Whether you're traveling for business or pleasure, solo, or with the whole family, you'll enjoy the flexibility of flying Southwest®.
Find your next flight from Chicago (Midway) to Colorado Springs now!
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Whether you're traveling for business or pleasure, solo, or with the whole family, you'll enjoy the flexibility of flying Southwest®.
Find your next flight from Chicago (Midway) to Colorado Springs now!
Chicago (Midway), IL to Colorado Springs, CO
*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 15 travel days available. Fares are updated hourly. Fares displayed on external channels may no longer be available at time of booking. To find the most updated fare, please visit Southwest.com.
Southwest seats are first come, first served based on check-in order. But there are ways to board the plane earlier!
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.
Have a change of travel plans? We offer free same-day standby for all fare types. This means that you can retain your current flight while listing for standby on an earlier flight. If a seat becomes available, it’s yours at no charge!
Rapid Rewards Members can redeem their points for flights, hotel stays, rental cars, gift cards, and more. And your points never expire!
| Fare | Fly one-way from $128 (departing on 4/14)* |
|---|---|
| Departing from | Chicago Midway International Airport (MDW) |
| Arriving at | Colorado Springs Airport (COS) |
| Average flight time | 2 hours 38 minutes |
| Distance | 917 miles |
| 124† | Weekly flights |
|---|---|
| 1‡ | Nonstop flight per day Monday through Friday |
| 1 ‡ | Nonstop flight on Saturday |
| 1 ‡ | Nonstop flight on Sunday |
Other popular flights from Chicago (Midway):
†Weekly flights based on DOT published scheduled average flights Monday through Sunday between 3/1/2025 and 3/31/2025. Note: route may not operate every day of the week.
‡Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 3/1/2025 and 3/31/2025.
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.
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.
4Where available. Available only on WiFi-enabled aircraft. Limited-time offer.
5Due to licensing restrictions, on WiFi-enabled international flights, free live TV and iHeartRadio may not be available for the full duration of flight.
6Texting only allows access to iMessage and WhatsApp (which must be downloaded and activated before connecting to SouthwestWiFi).
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.
8Flights 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.
9Free same-day standby: You can list for same-day standby for an earlier flight via a Southwest Customer Service Agent at the airport or the Southwest app or mobile web. You must request to be added to the same-day standby list at least 10 minutes prior to the scheduled departure of your original flight or the no-show policy will apply. If using the app or mobile web, you must list your name 30 minutes ahead of scheduled departure. You will receive a message based on the contact preference selected during booking if you are cleared on the flight. Group bookings and Unaccompanied Minors are not eligible for same-day standby. You will be required to pay any government taxes and fees associated with these itinerary changes but refunds will be provided. Your original boarding position is not guaranteed on your standby flight. Southwest Business Customers booked through travel agencies may need to see a Southwest agent at the airport for a standby listing. See Southwest.com/standby for more details.