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Flights from Chicago (MDW) to Colorado Springs (COS)1
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.
1Colorado Springs service starts 3/11/2021.
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Best Airline in the U.S. and North America & Best Economy Class and Low Cost Airline in North America.
During the ongoing COVID-19 pandemic, the availability, health and safety procedures, operations, and schedules for local attractions are changing constantly. Please contact attractions directly for hours of operation, potential temperature screenings, and other possible health and safety procedures and restrictions. Visit our Coronavirus Travel Information page for information about potential restrictions on air travel.
Flight details
Average flight time: 2 hours 55 minutes
Departing from: Chicago Midway International Airport (MDW)
†Based on DOT published scheduled average flights Monday-Friday between 1/29/2021 and 3/31/2021, as of 2/4/2021.
1Colorado Springs service starts 3/11/2021.
Explore Colorado Springs. Service starts 3/11/2021.
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.
Travel tips
Infancy 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 free®2
Start packing! Every ticketed Customer’s first two checked bags are free. Learn more.
The Southwest® travel experience1
It takes more than getting a deal on a flight to make traveling pleasurable. That’s why Southwest works to make every step of the process of getting to your final destination simple, from booking to boarding. Learn more about what you can expect from the Southwest® Experience before you book your next flight from Chicago Midway International Airport to Colorado Springs Airport.
Book your next flight with confidence, knowing that you won’t have to worry about hidden fees—Southwest offers low fares and, as always, bags fly free. That’s Transfarency.® Want to stay in the know about our latest flight and vacation package deals? Enroll in our Click 'N Save® emails. For more information on tours, activities, and more hidden gems, Check out getaways with Southwest® and earn Rapid Rewards® points when you fly.
1Colorado Springs service starts 3/11/2021.
1Colorado Springs service starts 3/11/2021.
2First and second checked bags. Weight and size limits apply.
3Fare difference may apply.
Questions we hear the most
The average flight time from Chicago (Midway) to Colorado Springs is 2 hours 55 minutes.
There are 12 flights daily from Chicago (Midway) to Colorado Springs on Southwest Airlines.
Southwest flies nonstop from Chicago (Midway) to Colorado Springs 2 times daily.
To find the cheapest day and time to fly Chicago (Midway) to Colorado Springs with Southwest, check out our Low Fare Calendar.
Yes! Flights from Chicago (Midway) to Colorado Springs—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 here.
