Get ready to see if Chicago is your kind of town when you book a flight with Southwest Airlines. Southwest flies from Colorado Springs Airport to Chicago Midway International Airport, making it easier to plan your next Windy City getaway. If you have flexible travel dates, explore our Low Fare Calendar to find the most affordable tickets within your travel window. Make the most of your reservation with package deals on flights, hotels, rental cars, and more from Southwest Vacations®.
Get ready to explore the City of the Big Shoulders—book your flight today!
Best Airline in the U.S. and North America & Best Economy Class and Low Cost Airline in North America.
Colorado Springs, CO to Chicago (Midway), IL
*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 15 travel days available.
During the ongoing COVID-19 pandemic, the availability, health and safety procedures, operations, and schedules for local attractions are changing constantly. Please contact attractions directly for hours of operation, potential temperature screenings, and other possible health and safety procedures and restrictions. Visit our COVID-19 Travel Information page for information about potential restrictions on air travel.
Departing from: Colorado Springs Airport (COS)
Arriving at: Chicago Midway International Airport (MDW)
Other popular flights from Colorado Springs
View our interactive mapWhen 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.
One child over 14 days and under two (2) years of age, not occupying a seat, may be carried free of charge when traveling with an adult (12 years of age or older). Learn more.
Customers flying with a pet are subject to a pet fare. To learn more about traveling with your furry friend, explore the Southwest® pet policy.
Minors under the age of 18 are not permitted to fly unaccompanied on international flights or any itinerary that includes an international flight. Learn more.
Start packing! Every ticketed Customer’s first two checked bags are free. Learn more.
Chicago Midway International Airport is a quick 30-minute 'L' ride from downtown Chicago. Get going—adventure awaits.
At Southwest, we know it takes more than great deals on Chicago (Midway) airfares and convenient scheduling options to make your trip memorable. So from booking to boarding, we offer services and features designed to make your travel from Colorado Springs to Chicago (Midway) the best it can be. Learn more about the Southwest® travel experience before you book your flight from Colorado Springs Airport to Chicago Midway International Airport.
Flying with Southwest is simple and fun, no matter which of our dozens of exciting destinations you choose. When you search for your next flight to Chicago (Midway), know that you won’t be surprised at checkout. Low fares and no hidden fees. That's Transfarency®. And as always, two bags fly free®1. Want the latest news, information, and promotional offers from Southwest? Sign up to receive email from us. Looking for tours, activities, and more hidden gems to add to your Chicago (Midway) adventure? Explore getaways with Southwest®. Book your flight today and know that you'll earn Rapid Rewards® points when you fly.
1First and second checked bags. Weight and size limits apply.
2Fare difference may apply.
To find the cheapest 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.
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