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Cheap flights from Chicago Midway Airport to Colorado Springs from $110

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 9/11. 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
1 adult, Economy, 0 bags

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
6:50 am - 10:00 amMDW  Chicago Midway-COS Colorado Springs
4h 10m1 stop Denver Intl
Southwest Logo
12:15 pm - 7:15 pmCOS  Colorado Springs-MDW Chicago Midway
6h 00m1 stop Dallas Love Field
$269Southwest
Sat, Sep 12 - Sat, Sep 19
Southwest Logo
2:40 pm - 8:10 pmMDW  Chicago Midway-COS Colorado Springs
6h 30m1 stop Phoenix Sky Harbor Intl
Southwest Logo
6:15 am - 3:20 pmCOS  Colorado Springs-MDW Chicago Midway
8h 05m1 stop Dallas Love Field
$269Southwest
Sat, Sep 19 - Tue, Sep 22
Southwest Logo
10:05 am - 6:00 pmMDW  Chicago Midway-COS Colorado Springs
8h 55m2 stops Birmingham Dallas Love Field
Southwest Logo
12:15 pm - 7:15 pmCOS  Colorado Springs-MDW Chicago Midway
6h 00m1 stop Dallas Love Field
$274Southwest
Sat, Sep 12 - Sat, Sep 19
Southwest Logo
2:40 pm - 8:10 pmMDW  Chicago Midway-COS Colorado Springs
6h 30m1 stop Phoenix Sky Harbor Intl
Southwest Logo
6:55 am - 5:10 pmCOS  Colorado Springs-MDW Chicago Midway
9h 15m2 stops Phoenix Sky Harbor Intl Oklahoma City Will Rogers World
$275Southwest
Sat, Sep 19 - Tue, Sep 22
Southwest Logo
11:15 am - 12:50 pmMDW  Chicago Midway-COS Colorado Springs
2h 35mnonstop
Southwest Logo
2:05 pm - 5:25 pmCOS  Colorado Springs-MDW Chicago Midway
2h 20mnonstop
$277Southwest
Sat, Oct 17 - Thu, Oct 22
Delta Logo
6:05 am - 12:14 pmMDW  Chicago Midway-COS Colorado Springs
7h 09m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:25 pm - 10:44 pmCOS  Colorado Springs-MDW Chicago Midway
8h 19m1 stop Atlanta Hartsfield-Jackson
$278Delta
Sat, Sep 12 - Tue, Sep 15
Delta Logo
6:05 am - 12:14 pmMDW  Chicago Midway-COS Colorado Springs
7h 09m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:25 pm - 10:44 pmCOS  Colorado Springs-MDW Chicago Midway
8h 19m1 stop Atlanta Hartsfield-Jackson
$278Delta
Sat, Sep 12 - Wed, Sep 16
Delta Logo
6:05 am - 12:14 pmMDW  Chicago Midway-COS Colorado Springs
7h 09m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:25 pm - 10:44 pmCOS  Colorado Springs-MDW Chicago Midway
8h 19m1 stop Atlanta Hartsfield-Jackson
$278Delta
Fri, Sep 11 - Tue, Sep 15
Delta Logo
4:39 pm - 9:38 pmMDW  Chicago Midway-COS Colorado Springs
5h 59m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:20 pm - 10:36 pmCOS  Colorado Springs-MDW Chicago Midway
8h 16m1 stop Atlanta Hartsfield-Jackson
$278Delta
Wed, Sep 2 - Sat, Sep 5
Delta Logo
6:05 am - 12:15 pmMDW  Chicago Midway-COS Colorado Springs
7h 10m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:25 pm - 10:44 pmCOS  Colorado Springs-MDW Chicago Midway
8h 19m1 stop Atlanta Hartsfield-Jackson
$278Delta
Wed, Sep 2 - Wed, Sep 9

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Southwest flights from Chicago Midway Airport to Colorado Springs

Our best Southwest deals on Chicago Midway Airport to Colorado Springs flight tickets
Southwest
Sep 12
MDW6:50 amChicago Midway
4h 10m
1 stop
COS10:00 amColorado Springs
Sep 19
COS12:15 pmColorado Springs
6h 00m
1 stop
MDW7:15 pmChicago Midway
$269
Southwest
Sep 12
MDW10:05 amChicago Midway
8h 55m
2 stops
COS6:00 pmColorado Springs
Sep 19
COS12:15 pmColorado Springs
6h 00m
1 stop
MDW7:15 pmChicago Midway
$274
Southwest
Sep 19
MDW2:40 pmChicago Midway
6h 30m
1 stop
COS8:10 pmColorado Springs
Sep 22
COS6:55 amColorado Springs
9h 15m
2 stops
MDW5:10 pmChicago Midway
$275

Delta flights from Chicago Midway Airport to Colorado Springs

Our best Delta deals on Chicago Midway Airport to Colorado Springs flight tickets
Delta
Sep 2
MDW4:39 pmChicago Midway
5h 59m
1 stop
COS9:38 pmColorado Springs
Sep 5
COS1:20 pmColorado Springs
8h 16m
1 stop
MDW10:36 pmChicago Midway
$278
Delta
Oct 3
MDW9:29 amChicago Midway
11h 27m
2 stops
COS7:56 pmColorado Springs
Oct 10
COS1:26 pmColorado Springs
8h 07m
1 stop
MDW10:33 pmChicago Midway
$279
Delta
Sep 10
MDW6:05 amChicago Midway
7h 09m
1 stop
COS12:14 pmColorado Springs
Sep 12
COS1:25 pmColorado Springs
8h 19m
1 stop
MDW10:44 pmChicago Midway
$282

