Denver to Chicago

DENMDW

Fly from Denver to Chicago starting at USD 108 with Southwest Airlines.Best fare available on Aug 24, 2026.Limited seats. Better plans. Book before it's gone.

Denver to Chicago cheapest flights this week

18 Aug
Southwest Airlines
19:25DEN
21:50MDW
DirectUSD 109VIEW DEAL
20 Aug
Frontier Airlines
10:09DEN
19:31MDW
1 StopUSD 175VIEW DEAL
21 Aug
Southwest Airlines
20:25DEN
22:45MDW
DirectUSD 125VIEW DEAL
22 Aug
Frontier Airlines
10:43DEN
21:47MDW
1 StopUSD 156VIEW DEAL
23 Aug
Frontier Airlines
23:59DEN
09:55MDW
1 StopUSD 175VIEW DEAL
24 Aug
Southwest Airlines
18:30DEN
21:00MDW
DirectUSD 108VIEW DEAL
24 Aug
Frontier Airlines
23:59DEN
09:55MDW
1 StopUSD 171VIEW DEAL
25 Aug
Southwest Airlines
08:25DEN
10:50MDW
DirectUSD 117VIEW DEAL
25 Aug
Frontier Airlines
23:59DEN
09:55MDW
1 StopUSD 144VIEW DEAL
28 Aug
Frontier Airlines
10:09DEN
19:31MDW
1 StopUSD 174VIEW DEAL

Denver to Chicago monthly flight fare trend

Aug
from USD 108
Sep
from USD 83
Oct
from USD 89
Nov
from USD 130
Dec
from USD 122
Jan
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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