Direct flights from Denver to Chicago DEN → MDW

Southwest Airlines flies nonstop from Denver (DEN) to Chicago (MDW), several times daily. The flight takes about 2h 21m and covers 893 miles (1,437 km). Arrivals run on time 80.3% at DEN and 72.8% at MDW — BTS data for the last three months, counting arrivals within 15 minutes of schedule. Schedule data from 20 July 2026.

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Southwest Airlines WN

Departure Schedule typical week

Typical weekly schedule · 44 flights per week (~6 per day) · Updated 41d ago

Southwest Airlines
44 flights per week (~6 per day)
Mon, Tue, Wed, Thu, Fri, Sat
05:55 → 09:20
Sat
06:10 → 09:35 07:15 → 10:35 07:50 → 11:20 10:00 → 13:25 18:25 → 22:00 20:20 → 23:45
Sun, Mon, Thu, Fri
07:10 → 10:30 13:00 → 16:20 20:50 → 00:15
Tue, Wed
07:40 → 11:05 12:00 → 15:25
Daily
15:50 → 19:15
Sun, Mon, Tue, Wed, Thu, Fri
17:35 → 21:05
Sun, Tue, Wed
19:00 → 22:30

More nonstops from Denver

DEN → SLC Salt Lake City 7 airlines DEN → ORD Chicago 6 airlines DEN → SEA Seattle 6 airlines DEN → CVG Cincinnati 5 airlines DEN → PHL Philadelphia 5 airlines DEN → PHX Phoenix 5 airlines DEN → ATL Atlanta 4 airlines DEN → ICT Wichita 4 airlines

Frequently asked questions

Is there a direct flight from Denver to Chicago?

Yes, Southwest Airlines operates nonstop flights from Denver (DEN) to Chicago (MDW).

Which airlines fly direct from Denver to Chicago?

Southwest Airlines operates nonstop flights from Denver to Chicago.

How long is the flight from Denver to Chicago?

The nonstop flight from Denver to Chicago takes ~2h 21m (approximately 1437 km).

How often do direct flights operate from Denver to Chicago?

Nonstop flights from Denver to Chicago operate multiple daily — 44 flights per week (~6 per day).

What is the on-time performance for flights from Denver to Chicago?

Arrivals run on time 80.3% at DEN and 72.8% at MDW — BTS data for the last three months, counting arrivals within 15 minutes of schedule.

What days of the week are there direct flights from Denver to Chicago?

Direct flights from Denver to Chicago operate every day of the week.

Explore More

DEN All direct flights from Denver MDW All direct flights from Chicago MDW → DEN Return: Chicago to Denver

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