Southwest® flights from Chicago-Midway to Colorado Springs from $139
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Low fares from Chicago-Midway to Colorado Springs
$
Chicago-Midway (MDW)to
Colorado Springs (COS)
Depart: 11/11/2026
One-way
Basic
From
$139
Seen: 13 minutes ago
Chicago-Midway (MDW)to
Colorado Springs (COS)
Depart: 12/19/2026
One-way
Basic
From
$162
Seen: 4 hrs ago
Chicago-Midway (MDW)to
Colorado Springs (COS)
Depart: 11/21/2026
One-way
Basic
From
$162
Seen: 22 hrs ago
Chicago-Midway (MDW)to
Colorado Springs (COS)
Depart: 11/23/2026
One-way
Basic
From
$172
Seen: 9 hrs ago
Chicago-Midway (MDW)to
Colorado Springs (COS)
Depart: 12/18/2026
One-way
Basic
From
$172
Seen: 5 hrs ago
Chicago-Midway (MDW)to
Colorado Springs (COS)
Depart: 12/20/2026
One-way
Basic
From
$177
Seen: 4 hrs ago
Explore flights from Chicago-Midway to Colorado Springs
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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.
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