Book low fares from Colorado Springs to Chicago (Midway) with Southwest Airlines®. It’s easy to find the Colorado Springs Airport to Chicago Midway International Airport flight to make your booking and travel a breeze. Whether you’re traveling for business or pleasure, solo or with the whole family, you’ll enjoy flying Southwest®. Have flexible travel dates? Plug them into the Low Fare Calendar and see the lowest fares available within your travel window. You may also want to browse Southwest Vacations® to see special offers and package deals on flights, hotels, rental cars, and more.
Explore your options and book your Colorado Springs to Chicago (Midway) flight with Southwest today!
Best Airline in the U.S. and North America & Best Economy 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. 20 travel days available.
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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 Coronavirus Travel Information page for information about potential restrictions on air travel.
Average flight time: 2 hours 45 minutes
Departing from: Colorado Springs Airport (COS)
Arriving at: Chicago Midway International Airport (MDW)
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Other popular flights from Colorado Springs
View our interactive map†Based on DOT published scheduled average flights Monday-Friday between 3/11/2021 and 4/11/2021, as of 11/2/2020.
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.
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. Find out more about the Southwest® Experience before you book your Colorado Springs Airport to Chicago Midway International Airport flight.
Flying with Southwest is simple and fun, no matter which of our dozens of exciting destinations you choose. And when you search for your next flight to Chicago (Midway), you know you won’t be surprised at checkout. Low fares, no hidden fees. That’s our Transfarency® promise. And, as always, bags fly free. Enroll in our Click 'N Save® emails and stay up to date on our latest flight deals. Looking for tours, activities, and more hidden gems to add to your Chicago (Midway) adventure? Explore Southwest Airlines® Experiences and earn Rapid Rewards® points when you fly.
1First and second checked bags. Weight and size limits apply.
2Fare difference may apply.
How long is the flight from Colorado Springs to Chicago (Midway)?
The average flight time from Colorado Springs to Chicago (Midway) is 2 hours 45 minutes.
How many Southwest flights from Colorado Springs to Chicago (Midway) occur daily?
There are 11 flights daily from Colorado Springs to Chicago (Midway) on Southwest Airlines.
Does Southwest fly nonstop from Colorado Springs to Chicago (Midway)?
Southwest flies nonstop from Colorado Springs to Chicago (Midway) once daily.
What day is it cheapest to fly from Colorado Springs to Chicago (Midway)?
To find the cheapest day and time to fly Colorado Springs to Chicago (Midway) with Southwest, check out our Low Fare Calendar.
Can I rent a car at Chicago Midway International Airport?
You can rent a car at Chicago Midway International Airport—book yours with your flight.
Can I change my flight reservation for my flight from Colorado Springs to Chicago (Midway)?
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.
Where can I find the status of my flight from Colorado Springs to Chicago (Midway)?
Check the status of your upcoming Southwest flight here.
Where can I find answers to other questions about flying from Colorado Springs to Chicago (Midway) with Southwest?
Check out the Southwest Airlines® FAQs for answers about everything Southwest.
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