Wing your way from the Windy City to the Springs. Trade big city hustle and bustle for mountain town rest and relaxation with a flight on Southwest Airlines. Southwest flies from Chicago Midway International Airport to Colorado Springs Airport, making it easier to plan your next 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®.
Pack your bags and get ready for your trip from Midway to Colorado Springs.
Chicago (Midway), IL to Colorado Springs, CO
departing on 5/3
one-way starting at*$104
*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 15 travel days available.
|Departing from||Chicago Midway International Airport (MDW)|
|Arriving at||Colorado Springs Airport (COS)|
|Average flight time||2 hours 34 minutes|
|1‡||Nonstop flight per day Monday through Friday|
|1‡||Nonstop flight on Saturday|
|1‡||Nonstop flight on Sunday|
Other popular flights from Chicago (Midway):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.
Your exploration of Colorado Springs can begin as soon as you deplane at Colorado Springs Airport. Next door at the Peterson Airforce Base is the Peterson Air & Space Museum, housed in the airport’s original Art Deco terminal building. Here you can learn about the base’s importance during World War II and explore several aircraft on display.
Whether you hop on a Mountain Metro Transit bus or rent a car, you’ll find yourself in downtown Colorado Springs in no time. While a rental car can help you explore the surrounding area and outer reaches of this largest-by-area city in Colorado, the central-most portions of the city are highly walkable. If you’d prefer to trade your walking shoes for hiking boots, there are three significant trails to take advantage of: the New Santa Fe Regional Trail, the Fountain Creek Regional Trail, and the Pikes Peak Greenway. These three trails form a path from the town of Palmer Lake, through Colorado Springs, and on to the town of Fountain.
With its location at the base of Pikes Peak, it’s no wonder that nature lovers and mountaineers alike find their way to Colorado Springs. If you’d like to summit the mountain but don’t care to hike or drive, you can take a ride on the Manitou and Pikes Peak Cog Railway—the highest cog railroad in the world. Departing from nearby Manitou Springs, this ride allows visitors to fully enjoy all the sights of summitting the mountain with convenience and safety.
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 Colorado Springs 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 Chicago (Midway) to Colorado Springs the best it can be. Learn more about the Southwest® travel experience before you book your flight from Chicago Midway International Airport to Colorado Springs 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 Colorado Springs, 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.