Boston to Chicago

BOSMDW

Fly from Boston to Chicago starting at USD 99 with Frontier Airlines.Best fare available on Dec 7, 2026.Limited seats. Better plans. Book before it's gone.

Boston to Chicago cheapest flights this week

13 Nov
Frontier Airlines
12:39BOS
00:47MDW
1 StopUSD 148VIEW DEAL
17 Nov
Frontier Airlines
12:15BOS
18:47MDW
1 StopUSD 154VIEW DEAL
18 Nov
Frontier Airlines
12:39BOS
00:47MDW
1 StopUSD 147VIEW DEAL
19 Nov
Frontier Airlines
12:39BOS
00:47MDW
1 StopUSD 136VIEW DEAL
21 Nov
Frontier Airlines
11:06BOS
20:47MDW
1 StopUSD 130VIEW DEAL
26 Nov
Southwest Airlines
07:45BOS
17:20MDW
1 StopUSD 139VIEW DEAL
27 Nov
Southwest Airlines
07:05BOS
09:50MDW
DirectUSD 153VIEW DEAL
1 Dec
Southwest Airlines
12:50BOS
15:40MDW
DirectUSD 166VIEW DEAL
7 Dec
Frontier Airlines
11:08BOS
21:42MDW
1 StopUSD 99VIEW DEAL
8 Dec
Southwest Airlines
12:50BOS
15:40MDW
DirectUSD 102VIEW DEAL

Boston to Chicago monthly flight fare trend

Nov
from USD 130
Dec
from USD 99
Jan
from USD 141
Feb
from USD 174
Mar
from USD 171
Apr
from USD 164

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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