Boston to Chicago

BOSMDW

Fly from Boston to Chicago starting at USD 77 with Southwest Airlines.Best fare available on Sep 10, 2026.Limited seats. Better plans. Book before it's gone.

Boston to Chicago cheapest flights this week

10 Sept
Southwest Airlines
18:40BOS
21:20MDW
DirectUSD 77VIEW DEAL
10 Sept
Frontier Airlines
12:54BOS
00:44MDW
1 StopUSD 141VIEW DEAL
11 Sept
Frontier Airlines
12:54BOS
18:51MDW
1 StopUSD 135VIEW DEAL
12 Sept
Frontier Airlines
12:54BOS
18:51MDW
1 StopUSD 143VIEW DEAL
13 Sept
Southwest Airlines
07:30BOS
10:05MDW
DirectUSD 158VIEW DEAL
13 Sept
Southwest Airlines
05:30BOS
10:55MDW
1 StopUSD 201VIEW DEAL
15 Sept
Southwest Airlines
10:05BOS
12:35MDW
DirectUSD 112VIEW DEAL
15 Sept
Southwest Airlines
19:15BOS
21:55MDW
DirectUSD 88VIEW DEAL
15 Sept
Southwest Airlines
15:20BOS
17:55MDW
DirectUSD 135VIEW DEAL
16 Sept
Southwest Airlines
07:30BOS
10:05MDW
DirectUSD 172VIEW DEAL

Boston to Chicago monthly flight fare trend

Sep
from USD 77
Oct
from USD 76
Nov
from USD 98
Dec
from USD 113
Jan
from USD 141
Feb
No flights

Airport Details

Origin

Boston

Logan International Airport (BOS)

Boston, BOS
Zone

New York

Elev

20 ft

Destination

Chicago

Chicago Midway International Airport (MDW)

Chicago, MDW
Zone

Chicago

Elev

620 ft

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