$109 Cheap Flights from Chicago (MDW) to Colorado Springs (COS)

View $109 flight on Wed, Aug 20, 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Colorado Springs Airport (COS)

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Cheap Flights from Chicago to Colorado Springs (MDW-COS)

Prices were available within the past 7 days and start at $109 for one-way flights and $217 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Wed, Aug 20 - Tue, Aug 26
MDW
Chicago
COS
Colorado Springs
$217 Roundtrip, found 2 hours ago
$217
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Wed, Aug 20 from Chicago to Colorado Springs, returning Tue, Aug 26, priced at $217 found 2 hours ago
Southwest Airlines
Thu, Oct 30 - Sat, Nov 1
MDW
Chicago
COS
Colorado Springs
$223 Roundtrip, found 12 hours ago
$223
Roundtrip
found 12 hours ago
Select Southwest Airlines flight, departing Thu, Oct 30 from Chicago to Colorado Springs, returning Sat, Nov 1, priced at $223 found 12 hours ago
Southwest Airlines
Wed, Aug 20 - Tue, Aug 26
MDW
Chicago
COS
Colorado Springs
$227 Roundtrip, found 2 hours ago
$227
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Wed, Aug 20 from Chicago to Colorado Springs, returning Tue, Aug 26, priced at $227 found 2 hours ago
Southwest Airlines
Wed, Aug 20 - Tue, Aug 26
MDW
Chicago
COS
Colorado Springs
$232 Roundtrip, found 2 hours ago
$232
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Wed, Aug 20 from Chicago to Colorado Springs, returning Tue, Aug 26, priced at $232 found 2 hours ago
Southwest Airlines
Sat, Oct 11 - Tue, Oct 14
MDW
Chicago
COS
Colorado Springs
$233 Roundtrip, found 6 hours ago
$233
Roundtrip
found 6 hours ago
Select Southwest Airlines flight, departing Sat, Oct 11 from Chicago to Colorado Springs, returning Tue, Oct 14, priced at $233 found 6 hours ago
Delta
Tue, Jan 6 - Wed, Jan 21
MDW
Chicago
COS
Colorado Springs
$237 Roundtrip, just found
$237
Roundtrip
just found
Select Delta flight, departing Tue, Jan 6 from Chicago to Colorado Springs, returning Wed, Jan 21, priced at $237 just found
Southwest Airlines
Sat, Oct 11 - Tue, Oct 14
MDW
Chicago
COS
Colorado Springs
$239 Roundtrip, found 6 hours ago
$239
Roundtrip
found 6 hours ago
Select Southwest Airlines flight, departing Sat, Oct 11 from Chicago to Colorado Springs, returning Tue, Oct 14, priced at $239 found 6 hours ago
Southwest Airlines
Sun, Aug 31 - Thu, Sep 4
MDW
Chicago
COS
Colorado Springs
$240 Roundtrip, found 1 day ago
$240
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sun, Aug 31 from Chicago to Colorado Springs, returning Thu, Sep 4, priced at $240 found 1 day ago
Southwest Airlines
Wed, Aug 20 - Tue, Aug 26
MDW
Chicago
COS
Colorado Springs
$242 Roundtrip, found 2 hours ago
$242
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Wed, Aug 20 from Chicago to Colorado Springs, returning Tue, Aug 26, priced at $242 found 2 hours ago
Southwest Airlines
Wed, Nov 5 - Wed, Nov 12
MDW
Chicago
COS
Colorado Springs
$244 Roundtrip, found 7 hours ago
$244
Roundtrip
found 7 hours ago
Select Southwest Airlines flight, departing Wed, Nov 5 from Chicago to Colorado Springs, returning Wed, Nov 12, priced at $244 found 7 hours ago

Find the cheapest month to fly from Chicago (MDW) to Colorado Springs (COS)

September is typically the cheapest month to fly

From $165 - $753 per traveler.

