85VIEW DEAL
19 Aug
Southwest Airlines
06:40MDW
08:55BOS
DirectUSD 77VIEW DEAL

Chicago to Boston monthly flight fare trend

Jul
from USD 86
Aug
from USD 77
Sep
from USD 99
Oct
from USD 111
Nov
No flights
Dec
from USD 121

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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