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Find your next flight from Colorado Springs to Chicago (Midway) now!
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Colorado Springs, CO to Chicago (Midway), IL
*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 32 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.
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Find low faresTravel tips for your next Southwest flight
How to board the plane earlier:
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.
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.
Take advantage of free same-day standby9.
Have a change of travel plans? We offer free same-day standby for most fare types: Wanna Get Away Plus®, Anytime and Business Select®. 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!
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| Fare | Fly one-way from $109 (departing on 8/7)* |
|---|---|
| Departing from | Colorado Springs Airport (COS) |
| Arriving at | Chicago Midway International Airport (MDW) |
| Average flight time | 2 hours 22 minutes |
| Distance | 917 miles |
| 156† | Weekly flights |
|---|---|
| 2‡ | Nonstop flights per day Monday through Friday |
| 1 ‡ | Nonstop flight on Saturday |
| 1 ‡ | Nonstop flight on Sunday |
Other popular flights from Colorado Springs:
†Weekly flights based on DOT published scheduled average flights Monday through Sunday between 7/1/2025 and 7/31/2025. Note: route may not operate every day of the week.
‡Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 7/1/2025 and 7/31/2025.
Explore Chicago.
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.
During your visit, make sure you get a taste of the range of cuisines the Windy City has on the menu. For classic Chicago flavors, order up an all-beef hot dog covered in veggies—but never ketchup—or a thin crust, tavern cut Chicago-style pizza. Visit Restaurant Row on Randolph Street in the West Loop to indulge in a Michelin-starred meal at restaurants helmed by celebrity chefs. Outside of the downtown area, the city has several thriving immigrant communities that each boast eclectic eateries—you’ll find something to tempt every eater’s tastebuds.
Questions we hear the most
The average flight time from Colorado Springs to Chicago (Midway) is 2 hours 22 minutes.
There are 156 weekly flights from Colorado Springs to Chicago (Midway) on Southwest Airlines.
Yes, Southwest flies nonstop from Colorado Springs to Chicago (Midway) 2 times 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.
Check the status of your upcoming Southwest flight.
Visit the Southwest Airlines® Help Center for helpful information and answers to frequently asked questions.
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.