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 enjoyable travel. If your upcoming trip has flexible dates, search for flights with the Low Fare Calendar to discover the lowest fares on 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!
Denver, CO to Chicago (Midway), IL
departing on 4/21
one-way starting at*$103
*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 16 travel days available.
|Departing from||Denver International Airport (DEN)|
|Arriving at||Chicago Midway International Airport (MDW)|
|Average flight time||2 hours 17 minutes|
|9‡||Nonstop flights per day Monday through Friday|
|5‡||Nonstop flights on Saturday|
|7‡||Nonstop flights on Sunday|
Other popular flights from Denver:View our interactive map
†Weekly flights based on DOT published scheduled average flights Monday through Sunday between 4/1/2023 and 4/30/2023. Note: route may not operate every day of the week.
‡Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 4/1/2023 and 4/30/2023.
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.
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.
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.
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.
Chicago Midway International Airport is a quick 30-minute 'L' ride from downtown Chicago. Get going—adventure awaits.
At Southwest, we know it takes more than great deals on Chicago (Midway) airfares and convenient scheduling options to make your trip memorable. So from booking to boarding, we offer services and features designed to make your travel from Denver to Chicago (Midway) the best it can be. Learn more about the Southwest® travel experience before you book your flight from Denver International Airport to Chicago Midway International Airport.
Flying with Southwest is simple and fun, no matter which of our dozens of exciting destinations you choose. When you search for your next flight to Chicago (Midway), know that you won’t be surprised at checkout. Low fares and no hidden fees. That's Transfarency®. And as always, two bags fly free®1. Want the latest news, information, and promotional offers from Southwest? Sign up to receive email from us. Book your flight today and know that you'll earn Rapid Rewards® points when you fly.
1First and second checked bags. Weight and size limits apply.
2Fare difference may apply.
3Failure to cancel a reservation at least 10 minutes prior to departure may result in forfeited Travel Funds.
4Flight credits unexpired on or created on or after July 28, 2022, do not expire and will show an expiration date until our systems are updated. See full details here.
5Where available. Available only on WiFi-enabled aircraft. Limited-time offer.
6Due to licensing restrictions, on WiFi-enabled international flights, free live TV and iHeartRadio may not be available for the full duration of flight.
7Internet access for $8 per device from takeoff to landing. Price is subject to change. May not be available for the full duration of flight. In order to provide a top-notch Internet experience, we prohibit access to certain high-bandwidth applications and websites. We also prohibit access to certain obscene or offensive content.