Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Chicago Midway Airport to Colorado Springs from $95

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Colorado Springs departing on 2/4. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Chicago Midway Airport to Colorado Springs

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
12:25 pm - 4:35 pm
MDW
-
COS
5h 10m1 stop
Southwest Logo
6:50 pm - 5:20 am
COS
-
MDW
9h 30m1 stop
$190Southwest
Tue, Mar 17 - Tue, Mar 24
Southwest Logo
8:10 am - 5:05 pm
MDW
-
COS
9h 55m1 stop
Southwest Logo
5:15 am - 1:00 pm
COS
-
MDW
6h 45m1 stop
$198Southwest
Tue, Feb 10 - Sat, Feb 14
Delta Logo
9:35 am - 8:28 pm
MDW
-
COS
11h 53m2 stops
Delta Logo
1:28 pm - 10:31 pm
COS
-
MDW
8h 03m1 stop
$202Delta
Tue, Mar 17 - Tue, Mar 24
Southwest Logo
10:05 am - 3:55 pm
MDW
-
COS
6h 50m1 stop
Southwest Logo
9:45 am - 5:00 pm
COS
-
MDW
6h 15m2 stops
$203Southwest
Tue, Feb 10 - Sat, Feb 14
Southwest Logo
8:10 am - 3:55 pm
MDW
-
COS
8h 45m2 stops
Southwest Logo
9:45 am - 5:00 pm
COS
-
MDW
6h 15m2 stops
$209Southwest
Tue, Feb 10 - Sat, Feb 14
Southwest Logo
5:20 am - 9:55 am
MDW
-
COS
5h 35m1 stop
Southwest Logo
4:50 pm - 10:25 pm
COS
-
MDW
4h 35m1 stop
$221Southwest
Tue, Feb 17 - Thu, Feb 19
Southwest Logo
2:10 pm - 9:35 pm
MDW
-
COS
8h 25m1 stop
Southwest Logo
6:00 am - 2:45 pm
COS
-
MDW
7h 45m1 stop
$234Southwest
Tue, Jan 20 - Tue, Jan 27
Southwest Logo
8:10 am - 3:40 pm
MDW
-
COS
8h 30m2 stops
Southwest Logo
10:40 am - 7:45 pm
COS
-
MDW
8h 05m2 stops
$235Southwest
Tue, Mar 17 - Tue, Mar 24
Southwest Logo
2:10 pm - 9:35 pm
MDW
-
COS
8h 25m1 stop
Southwest Logo
7:20 am - 4:40 pm
COS
-
MDW
8h 20m2 stops
$239Southwest
Tue, Jan 20 - Tue, Jan 27
Southwest Logo
4:05 pm - 7:30 pm
MDW
-
COS
4h 25m1 stop
Southwest Logo
12:05 pm - 7:55 pm
COS
-
MDW
6h 50m1 stop
$242Southwest
Sat, Jan 31 - Mon, Feb 2

Southwest flights from Chicago Midway Airport to Colorado Springs

Our best Southwest deals on Chicago Midway Airport to Colorado Springs flight tickets
Southwest
Mar 17
MDW12:25 pmChicago Midway
5h 10m
1 stop
COS4:35 pmColorado Springs
Mar 24
COS6:50 pmColorado Springs
9h 30m
1 stop
MDW5:20 amChicago Midway
$190
Find similar
Southwest
Feb 10
MDW8:10 amChicago Midway
9h 55m
1 stop
COS5:05 pmColorado Springs
Feb 14
COS5:15 amColorado Springs
6h 45m
1 stop
MDW1:00 pmChicago Midway
$198
Find similar
Southwest
Feb 10
MDW10:05 amChicago Midway
6h 50m
1 stop
COS3:55 pmColorado Springs
Feb 14
COS9:45 amColorado Springs
6h 15m
2 stops
MDW5:00 pmChicago Midway
$203
Find similar

Delta flights from Chicago Midway Airport to Colorado Springs

Our best Delta deals on Chicago Midway Airport to Colorado Springs flight tickets
Delta
Mar 17
MDW9:35 amChicago Midway
11h 53m
2 stops
COS8:28 pmColorado Springs
Mar 24
COS1:28 pmColorado Springs
8h 03m
1 stop
MDW10:31 pmChicago Midway
$202
Find similar
Delta
Jan 29
MDW6:00 amChicago Midway
7h 23m
1 stop
COS12:23 pmColorado Springs
Feb 1
COS1:20 pmColorado Springs
8h 02m
1 stop
MDW10:22 pmChicago Midway
$249
Find similar
Delta
Jan 20
MDW10:48 amChicago Midway
12h 35m
2 stops
COS10:23 pmColorado Springs
Feb 3
COS7:59 amColorado Springs
9h 37m
2 stops
MDW6:36 pmChicago Midway
$259
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Colorado Springs that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated January 6, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Colorado Springs that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

