Denver to Chicago

DENMDW

Fly from Denver to Chicago starting at USD 141 with Southwest Airlines.Best fare available on Oct 13, 2026.Limited seats. Better plans. Book before it's gone.

Denver to Chicago cheapest flights this week

11 Oct
Frontier Airlines
10:38DEN
16:45MDW
1 StopUSD 291VIEW DEAL
12 Oct
Southwest Airlines
05:50DEN
08:10MDW
DirectUSD 298VIEW DEAL
12 Oct
Frontier Airlines
10:38DEN
22:43MDW
1 StopUSD 205VIEW DEAL
12 Oct
Southwest Airlines
18:55DEN
21:15MDW
DirectUSD 280VIEW DEAL
13 Oct
Southwest Airlines
19:50DEN
22:15MDW
DirectUSD 272VIEW DEAL
13 Oct
Southwest Airlines
07:00DEN
09:20MDW
DirectUSD 240VIEW DEAL
13 Oct
Southwest Airlines
17:40DEN
20:00MDW
DirectUSD 141VIEW DEAL
13 Oct
Frontier Airlines
10:38DEN
22:43MDW
1 StopUSD 240VIEW DEAL
13 Oct
Southwest Airlines
13:35DEN
15:55MDW
DirectUSD 248VIEW DEAL
14 Oct
Southwest Airlines
07:00DEN
09:20MDW
DirectUSD 142VIEW DEAL

Denver to Chicago monthly flight fare trend

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

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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