Southwest® flights from Chicago (Midway) to Colorado Springs from $83
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Low fares from Chicago (Midway) to Colorado Springs
$
Chicago (Midway) (MDW)to
Colorado Springs (COS)
Depart: 01/21/2026
One-way
Basic
From
$83
Seen: 7 hrs ago
Chicago (Midway) (MDW)to
Colorado Springs (COS)
Depart: 02/18/2026
One-way
Basic
From
$83
Seen: 3 hrs ago
Chicago (Midway) (MDW)to
Colorado Springs (COS)
Depart: 02/21/2026
One-way
Basic
From
$83
Seen: 8 hrs ago
Chicago (Midway) (MDW)to
Colorado Springs (COS)
Depart: 02/11/2026
One-way
Basic
From
$83
Seen: 5 hrs ago
Chicago (Midway) (MDW)to
Colorado Springs (COS)
Depart: 01/06/2026
One-way
Basic
From
$88
Seen: 8 hrs ago
Chicago (Midway) (MDW)to
Colorado Springs (COS)
Depart: 02/21/2026
One-way
Choice
From
$100
Seen: 8 hrs ago
Explore flights from Chicago (Midway) to Colorado Springs
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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:
Chicago Midway International Airport
Arriving at:
City of Colorado Springs Municipal Airport
Average flight time:
2 hours 34 minutes
Distance:
917 miles
Route Information
150† Weekly flights
- 1‡ Nonstop flight per day Monday through Friday
- 1‡ Nonstop flight on Saturday
- 1‡ Nonstop flight 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 Colorado Springs
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.
Questions we hear the most
The average flight time from Chicago (Midway) to Colorado Springs is 2 hours 34 minutes.
There are 150 weekly flights from Chicago (Midway) to Colorado Springs on Southwest Airlines.
Yes, Southwest flies nonstop from Chicago (Midway) to Colorado Springs once per day from Monday through Friday.
Yes, Southwest flies nonstop from Chicago (Midway) to Colorado Springs once per day on Saturdays and Sundays.
To find the lowest fares by day and time to fly Chicago (Midway) to Colorado Springs with Southwest, check out our Low Fare Calendar.
You can rent a car at City of Colorado Springs Municipal 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.
Check out the Southwest Airlines® Help Center for answers about everything Southwest.
Explore Flights from Other Popular Origins
Popular Flights from Chicago (Midway)
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.