Denver to Chicago

DENMDW

Fly from Denver to Chicago starting at USD 91 with Southwest Airlines.Best fare available on Sep 10, 2026.Limited seats. Better plans. Book before it's gone.

Denver to Chicago cheapest flights this week

10 Sept
Southwest Airlines
20:25DEN
22:50MDW
DirectUSD 91VIEW DEAL
10 Sept
Frontier Airlines
10:44DEN
16:46MDW
1 StopUSD 146VIEW DEAL
10 Sept
Frontier Airlines
22:44DEN
22:44MDW
2 StopUSD 445VIEW DEAL
11 Sept
Frontier Airlines
07:30DEN
19:15MDW
3 StopUSD 429VIEW DEAL
12 Sept
Frontier Airlines
22:44DEN
10:59MDW
2 StopUSD 386VIEW DEAL
13 Sept
Frontier Airlines
23:59DEN
09:58MDW
1 StopUSD 136VIEW DEAL
13 Sept
Southwest Airlines
06:10DEN
08:35MDW
DirectUSD 328VIEW DEAL
14 Sept
Southwest Airlines
18:30DEN
21:00MDW
DirectUSD 328VIEW DEAL
15 Sept
Frontier Airlines
10:44DEN
16:46MDW
1 StopUSD 185VIEW DEAL
16 Sept
Southwest Airlines
11:00DEN
16:00MDW
1 StopUSD 158VIEW DEAL

Denver to Chicago monthly flight fare trend

Sep
from USD 91
Oct
from USD 105
Nov
from USD 110
Dec
from USD 122
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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