Southwest Airlines
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Denver International Airport
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Midway International Airport
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Scan through all non-stop flights from Denver to Chicago. The full flight schedule below gives an overview of all non-stop flights from DEN to MDW, which includes the daily timetable of every operating airline for the upcoming 12 months.
Note: for airline-specific flight schedules, please scroll further down.
Known for its continental climate, Chicago features hot, humid summers with temperatures above 30°C (86°F) and cold, snowy winters that often drop below 0°C (32°F). This striking seasonal contrast offers travelers a variety of activities, from summer hiking to winter sports, ensuring year-round appeal.
The best time to visit Chicago is from March to November, covering spring, summer, and fall. While summer can be hot, it also sees slightly more rainfall than other seasons.
Currently, there is only one airline operating non-stop flights from Denver DEN to Chicago MDW, which is Southwest Airlines. This section gives an overview of the flight schedules and timetables of every airline with direct flights for this route.
Click an airline below to view their DEN MDW flight schedule.
Flights from DEN to MDW are operated 41 times a week, with an average of 6 flights per day. Departure times vary between 05:05 - 22:35. The earliest flight departs at 05:05, the last flight departs at 22:35. However, this depends on the date you are flying so please check with the full flight schedule above to see which departure times are available on your preferred date(s) of travel.
On this non-stop route, you can fly in Economy only.
The fastest direct flight from Denver to Chicago takes 2 hours and 25 minutes. The flight distance between Denver and Chicago is 892 miles (or 1,436 km).
There are 2 airports in Chicago: Midway International Airport (MDW) and O'Hare International Airport (ORD).
There are 41 flights per week flying from Denver to Chicago (as of October 2026).
2 hours and 25 minutes is the average flight time from Denver to Chicago.
The distance from Denver to Chicago is 892 miles (1,436 kilometers).
Southwest Airlines is the only airline flying nonstop from Denver to Chicago.
There are no alliances flying direct from Denver to Chicago at the moment.
You can fly non-stop in Economy only.
Aircraft types that fly from Denver to Chicago:
The earliest flight departs at 05:05 from Denver and arrives at 08:20 at Chicago.
The latest flight departs at 22:35 from Denver and arrives at 01:50 at Chicago.
892 miles (1,436 km) · 2h 25m
05:50
09:10
Southwest Airlines
WN 1673
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
06:25
09:45
Southwest Airlines
WN 4425
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
07:00
10:20
Southwest Airlines
WN 455
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
07:50
11:10
Southwest Airlines
WN 1674
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
08:25
11:45
Southwest Airlines
WN 1675
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
08:35
11:55
Southwest Airlines
WN 1674
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
09:30
12:50
Southwest Airlines
WN 1089
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
10:30
13:50
Southwest Airlines
WN 1675
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
10:45
14:05
Southwest Airlines
WN 427
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
10:50
14:10
Southwest Airlines
WN 1090
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
11:00
14:20
Southwest Airlines
WN 1347
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
12:50
16:05
Southwest Airlines
WN 1676
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
13:10
16:25
Southwest Airlines
WN 1676
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
13:35
16:55
Southwest Airlines
WN 1676
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
14:35
17:55
Southwest Airlines
WN 1676
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
15:20
18:40
Southwest Airlines
WN 1676
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
15:20
18:40
Southwest Airlines
WN 1091
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
15:55
19:15
Southwest Airlines
WN 3073
Southwest Airlines
Boeing 737-700
Y
W
J
F
17:35
21:00
Southwest Airlines
WN 2565
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
17:40
21:00
Southwest Airlines
WN 2565
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
17:55
21:15
Southwest Airlines
WN 2565
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
18:30
21:45
Southwest Airlines
WN 2775
Southwest Airlines
Boeing 737-700
Y
W
J
F
18:55
22:15
Southwest Airlines
WN 2775
Southwest Airlines
Boeing 737-700
Y
W
J
F
19:50
23:15
Southwest Airlines
WN 1338
Southwest Airlines
Boeing 737-700
Y
W
J
F
20:30
23:50
Southwest Airlines
WN 3047
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
20:55
00:20
Southwest Airlines
WN 1683
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
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