Chicago to Boston

MDWBOS

Fly from Chicago to Boston starting at USD 159 with Southwest Airlines.Best fare available on Sep 30, 2026.Limited seats. Better plans. Book before it's gone.

Chicago to Boston cheapest flights this week

30 Sept
Southwest Airlines
06:40MDW
08:55BOS
DirectUSD 159VIEW DEAL
30 Sept
Southwest Airlines
08:45MDW
11:15BOS
DirectUSD 208VIEW DEAL
30 Sept
Southwest Airlines
12:45MDW
17:35BOS
1 StopUSD 217VIEW DEAL
1 Oct
Southwest Airlines
05:30MDW
07:55BOS
DirectUSD 212VIEW DEAL
1 Oct
Southwest Airlines
18:25MDW
23:05BOS
1 StopUSD 196VIEW DEAL
2 Oct
Southwest Airlines
11:00MDW
16:20BOS
1 StopUSD 196VIEW DEAL
2 Oct
Southwest Airlines
15:30MDW
17:50BOS
DirectUSD 215VIEW DEAL
3 Oct
Southwest Airlines
08:00MDW
10:20BOS
DirectUSD 180VIEW DEAL
4 Oct
Southwest Airlines
05:00MDW
07:25BOS
DirectUSD 181VIEW DEAL
7 Oct
Southwest Airlines
09:10MDW
11:30BOS
DirectUSD 188VIEW DEAL

Chicago to Boston monthly flight fare trend

Sep
from USD 159
Oct
from USD 98
Nov
from USD 90
Dec
from USD 109
Jan
from USD 142
Feb
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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