Boston to Chicago

BOSMDW

Fly from Boston to Chicago starting at USD 76 with Southwest Airlines.Best fare available on Aug 25, 2026.Limited seats. Better plans. Book before it's gone.

Boston to Chicago cheapest flights this week

21 Aug
Frontier Airlines
12:45BOS
23:47MDW
1 StopUSD 125VIEW DEAL
22 Aug
Frontier Airlines
12:45BOS
23:47MDW
1 StopUSD 134VIEW DEAL
23 Aug
Southwest Airlines
07:30BOS
10:05MDW
DirectUSD 181VIEW DEAL
25 Aug
Southwest Airlines
19:15BOS
21:50MDW
DirectUSD 76VIEW DEAL
25 Aug
Frontier Airlines
12:45BOS
23:47MDW
1 StopUSD 124VIEW DEAL
26 Aug
Frontier Airlines
12:45BOS
23:47MDW
1 StopUSD 135VIEW DEAL
27 Aug
Southwest Airlines
12:40BOS
15:10MDW
DirectUSD 115VIEW DEAL
28 Aug
Frontier Airlines
12:45BOS
23:47MDW
1 StopUSD 124VIEW DEAL
29 Aug
Southwest Airlines
15:25BOS
18:00MDW
DirectUSD 115VIEW DEAL
30 Aug
Southwest Airlines
21:05BOS
23:40MDW
DirectUSD 89VIEW DEAL

Boston to Chicago monthly flight fare trend

Aug
from USD 76
Sep
from USD 77
Oct
from USD 76
Nov
from USD 98
Dec
from USD 137
Jan
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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