Flights from Denver (DEN) to Chicago (MDW)

Want to trade the Mile High City for the Windy City for a spell? Southwest Airlines® has flights from Denver International Airport to Chicago Midway International Airport at prices that'll make it easier to part with the purple mountain majesties of the Rockies. Find your flight from Denver to Chicago (Midway) with Southwest® and book with confidence—get ready for cheap, enjoyable travel. If your upcoming trip has flexible dates, search for flights with the Low Fare Calendar to discover the cheapest flights in your date range. Want more savings? Explore Southwest Vacations® to see deals on flights, hotels, rental cars, and packages.

Explore our available Denver to Chicago (Midway) flights and book your next trip!


Best Airline in the US and North America

Check out Denver to Chicago (Midway) flights and book yours now!

Flight Details

Average Flight Time: 2 hours 15 minutes

Departing from: Denver International Airport (DEN)

Arriving at: Chicago Midway International Airport (MDW)


Route Information


Nonstop flightsper day


Daily flights


Weekly flights


Flights before noon


Flights between


Flights after 6pm

Other popular flights from Denver

View our interactive map

Explore Chicago

Whether for business or pleasure, Chicago may be calling you away from Denver. While you won't get the same kind of altitude when you visit, you can summit the highest building in the Western hemisphere—Willis Tower (or Sears Tower, as locals still call it). From the famous Skydeck Chicago Ledge, daredevils can step out onto a glass floor 1,353 ft. above the hustle and bustle of the streets below. It's not quite the Rocky Mountain high you're used to, but it's still a thrill. Looking for something at sea level? Check out the walking or boat tour. Several are based downtown, but many venture into one of the city's 77 designated neighborhood areas.

Maybe you're after a slice of famous Chicago-style pizza. Contrary to popular belief, deep dish isn't the only game in town. In fact, there are two kinds of ooey-gooey, larger-than-life pizza styles: deep dish and stuffed. However, Chicago natives actually call thin-and-crispy “party cut” or “tavern style” pizza true Chicago-style pie. Less crunchy than St. Louis crust, more crispy than a New York City-style slice, the choice of real Chicagoans is sure to please. If your stomach can manage it, sample a slice of each after you land at Midway—or have a pie shipped home to Denver.

Of course, there's much more to do when you land in Chicago than eat and see the landmarks. No matter how you choose to spend your time, flying from Denver to Chicago (Midway) with Southwest Airlines keeps travel costs down and makes booking a breeze.

Travel Tips


Infant Policy

One child over 14 days and under two (2) years of age, not occupying a seat, may be carried free of charge when traveling with an adult (12 years of age or older). Learn more.


Pet Policy

Customers flying with a pet are subject to a pet fare. To learn more about traveling with your furry friend, explore the Southwest Pet Policy.


Unaccompanied Minor

Minors under the age of 18 are not permitted to fly unaccompanied on international flights or any itinerary that includes an international flight. Learn more.


Bags Fly Free1

Start packing! Every ticketed Customer’s first two checked bags are free. Learn more.


The Southwest Travel Experience

At Southwest, we understand that a memorable trip from Denver to Chicago (Midway) contains more than cheap fares from Denver International Airport to Chicago Midway International Airport. That's why Southwest travelers have access to other services and perks, from booking to boarding, that make for smooth travel and set the stage for fun. Find out more about the Southwest Experience, and book your Denver to Chicago (Midway) flight.

It's simple and fun to fly with Southwest, whether for business or pleasure, to any of our myriad locations. When you search for your flight from Denver to Chicago (Midway), you'll find low fares without hidden fees—that's our Transfarency® promise. Stay up to date on our deals by enrolling in the Click 'N Save® emails. Looking for tours, activities, and more hidden gems? Check out Southwest Airlines® Experiences and earn Rapid Rewards® when you book.

1First and second checked bags. Weight and size limits apply.

2Fare difference may apply.