Tue 3/17

12:25 pm-4:35 pm

1 stop5h 10m

Colorado Springs

Tue 3/24

6:50 pm-5:20 am

1 stop9h 30m

$190

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

Tue 2/10

8:10 am-5:05 pm

1 stop9h 55m

Colorado Springs

Sat 2/14

5:15 am-1:00 pm

1 stop6h 45m

$198

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

Tue 3/17

9:35 am-8:28 pm

2 stops11h 53m

Colorado Springs

Tue 3/24

1:28 pm-10:31 pm

1 stop8h 03m

$202

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

Tue 2/10

10:05 am-3:55 pm

1 stop6h 50m

Colorado Springs

Sat 2/14

9:45 am-5:00 pm

2 stops6h 15m

$203

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

Tue 2/10

8:10 am-3:55 pm

2 stops8h 45m

Colorado Springs

Sat 2/14

9:45 am-5:00 pm

2 stops6h 15m

$209

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

Tue 2/17

5:20 am-9:55 am

1 stop5h 35m

Colorado Springs

Thu 2/19

4:50 pm-10:25 pm

1 stop4h 35m

$221

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

Tue 1/20

2:10 pm-9:35 pm

1 stop8h 25m

Colorado Springs

Tue 1/27

6:00 am-2:45 pm

1 stop7h 45m

$234

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

Tue 3/17

8:10 am-3:40 pm

2 stops8h 30m

Colorado Springs

Tue 3/24

10:40 am-7:45 pm

2 stops8h 05m

$235

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

Tue 1/20

2:10 pm-9:35 pm

1 stop8h 25m

Colorado Springs

Tue 1/27

7:20 am-4:40 pm

2 stops8h 20m

$239

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

Sat 1/31

4:05 pm-7:30 pm

1 stop4h 25m

Colorado Springs

Mon 2/2

12:05 pm-7:55 pm

1 stop6h 50m

$242

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to Colorado Springs from

How to get the cheapest flight ticket from Chicago Midway Airport to Colorado Springs

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Colorado Springs?

The cheapest day to depart from Chicago Midway Airport to Colorado Springs is on a Wednesday when prices can be found for as low as $311. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Chicago Midway Airport to Colorado Springs for around $391.

What is the cheapest time of day to depart on your flight to Colorado Springs?

Flying to Colorado Springs from Chicago Midway Airport at noon is the least expensive time of day to depart. momondo users have found prices as low as $275 when looking at flights departing at noon. Flights to Colorado Springs are more costly in the evening, with an average ticket price of $387. Departure times in the evening fall within the peak daily travel times, which is why tickets can be more expensive.

What is the cheapest Chicago Midway to Colorado Springs flight route?

Fly from Chicago Midway to Colorado Springs for the best Chicago Midway - Colorado Springs flight prices

What cabin class options are available on Chicago Midway to Colorado Springs flights?

There is only 1 cabin class available to choose from on Chicago Midway to Colorado Springs flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago Midway Airport to Colorado Springs flights?

You could potentially save up to 10% on your flight if you consider stops on a Chicago Midway Airport to Colorado Springs flight.

When to book flights from Chicago Midway Airport to Colorado Springs

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Colorado Springs according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to Colorado Springs (MDW to COS) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Colorado Springs

Fastest flight time

2h 30m

Direct flights

Mon, Wed, Thu, Fri, Sat and Sun

Airports in Colorado Springs

1 airport
The fastest flight from Chicago Midway Airport to Colorado Springs takes 2h 30m
Direct flights go from Chicago Midway Airport to Colorado Springs on Monday, Wednesday, Thursday, Friday, Saturday and Sunday. There are no airlines offering direct flights.
There is 1 airport in Colorado Springs. From Chicago Midway Airport there are direct flights to Colorado Springs (COS).
Search flight deals

  • How far is Chicago Midway to Colorado Springs by plane?

    Chicago Midway and Colorado Springs are 920.2 mi apart from one another. By plane, this route typically takes 2h 30m.

  • When did momondo last update prices for flights from Chicago Midway Airport to Colorado Springs Airport?

    Prices for flights from Chicago Midway Airport to Colorado Springs Airport are updated daily.

  • How many operators does momondo search for flights from Chicago Midway Airport to Colorado Springs Airport?

  • How old do you have to be to fly from Chicago Midway Airport to Colorado Springs Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago Midway Airport to Colorado Springs Airport.

  • What documentation or ID do you need to fly to Colorado Springs Airport?

    The travel and health documents you'll need for your trip to Colorado Springs Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Colorado Springs Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Chicago Midway Airport to Colorado Springs?

  • What is the most popular airline from Chicago Midway Airport to Colorado Springs?

Best airlines flying from Chicago Midway Airport to Colorado Springs

Compare and see reviews for airlines that fly from Chicago Midway Airport to Colorado Springs with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $241Free CancellationRating
8.0
4,249 reviews
Search Southwest flights

Traveling to a place near Colorado Springs?

Book flights to Colorado Springs if you plan to visit one of these locations
Cañon City

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Colorado Springs?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Colorado Springs. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Chicago to Colorado Springs with flexible booking policies on momondo?

Yes. All flights to Colorado Springs from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Chicago to Colorado Springs?

Once you have performed a search for Chicago to Colorado Springs flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Chicago to Colorado Springs right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Chicago to Colorado Springs now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Colorado Springs and let you know when they change.

An easier way to manage your Colorado Springs trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Thu 2/5
Thu 2/12
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States