Southwest® flights from Colorado Springs to Chicago (Midway) from $83
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Low fares from Colorado Springs to Chicago (Midway)
$
Colorado Springs (COS)to
Chicago (Midway) (MDW)
Depart: 02/25/2026
One-way
Basic
From
$83
Seen: 49 minutes ago
Colorado Springs (COS)to
Chicago (Midway) (MDW)
Depart: 02/21/2026
One-way
Basic
From
$83
Seen: 1 hour ago
Colorado Springs (COS)to
Chicago (Midway) (MDW)
Depart: 01/10/2026
One-way
Basic
From
$83
Seen: 45 minutes ago
Colorado Springs (COS)to
Chicago (Midway) (MDW)
Depart: 01/17/2026
One-way
Basic
From
$83
Seen: 23 minutes ago
Colorado Springs (COS)to
Chicago (Midway) (MDW)
Depart: 01/07/2026
One-way
Basic
From
$83
Seen: 3 hrs ago
Colorado Springs (COS)to
Chicago (Midway) (MDW)
Depart: 01/14/2026
One-way
Basic
From
$83
Seen: 2 hrs ago
Explore flights from Colorado Springs to Chicago (Midway)
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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:
City of Colorado Springs Municipal Airport
Arriving at:
Chicago Midway International Airport
Average flight time:
2 hours 21 minutes
Distance:
917 miles
Route Information
151† 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 Chicago (Midway)
When you touch down at Chicago Midway International Airport, you’ll find yourself on the southwest edge of the city and just a short Orange Line ‘L’ ride away from the center of the hustle and bustle—the Loop. What Chicago calls its downtown area, the Loop and its surrounding neighborhoods are home to colleges, theatres, museums, world-class shopping, and Michelin-starred restaurants. Where to begin? Whether you choose to ride the “L” or rent a car, there’s plenty for everyone to explore in the Loop and among the city’s 77 distinct neighborhoods.
If you choose to explore the Loop and the lakefront, consider seeing everything the Museum Campus has to offer. Inside sprawling lakefront Grant Park, the campus is home to five of Chicago’s most beloved attractions, including the Adler Planetarium, the Shedd Aquarium, and the Field Museum of Natural History. Originally called the Columbian Museum of Chicago and established for the 1983 World’s Columbian Exposition, the Field Museum is home to Sue, the largest and most complete Tyrannosaurus rex skeleton so far discovered. If you prefer the stars to terra firma, the Adler Planetarium offers visitors the chance to explore several space science exhibitions year-round.
Questions we hear the most
The average flight time from Colorado Springs to Chicago (Midway) is 2 hours 21 minutes.
There are 151 weekly flights from Colorado Springs to Chicago (Midway) on Southwest Airlines.
Yes, Southwest flies nonstop from Colorado Springs to Chicago (Midway) once per day from Monday through Friday.
Yes, Southwest flies nonstop from Colorado Springs to Chicago (Midway) once per day on Saturdays and Sundays.
To find the lowest fares by day and time to fly Colorado Springs to Chicago (Midway) with Southwest, check out our Low Fare Calendar.
You can rent a car at Chicago Midway International Airport book yours with your flight.
Yes! Flights from Colorado Springs to Chicago (Midway)—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 Colorado Springs
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.