Boston to Chicago

BOSMDW

Fly from Boston to Chicago starting at USD 117 with Frontier Airlines.Best fare available on Jun 21, 2026.Limited seats. Better plans. Book before it's gone.

Boston to Chicago cheapest flights this week

21 Jun
Frontier Airlines
06:00BOS
12:12MDW
1 Stop$117VIEW DEAL
28 Jun
Southwest Airlines
22:05BOS
00:45MDW
Direct$141VIEW DEAL
29 Jun
Frontier Airlines
06:00BOS
12:09MDW
1 Stop$126VIEW DEAL
31 Jul
Frontier Airlines
06:00BOS
12:09MDW
1 Stop$147VIEW DEAL
28 Sept
Southwest Airlines
09:40BOS
17:15MDW
1 Stop$214VIEW DEAL

Boston to Chicago monthly flight fare trend

May
from USD 97
Jun
from USD 117
Jul
from USD 147
Aug
No flights
Sep
from USD 214
Oct
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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