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

View $109 flight on Sat, Aug 23, 2025Opens in a new window

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

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

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 27 - Wed, Sep 3
COS
Colorado Springs
MDW
Chicago
$217 Roundtrip, found 12 hours ago
$217
Roundtrip
found 12 hours ago
Select Southwest Airlines flight, departing Wed, Aug 27 from Colorado Springs to Chicago, returning Wed, Sep 3, priced at $217 found 12 hours ago
Southwest Airlines
Wed, Aug 20 - Mon, Aug 25
COS
Colorado Springs
MDW
Chicago
$223 Roundtrip, found 6 hours ago
$223
Roundtrip
found 6 hours ago
Select Southwest Airlines flight, departing Wed, Aug 20 from Colorado Springs to Chicago, returning Mon, Aug 25, priced at $223 found 6 hours ago
Southwest Airlines
Wed, Aug 27 - Wed, Sep 3
COS
Colorado Springs
MDW
Chicago
$227 Roundtrip, found 12 hours ago
$227
Roundtrip
found 12 hours ago
Select Southwest Airlines flight, departing Wed, Aug 27 from Colorado Springs to Chicago, returning Wed, Sep 3, priced at $227 found 12 hours ago
Delta
Sat, Sep 6 - Sat, Sep 13
COS
Colorado Springs
MDW
Chicago
$228 Roundtrip, found 2 days ago
$228
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Sep 6 from Colorado Springs to Chicago, returning Sat, Sep 13, priced at $228 found 2 days ago
Southwest Airlines
Thu, Sep 18 - Mon, Sep 22
COS
Colorado Springs
MDW
Chicago
$229 Roundtrip, found 16 hours ago
$229
Roundtrip
found 16 hours ago
Select Southwest Airlines flight, departing Thu, Sep 18 from Colorado Springs to Chicago, returning Mon, Sep 22, priced at $229 found 16 hours ago
Southwest Airlines
Wed, Aug 27 - Wed, Sep 3
COS
Colorado Springs
MDW
Chicago
$232 Roundtrip, found 12 hours ago
$232
Roundtrip
found 12 hours ago
Select Southwest Airlines flight, departing Wed, Aug 27 from Colorado Springs to Chicago, returning Wed, Sep 3, priced at $232 found 12 hours ago
Southwest Airlines
Wed, Aug 20 - Mon, Aug 25
COS
Colorado Springs
MDW
Chicago
$233 Roundtrip, found 6 hours ago
$233
Roundtrip
found 6 hours ago
Select Southwest Airlines flight, departing Wed, Aug 20 from Colorado Springs to Chicago, returning Mon, Aug 25, priced at $233 found 6 hours ago
Delta
Tue, Nov 11 - Tue, Nov 18
COS
Colorado Springs
MDW
Chicago
$237 Roundtrip, found 1 day ago
$237
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Nov 11 from Colorado Springs to Chicago, returning Tue, Nov 18, priced at $237 found 1 day ago
Southwest Airlines
Thu, Sep 11 - Tue, Sep 16
COS
Colorado Springs
MDW
Chicago
$238 Roundtrip, found 21 hours ago
$238
Roundtrip
found 21 hours ago
Select Southwest Airlines flight, departing Thu, Sep 11 from Colorado Springs to Chicago, returning Tue, Sep 16, priced at $238 found 21 hours ago
Southwest Airlines
Mon, Aug 25 - Tue, Aug 26
COS
Colorado Springs
MDW
Chicago
$239 Roundtrip, found 2 hours ago
$239
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Mon, Aug 25 from Colorado Springs to Chicago, returning Tue, Aug 26, priced at $239 found 2 hours ago

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

August is typically the cheapest month to fly

From $170 - $883 per traveler.

