Boston to Chicago

BOSMDW

Fly from Boston to Chicago starting at SAR 366 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 StopSAR 548VIEW DEAL
17 Nov
Frontier Airlines
12:15BOS
18:47MDW
1 StopSAR 570VIEW DEAL
18 Nov
Frontier Airlines
12:39BOS
00:47MDW
1 StopSAR 544VIEW DEAL
19 Nov
Frontier Airlines
12:39BOS
00:47MDW
1 StopSAR 503VIEW DEAL
21 Nov
Frontier Airlines
11:06BOS
20:47MDW
1 StopSAR 481VIEW DEAL
26 Nov
Southwest Airlines
07:45BOS
17:20MDW
1 StopSAR 514VIEW DEAL
27 Nov
Southwest Airlines
07:05BOS
09:50MDW
DirectSAR 566VIEW DEAL
1 Dec
Southwest Airlines
12:50BOS
15:40MDW
DirectSAR 614VIEW DEAL
7 Dec
Frontier Airlines
11:08BOS
21:42MDW
1 StopSAR 366VIEW DEAL
8 Dec
Southwest Airlines
12:50BOS
15:40MDW
DirectSAR 377VIEW DEAL

Boston to Chicago monthly flight fare trend

Nov
from SAR 481
Dec
from SAR 366
Jan
from SAR 522
Feb
from SAR 644
Mar
from SAR 633
Apr
from SAR 607

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

Flights from Boston

Flights from Boston to AtlantaFlights from Boston to AustinFlights from Boston to CharlotteFlights from Boston to DenverFlights from Boston to DallasFlights from Boston to DetroitFlights from Boston to NewarkFlights from Boston to Fort LauderdaleFlights from Boston to HonoluluFlights from Boston to Washington