Chicago to Boston

MDWBOS

Fly from Chicago to Boston starting at USD 87 with Southwest Airlines.Best fare available on Aug 2, 2026.Limited seats. Better plans. Book before it's gone.

Chicago to Boston cheapest flights this week

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
5 Aug
Southwest Airlines
12:50MDW
15:10BOS
DirectUSD 148VIEW DEAL
6 Aug
Southwest Airlines
05:45MDW
08:00BOS
DirectUSD 140VIEW DEAL
6 Aug
Southwest Airlines
18:30MDW
20:50BOS
DirectUSD 147VIEW DEAL
8 Aug
Southwest Airlines
15:10MDW
17:30BOS
DirectUSD 137VIEW DEAL
8 Aug
Southwest Airlines
12:30MDW
20:40BOS
2 StopUSD 121VIEW DEAL
8 Aug
Southwest Airlines
07:40MDW
10:00BOS
DirectUSD 149VIEW DEAL
8 Aug
Southwest Airlines
09:05MDW
11:25BOS
DirectUSD 150VIEW DEAL

Chicago to Boston monthly flight fare trend

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