Graph displaying average flight prices per month

Alternative airports near Chicago

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

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $295
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $295
Flights from Colorado Springs (COS) to Chicago (MDW)
Origin airport
Colorado Springs
Destination airport
Midway Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$217
Distance
915 mi
Average flight time
3 hours 22 mins

Colorado Springs to Chicago Flights

The cheapest times to fly from Colorado Springs to Chicago

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 Colorado Springs to Chicago are during the month of August. You can find some of the cheapest flights from Colorado Springs to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Colorado Springs to Chicago

Sunday is one of the best days to book for cheap flights from Colorado Springs to Chicago: 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 Colorado Springs to Chicago

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 Colorado Springs to Chicago 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 Colorado Springs to Chicago 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 Colorado Springs to Chicago 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 Colorado Springs Airport (COS) to Midway Intl. Airport (MDW) cost?
Book cheap return fares starting at $217 from Colorado Springs Airport (COS) to Midway Intl. Airport (MDW). 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 COS on August 14 2025 and touching down at MDW. The price was last updated on July 23 2025 and has not changed since.
What is the cheapest month to fly from COS to MDW?
The cheapest flights from COS to MDW 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 Colorado Springs Airport (COS) to Midway Intl. Airport (MDW)?
Board a direct flight with Southwest Airlines and fly straight from Colorado Springs Airport (COS) to Midway Intl. Airport (MDW).
What is the cheapest airline that flies from COS to MDW?
With prices starting from $109 for a one-way journey from COS to MDW, Southwest Airlines is currently the cheapest carrier operating this route. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from COS on August 23 2025. Prices were last updated on July 23 2025 and have not changed since.
How many flights per day from Colorado Springs Airport (COS) to Midway Intl. Airport (MDW)?
On average, you can choose from 6 direct flights every week from Colorado Springs Airport (COS) to Midway Intl. Airport (MDW). For more flexibility, consider taking a flight with a layover. Enter your dates on Expedia and then filter your search to include one or more stops.
What are the most popular departure times for flights from Colorado Springs Airport (COS) to Midway Intl. Airport (MDW)?
The 11 AM departures from COS to MDW are the top choice for many travelers. These flights can come with a higher price due to their popularity. If you want to save money, book during off-peak hours.
What day of the week has the most flights from COS to MDW?
Travel on a Friday if you're after the largest selection of flights from Colorado Springs Airport (COS) to Midway Intl. Airport (MDW).
What is the earliest flight from Colorado Springs Airport (COS) to Midway Intl. Airport (MDW)?
Colorado Springs Airport (COS)'s first flight to Midway Intl. Airport (MDW) is at approximately 11:50AM UTC-7. With a travel time of 2h 15m, you'll arrive at around 3:05PM UTC-6.
How long does it take to fly from Colorado Springs Airport (COS) to Midway Intl. Airport (MDW)?
Flights from COS to MDW have an average travel time of 2 hours and 17 minutes. The distance between the two is 920 mi.
What airline has the least delays from COS to MDW?
Southwest Airlines has the best track record for on-time direct flights from Colorado Springs Airport (COS) to Midway Intl. Airport (MDW), with an on-time score of 81%. Use the Expedia App to view your flight status before you jet off and get real-time updates about any trip changes.
What is the best time to fly from Colorado Springs Airport (COS) to Midway Intl. Airport (MDW)?
To land at Midway Intl. Airport (MDW) on schedule, choose a flight that leaves from Colorado Springs Airport (COS) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this hour.**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 Chicago from Colorado Springs Airport (COS)?
If you're catching a direct flight from Colorado Springs Airport (COS) to Chicago, you can touch down at either O'Hare Intl. Airport (ORD) or Midway Intl. Airport (MDW).
Is it cheaper to buy a plane ticket from Colorado Springs Airport (COS) to Midway Intl. Airport (MDW) last-minute?
Booking your plane ticket from COS to MDW shortly before your getaway is usually more expensive. However, if you're flexible with your departure dates and times, you could score a cheap last-minute fare.
Is it cheaper to book a COS to MDW flight and hotel package?
Compared with arranging hotels and flights separately, booking a COS to MDW flight and hotel package with Expedia could lead to significant savings. Better still, having everything in one easy place will take the stress out of planning your trip. Simply pick your flights and choose from our extensive range of stays, then personalize your trip with extras like activities, tours and car rentals.
Can I cancel or change the date of my flight from Colorado Springs Airport (COS) to Midway Intl. Airport (MDW)?
In most cases, you can reschedule or cancel your COS to MDW flight. However, additional charges may apply, especially if you booked over 24 hours ago. Check your itinerary for the airline's guidelines and fees on flight changes, or if you want further information, head to our Customer Service portal.

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