Southwest® flights from Denver to Chicago (O'Hare) from $69
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Low fares from Denver to Chicago (O'Hare)
$
Denver (DEN)to
Chicago (Midway) (MDW)
Depart: 02/09/2026
One-way
Basic
From
$59
Seen: 6 minutes ago
Denver (DEN)to
Chicago (Midway) (MDW)
Depart: 02/25/2026
One-way
Basic
From
$64
Seen: 19 minutes ago
Denver (DEN)to
Chicago (Midway) (MDW)
Depart: 02/09/2026
One-way
Choice
From
$76
Seen: 6 minutes ago
Denver (DEN)to
Chicago (Midway) (MDW)
Depart: 02/17/2026
One-way
Basic
From
$78
Seen: 23 hrs ago
Denver (DEN)to
Chicago (Midway) (MDW)
Depart: 02/04/2026
One-way
Basic
From
$78
Seen: 43 minutes ago
Denver (DEN)to
Chicago (Midway) (MDW)
Depart: 02/03/2026
One-way
Basic
From
$78
Seen: 38 minutes ago
Explore flights from Denver to Chicago (O'Hare)
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Travel tips for your next Southwest flight
How to board the plane earlier on open seating flights departing on or before January 26, 2026:
Southwest seats are first come, first served based on check-in order. But there are ways to board the plane earlier!
- Purchase EarlyBird Check-In®1 for automatic check-in and a better boarding position.
- Purchase Upgraded Boarding2 to get an A1-A15 boarding position (depending on availability).
- Purchase a Business Select® fare or upgrade to Business Select to get a guaranteed A1-A15 boarding position.
Enjoy movies, sips, and snacks during your flight.
Take advantage of inflight entertainment with free movies4, free live TV5, free texting6, and $8 inflight Internet7.
We also offer free sodas, coffee, and snacks8—learn more about the inflight food and beverage experience.
Make the most of our Rapid Rewards® Program.
Rapid Rewards Members can redeem their points for flights, hotel stays, rental cars, gift cards, and more. And your points never expire!
Flight Details
Departing from:
Denver International Airport
Arriving at:
O'Hare International Airport
Average flight time:
2 hours 30 minutes
Distance:
888 miles
Route Information
121† Weekly flights
- 3‡ Nonstop flights per day Monday through Friday
- 3‡ Nonstop flights on Saturday
- 3‡ Nonstop flights on Sunday
† Weekly flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025. Note: route may not operate every day of the week.
‡ Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025.
Explore Chicago (O'Hare)
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.
Questions we hear the most
The average flight time from Denver to Chicago (O'Hare) is 2 hours 30 minutes.
There are 121 weekly flights from Denver to Chicago (O'Hare) on Southwest Airlines.
Yes, Southwest flies nonstop from Denver to Chicago (O'Hare) 3 times per day from Monday through Friday.
Yes, Southwest flies nonstop from Denver to Chicago (O'Hare) 3 times per day on Saturdays and Sundays.
To find the lowest fares by day and time to fly Denver to Chicago (O'Hare) with Southwest, check out our Low Fare Calendar.
You can rent a car at O'Hare International Airport book yours with your flight.
Yes! Flights from Denver to Chicago (O'Hare)—or from here or there to anywhere—can be changed with no change fees. Fare difference may apply.
Check the status of your upcoming Southwest flight.
Check out the Southwest Airlines® Help Center for answers about everything Southwest.
Explore Flights from Other Popular Origins
Popular Flights from Denver
1EarlyBird Check-In® pricing starts at $15 one-way, and is subject to availability. Pricing may vary based on the popularity and length of each (one-way) flight. Please see optional travel charges for more details.
2Upgraded boarding prices and benefits are per eligible segment. Flights must be within 24 hours of departure to be eligible for upgraded boarding.
3Where available. Available only on WiFi-enabled aircraft. Limited-time offer.
4Due to licensing restrictions, on WiFi-enabled international flights, free live TV and iHeartRadio may not be available for the full duration of flight.
5Texting only allows access to iMessage and WhatsApp (which must be downloaded and activated before connecting to SouthwestWiFi).
6Internet 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.
7Flights traveling 175 miles or less will have only water available. Complimentary snacks are served on flights over 175 miles. If you’re flying between Hawaii and the continental U.S., you’ll have even more snacks to choose from.