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 August 16, 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

Cheapest round-trip

ChicagoColorado Springs

MDW Chicago Midway - COS Colorado Springs

MDWCOS

Chicago Midway

Sat 9/12

6:50 am-10:00 am

1 stop4h 10m

Colorado Springs

Sat 9/19

12:15 pm-7:15 pm

1 stop6h 00m

$269

ChicagoColorado Springs

MDW Chicago Midway - COS Colorado Springs

MDWCOS

Chicago Midway

Sat 9/19

2:40 pm-8:10 pm

1 stop6h 30m

Colorado Springs

Tue 9/22

6:15 am-3:20 pm

1 stop8h 05m

$269

ChicagoColorado Springs

MDW Chicago Midway - COS Colorado Springs

MDWCOS

Chicago Midway

Sat 9/12

10:05 am-6:00 pm

2 stops8h 55m

Colorado Springs

Sat 9/19

12:15 pm-7:15 pm

1 stop6h 00m

$274

ChicagoColorado Springs

MDW Chicago Midway - COS Colorado Springs

MDWCOS

Chicago Midway

Sat 9/19

2:40 pm-8:10 pm

1 stop6h 30m

Colorado Springs

Tue 9/22

6:55 am-5:10 pm

2 stops9h 15m

$275
Quickest round-trip

ChicagoColorado Springs

MDW Chicago Midway - COS Colorado Springs

MDWCOS

Chicago Midway

Sat 10/17

11:15 am-12:50 pm

Nonstop2h 35m

Colorado Springs

Thu 10/22

2:05 pm-5:25 pm

Nonstop2h 20m

$277

ChicagoColorado Springs

MDW Chicago Midway - COS Colorado Springs

MDWCOS

Chicago Midway

Sat 9/12

6:05 am-12:14 pm

1 stop7h 09m

Colorado Springs

Tue 9/15

1:25 pm-10:44 pm

1 stop8h 19m

$278

ChicagoColorado Springs

MDW Chicago Midway - COS Colorado Springs

MDWCOS

Chicago Midway

Sat 9/12

6:05 am-12:14 pm

1 stop7h 09m

Colorado Springs

Wed 9/16

1:25 pm-10:44 pm

1 stop8h 19m

$278

ChicagoColorado Springs

MDW Chicago Midway - COS Colorado Springs

MDWCOS

Chicago Midway

Fri 9/11

6:05 am-12:14 pm

1 stop7h 09m

Colorado Springs

Tue 9/15

1:25 pm-10:44 pm

1 stop8h 19m

$278

ChicagoColorado Springs

MDW Chicago Midway - COS Colorado Springs

MDWCOS

Chicago Midway

Wed 9/2

4:39 pm-9:38 pm

1 stop5h 59m

Colorado Springs

Sat 9/5

1:20 pm-10:36 pm

1 stop8h 16m

$278

ChicagoColorado Springs

MDW Chicago Midway - COS Colorado Springs

MDWCOS

Chicago Midway

Wed 9/2

6:05 am-12:15 pm

1 stop7h 10m

Colorado Springs

Wed 9/9

1:25 pm-10:44 pm

1 stop8h 19m

$278

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 month to fly to Colorado Springs?

The month of April is another great option to travel to Colorado Springs, with average flight prices from Chicago Midway Airport averaging around $229.

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 $331. 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 $421.

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

Flying to Colorado Springs from Chicago Midway Airport in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $283 when looking at flights departing in the afternoon. Flights to Colorado Springs are more costly in the evening, with an average ticket price of $392. 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 Airport to Colorado Springs flights?

There is only 1 cabin class available to choose from on Chicago Midway Airport 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 22% 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

Best Price Found

$288

Fastest flight time

2h 30m

Direct flights

Every day

Airports in Colorado Springs

1 airport
The best one-way flight to Colorado Springs from Chicago Midway Airport in the past 72 hours is $288. The best round-trip flight deal from Chicago Midway Airport to Colorado Springs found on momondo in the last 72 hours is $322.
The fastest flight from Chicago Midway Airport to Colorado Springs takes 2h 30m
Direct flights go from Chicago Midway Airport to Colorado Springs every day.
There is 1 airport in Colorado Springs. From Chicago Midway Airport there are direct flights to Colorado Springs (COS).
Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to Colorado Springs

  • 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 $239Free CancellationRating
8.0
4,219 reviews
Search Southwest flights

  • Southwest Flights From Chicago Midway Airport to Colorado Springs

    Southwest flies from Chicago Midway Airport to Colorado Springs around 4 times per week, with 4,219 momondo users rating the airline 8.0/10. The cheapest Southwest deal from Chicago Midway Airport to Colorado Springs in the last 72 hours was $239 (round-trip), much lower than the average airfare cost of $443 for Southwest flights on this route.

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.

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