Popular airlines from Chicago Midway Airport (MDW) to Colorado Springs Airport (COS)
Southwest AirlinesSouthwest Airlines
DeltaDelta
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Today's featured flight deals from Chicago Midway Airport (MDW) to Colorado Springs Airport (COS)
- Chicago (MDW) to Colorado Springs (COS).Southwest Airlines, nonstop.Departing on Fri, Oct 24 at 12:00pm from Chicago, arriving at 1:35pm in Colorado Springs.Returning on Mon, Oct 27 at 5:20pm from Colorado Springs, arriving on Tue, Oct 28 at 12:05am in Chicago.Select Southwest Airlines flight departing on Fri, Oct 24 at 12:00pm from Chicago, returning on Mon, Oct 27 at 5:20pm from Colorado Springs priced at $18975% less than typical$189
- Chicago (MDW) to Colorado Springs (COS).Southwest Airlines, nonstop.Departing on Mon, Oct 6 at 12:00pm from Chicago, arriving at 1:35pm in Colorado Springs.Returning on Sat, Oct 11 at 3:50pm from Colorado Springs, arriving at 11:05pm in Chicago.Select Southwest Airlines flight departing on Mon, Oct 6 at 12:00pm from Chicago, returning on Sat, Oct 11 at 3:50pm from Colorado Springs priced at $32060% less than typical$320
- Chicago (MDW) to Colorado Springs (COS).Southwest Airlines, nonstop.Departing on Sat, Oct 25 at 6:00pm from Chicago, arriving at 7:35pm in Colorado Springs.Returning on Wed, Oct 29 at 5:30am from Colorado Springs, arriving at 12:40pm in Chicago.Select Southwest Airlines flight departing on Sat, Oct 25 at 6:00pm from Chicago, returning on Wed, Oct 29 at 5:30am from Colorado Springs priced at $21970% less than typical$219
- Chicago (MDW) to Colorado Springs (COS).Southwest Airlines, nonstop.Departing on Sun, Oct 26 at 10:25am from Chicago, arriving at 12:00pm in Colorado Springs.Returning on Wed, Oct 29 at 5:30pm from Colorado Springs, arriving at 10:40pm in Chicago.Select Southwest Airlines flight departing on Sun, Oct 26 at 10:25am from Chicago, returning on Wed, Oct 29 at 5:30pm from Colorado Springs priced at $31360% less than typical$313
- Chicago (MDW) to Colorado Springs (COS).Southwest Airlines, nonstop.Departing on Sat, Sep 27 at 5:35pm from Chicago, arriving at 7:05pm in Colorado Springs.Returning on Wed, Oct 1 at 12:21pm from Colorado Springs, arriving at 4:06pm in Chicago.Select Southwest Airlines flight departing on Sat, Sep 27 at 5:35pm from Chicago, returning on Wed, Oct 1 at 12:21pm from Colorado Springs priced at $43640% less than typical$436
Cheap Flights from Chicago to Colorado Springs (MDW-COS)
Prices were available within the past 7 days and start at $79 for one-way flights and $177 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Find the cheapest month to fly from Chicago (MDW) to Colorado Springs (COS)
September is typically the cheapest month to fly
Frequently asked questions
Travel information
Travel information
Origin airport | Midway Intl. |
Destination airport | Colorado Springs |
Airlines serving | Delta, Southwest Airlines |
Roundtrip price | $176 |
Distance | 915 mi |
Average flight time | 2 hours 25 mins |
Book with confidence
Book with confidence
Chicago to Colorado Springs Flights
The cheapest times to fly from Chicago to Colorado Springs
On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Colorado Springs are during the month of November. You can find some of the cheapest flights from Chicago to Colorado Springs with Expedia's search tool and vast selection of airlines.
The best time to book a flight from Chicago to Colorado Springs
Sunday is one of the best days to book for cheap flights from Chicago to Colorado Springs: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.
How to find cheap round-trip tickets from Chicago to Colorado Springs
Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Colorado Springs in 2025. You can also book with separate airlines for your outbound and return journeys, from $79 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.
Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Colorado Springs flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.
You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Colorado Springs airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.
*Terms apply.
Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.
Explore a world of travel with Expedia
Explore a world of travel with Expedia
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