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.
Best Airline in the U.S. and North America & Best Economy Class and Low Cost Airline in North America.
Chicago (Midway), IL to Colorado Springs, CO
*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 16 travel days available.
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 COVID-19 Travel Information page for information about potential restrictions on air travel.
Departing from: Chicago Midway International Airport (MDW)
Arriving at: Colorado Springs Airport (COS)
Other popular flights from Chicago (Midway)
View our interactive mapYour 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.
Start packing! Every ticketed Customer’s first two checked bags are free. 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. Looking for tours, activities, and more hidden gems to add to your Colorado Springs adventure? Explore getaways with Southwest®. 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.
To find the cheapest day and time to fly Chicago (Midway) to Colorado Springs with Southwest, check out our Low Fare Calendar.
You can rent a car at Colorado Springs Airport—book yours with your flight.
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.
Check out the Southwest Airlines® FAQs for answers about everything Southwest.
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