Denver to Chicago

DENMDW

Fly from Denver to Chicago starting at USD 106 with Southwest Airlines.Best fare available on Sep 30, 2026.Limited seats. Better plans. Book before it's gone.

Denver to Chicago cheapest flights this week

30 Sept
Southwest Airlines
19:25DEN
21:55MDW
DirectUSD 106VIEW DEAL
1 Oct
Southwest Airlines
05:50DEN
08:10MDW
DirectUSD 118VIEW DEAL
3 Oct
Frontier Airlines
10:44DEN
16:51MDW
1 StopUSD 218VIEW DEAL
3 Oct
Southwest Airlines
06:55DEN
11:05MDW
1 StopUSD 119VIEW DEAL
4 Oct
Frontier Airlines
10:44DEN
16:46MDW
1 StopUSD 133VIEW DEAL
5 Oct
Frontier Airlines
10:44DEN
16:51MDW
1 StopUSD 210VIEW DEAL
5 Oct
Southwest Airlines
05:50DEN
08:10MDW
DirectUSD 118VIEW DEAL
5 Oct
Southwest Airlines
20:55DEN
23:20MDW
DirectUSD 111VIEW DEAL
6 Oct
Frontier Airlines
10:44DEN
16:46MDW
1 StopUSD 119VIEW DEAL
7 Oct
Southwest Airlines
07:00DEN
09:20MDW
DirectUSD 142VIEW DEAL

Denver to Chicago monthly flight fare trend

Sep
from USD 106
Oct
from USD 102
Nov
from USD 110
Dec
from USD 112
Jan
No flights
Feb
No flights

Airport Details

Origin

Denver

Denver International Airport (DEN)

Denver, DEN
Zone

Denver

Elev

5431 ft

Destination

Chicago

Chicago Midway International Airport (MDW)

Chicago, MDW
Zone

Chicago

Elev

620 ft

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