Denver to Chicago

DENMDW

Fly from Denver to Chicago starting at USD 78 with Southwest Airlines.Best fare available on Aug 10, 2026.Limited seats. Better plans. Book before it's gone.

Denver to Chicago cheapest flights this week

15 Jul
Frontier Airlines
05:05DEN
14:50MDW
1 StopUSD 148VIEW DEAL
24 Jul
Frontier Airlines
10:09DEN
16:22MDW
1 StopUSD 152VIEW DEAL
25 Jul
Frontier Airlines
10:09DEN
16:26MDW
1 StopUSD 152VIEW DEAL
27 Jul
Frontier Airlines
23:59DEN
10:07MDW
1 StopUSD 158VIEW DEAL
6 Aug
Southwest Airlines
07:00DEN
09:20MDW
DirectUSD 135VIEW DEAL
10 Aug
Southwest Airlines
20:25DEN
22:45MDW
DirectUSD 78VIEW DEAL
4 Sept
Frontier Airlines
10:09DEN
19:31MDW
1 StopUSD 130VIEW DEAL
13 Sept
Frontier Airlines
23:59DEN
09:58MDW
1 StopUSD 136VIEW DEAL
24 Nov
Southwest Airlines
20:50DEN
23:05MDW
DirectUSD 140VIEW DEAL
25 Nov
Southwest Airlines
05:05DEN
07:25MDW
DirectUSD 130VIEW DEAL

Denver to Chicago monthly flight fare trend

Jul
from USD 148
Aug
from USD 78
Sep
from USD 130
Oct
No flights
Nov
from USD 130
Dec
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

Flights from Denver

Flights from Denver to AtlantaFlights from Denver to AustinFlights from Denver to BostonFlights from Denver to CharlotteFlights from Denver to DallasFlights from Denver to DetroitFlights from Denver to NewarkFlights from Denver to Fort LauderdaleFlights from Denver to HonoluluFlights from Denver to Washington