Trade Rocky Mountain high for towering skyscrapers with a flight on Southwest. Southwest flies from Denver International Airport to Chicago O’Hare International Airport, making it easier to plan your next Great Lakes getaway. If you have flexible travel dates, explore our Low Fare Calendar to find the most affordable tickets within your travel window. Make the most of your reservation with package deals on flights, hotels, rental cars, and more from Southwest Vacations®.
Get ready to wing your way to the Windy City—book your Southwest flight today!
Denver, CO to Chicago (O'Hare), IL
departing on 4/11
one-way starting at*$99
*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 20 travel days available.
|Departing from||Denver International Airport (DEN)|
|Arriving at||Chicago O'Hare International Airport (ORD)|
|Average flight time||2 hours 26 minutes|
|6‡||Nonstop flights per day Monday through Friday|
|3‡||Nonstop flights on Saturday|
|4‡||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.
Chicagoland is very flat. If you find yourself missing the heights of being back home in the Mile High City, buy a ticket to reach the summit of Willis Tower (or Sears Tower, as Chicagoans still call it). Step out into the glass balconies of the observation deck for panoramic views of the city, the lake, and beyond. It’s not the kind of view you’re used to from summits back home, to be sure, but just as breathtaking.
Sightseeing can be done with feet planted firmly on the ground, of course. Walking tours abound, whether you choose to tour the Loop (what Chicagoans call their downtown) or one of the city’s dozens of neighborhoods. Or take to the water for a riverboat architecture tour or a boat ride along the city’s Lake Michigan waterfront for a unique view of the skyline. The lakefront has plenty to explore while downtown, including Museum Campus, Grant Park, and Millennium Park. Can’t get enough of aquatics? Visit the Shedd Aquarium. Want more sky and less skyline? Explore the Adler Planetarium. Seeking opportunities for snap-worthy selfies? Walk through the public art at Millennium Park.
Hungry for more? Treat yourself to some classic Chicago flavors, starting with a hot dog “dragged through the garden”—piled high with onion, relish, tomato, and more, but never ketchup. Italian beef is a classic cuisine, but not the only example of ethnic flavors brought to the city’s dozens of neighborhoods by its vibrant immigrant communities. From authentic Chinese to succulent soul food and everything in between, there’s something for every eater on the menu.
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.
At Southwest, we know it takes more than great deals on Chicago (O'Hare) 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 (O'Hare) the best it can be. Learn more about the Southwest® travel experience before you book your flight from Denver International Airport to Chicago O'Hare 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 (O'Hare), 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.