Dallas to Chicago

DALMDW

Fly from Dallas to Chicago starting at USD 152 with Southwest Airlines.Best fare available on Sep 25, 2026.Limited seats. Better plans. Book before it's gone.

Dallas to Chicago cheapest flights this week

23 Sept
Southwest Airlines
06:15DAL
23:15MDW
2 StopUSD 639VIEW DEAL
24 Sept
Southwest Airlines
10:40DAL
12:50MDW
DirectUSD 290VIEW DEAL
24 Sept
Southwest Airlines
21:10DAL
23:25MDW
DirectUSD 312VIEW DEAL
25 Sept
Southwest Airlines
06:00DAL
08:10MDW
DirectUSD 152VIEW DEAL
25 Sept
Southwest Airlines
21:10DAL
23:25MDW
DirectUSD 286VIEW DEAL
25 Sept
Southwest Airlines
15:25DAL
19:25MDW
DirectUSD 160VIEW DEAL
26 Sept
Southwest Airlines
09:40DAL
11:50MDW
DirectUSD 198VIEW DEAL
27 Sept
Southwest Airlines
19:45DAL
22:00MDW
DirectUSD 290VIEW DEAL
28 Sept
Southwest Airlines
21:10DAL
23:25MDW
DirectUSD 287VIEW DEAL
29 Sept
Southwest Airlines
18:30DAL
20:45MDW
DirectUSD 241VIEW DEAL

Dallas to Chicago monthly flight fare trend

Sep
from USD 152
Oct
from USD 152
Nov
from USD 153
Dec
from USD 166
Jan
No flights
Feb
No flights

Airport Details

Origin

Dallas

Dallas Love Field (DAL)

Dallas, DAL
Zone

Chicago

Elev

487 ft

Destination

Chicago

Chicago Midway International Airport (MDW)

Chicago, MDW
Zone

Chicago

Elev

620 ft