Graph displaying average flight prices per month

Alternative airports near Colorado Springs

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Colorado Springs Airport COS. Cheapest and Closest option available. Average driving time to city center is 16 minutes. Flights from $315
COS
Colorado Springs Airport
CheapestClosest
Average driving time to city center16 min
Flights from $315
Flights from Chicago (MDW) to Colorado Springs (COS)
Origin airport
Midway Intl.
Destination airport
Colorado Springs
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$217
Distance
915 mi
Average flight time
1 hour 31 mins

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 August. 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 $109 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.

 

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Colorado Springs Airport (COS) cost?
You'll find affordable return tickets from Midway Intl. Airport (MDW) to Colorado Springs Airport (COS) starting from $217. Book a seat and start your adventure. This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Southwest Airlines flight leaving MDW on August 15 2025 and touching down at COS. The price was last updated on July 23 2025 and has not changed since.
What is the cheapest month to fly from MDW to COS?
The cheapest flights from MDW to COS are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Midway Intl. Airport (MDW) to Colorado Springs Airport (COS)?
When departing from Midway Intl. Airport (MDW), you can take a direct flight to Colorado Springs Airport (COS) with Southwest Airlines.
What is the cheapest airline that flies from MDW to COS?
With prices starting from $109 for a one-way journey from MDW to COS, Southwest Airlines is currently the cheapest carrier on this route. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from MDW on October 15 2025. Prices were last updated on July 23 2025 and have not changed since.
How many flights per day from Midway Intl. Airport (MDW) to Colorado Springs Airport (COS)?
On average, you can take your pick of 6 nonstop flights departing from Midway Intl. Airport (MDW) to Colorado Springs Airport (COS) every week. If you don't see one that fits your schedule, think about booking a flight with a layover. Customize your search results on Expedia to include one or more stops and choose the next best option.
What are the most popular departure times for flights from Midway Intl. Airport (MDW) to Colorado Springs Airport (COS)?
More people fly between MDW and COS at 12 PM than at any other time. Rather skip the crowds? Consider flying outside peak hours and you could save on your fare as well.
What day of the week has the most flights from MDW to COS?
Travel on a Friday if you're searching for the best choice of flights from Midway Intl. Airport (MDW) to Colorado Springs Airport (COS).
What is the earliest flight from Midway Intl. Airport (MDW) to Colorado Springs Airport (COS)?
Midway Intl. Airport (MDW)'s first flight to Colorado Springs Airport (COS) takes off at approximately 11:35AM UTC-6. With a total flight time of 2h 40m, you'll land at around 1:15PM UTC-7.
How long does it take to fly from Midway Intl. Airport (MDW) to Colorado Springs Airport (COS)?
It takes about 2 hours and 40 minutes to cover the 920 mi from MDW to COS.
What is the best time to fly from Midway Intl. Airport (MDW) to Colorado Springs Airport (COS)?
To avoid possible delays on the Midway Intl. Airport (MDW) to Colorado Springs Airport (COS) route, fly before 3 PM. Flights after this time are 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Colorado Springs from Midway Intl. Airport (MDW)?
Compare your flight options from Midway Intl. Airport (MDW) to Colorado Springs Airport (COS). This is the only Colorado Springs airport you can jet into if you're taking a direct flight.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Colorado Springs Airport (COS) last-minute?
Waiting until just before your trip to book a flight from MDW to COS often results in higher prices. Although you may find some last-minute offers, they're not always guaranteed. Be flexible with your itinerary for a better chance of snagging a bargain.
Is it cheaper to book a MDW to COS flight and hotel package?
You can save money by booking a MDW to COS flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's easy to manage it all in one place. Once you've chosen your ideal accommodations and flights, you can add extras such as activities, tours and car rentals.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Colorado Springs Airport (COS)?
Generally, it's possible to reschedule or cancel your MDW to COS flight. However, for bookings made more than 24 hours ago, additional charges may apply. Check your airline's policies in your itinerary to see what changes are allowed and if any costs are involved. You'll also find further details on our Customer Service portal.

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*Available to One Key members.