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Cheap flights from Chicago Midway Airport to Colorado Springs from $122

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 9/1. 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
10:15 am - 3:35 pm
MDW
-
COS
6h 20m
2 stops
Southwest Logo
6:15 am - 3:20 pm
COS
-
MDW
8h 05m
1 stop
$277Southwest
Sat, Sep 5 - Wed, Sep 9
Southwest Logo
9:50 am - 6:00 pm
MDW
-
COS
9h 10m
2 stops
Southwest Logo
12:15 pm - 7:15 pm
COS
-
MDW
6h 00m
1 stop
$277Southwest
Sat, Sep 5 - Sat, Sep 19
Delta Logo
1:25 pm - 9:38 pm
MDW
-
COS
9h 13m
2 stops
Delta Logo
1:20 pm - 10:36 pm
COS
-
MDW
8h 16m
1 stop
$277Delta
Sat, Aug 29 - Sat, Sep 5
Southwest Logo
10:05 am - 6:05 pm
MDW
-
COS
9h 00m
2 stops
Southwest Logo
2:00 pm - 10:20 pm
COS
-
MDW
7h 20m
1 stop
$277Southwest
Mon, Aug 24 - Sat, Sep 5
Southwest Logo
6:35 am - 4:45 pm
MDW
-
COS
11h 10m
2 stops
Southwest Logo
11:45 am - 8:40 pm
COS
-
MDW
7h 55m
2 stops
$279Southwest
Sat, Oct 17 - Wed, Oct 21
Delta Logo
12:45 pm - 8:16 pm
MDW
-
COS
8h 31m
1 stop
Delta Logo
1:26 pm - 10:33 pm
COS
-
MDW
8h 07m
1 stop
$281Delta
Tue, Oct 6 - Sat, Oct 10
Delta Logo
4:39 pm - 9:38 pm
MDW
-
COS
5h 59m
1 stop
Delta Logo
1:20 pm - 10:36 pm
COS
-
MDW
8h 16m
1 stop
$281Delta
Sat, Aug 22 - Wed, Aug 26
Delta Logo
1:00 pm - 7:56 pm
MDW
-
COS
7h 56m
1 stop
Delta Logo
1:25 pm - 10:44 pm
COS
-
MDW
8h 19m
1 stop
$281Delta
Tue, Sep 15 - Wed, Sep 16
Delta Logo
6:05 am - 12:15 pm
MDW
-
COS
7h 10m
1 stop
Delta Logo
1:20 pm - 10:36 pm
COS
-
MDW
8h 16m
1 stop
$281Delta
Tue, Aug 25 - Tue, Sep 1
Delta Logo
6:05 am - 12:14 pm
MDW
-
COS
7h 09m
1 stop
Delta Logo
1:26 pm - 10:33 pm
COS
-
MDW
8h 07m
1 stop
$281Delta
Sat, Oct 3 - Sat, Oct 10

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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 5
MDW9:50 amChicago Midway
9h 10m
2 stops
COS6:00 pmColorado Springs
Sep 19
COS12:15 pmColorado Springs
6h 00m
1 stop
MDW7:15 pmChicago Midway
$277
Southwest
Oct 17
MDW6:35 amChicago Midway
11h 10m
2 stops
COS4:45 pmColorado Springs
Oct 21
COS11:45 amColorado Springs
7h 55m
2 stops
MDW8:40 pmChicago Midway
$279
Southwest
Sep 14
MDW4:25 pmChicago Midway
6h 25m
1 stop
COS9:50 pmColorado Springs
Sep 21
COS4:20 pmColorado Springs
4h 45m
1 stop
MDW10:05 pmChicago Midway
$281

Delta flights from Chicago Midway Airport to Colorado Springs

Our best Delta deals on Chicago Midway Airport to Colorado Springs flight tickets
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
$286
Delta
Aug 25
MDW9:24 amChicago Midway
13h 14m
2 stops
COS9:38 pmColorado Springs
Sep 1
COS6:00 amColorado Springs
9h 59m
2 stops
MDW4:59 pmChicago Midway
$292
Delta
Aug 22
MDW4:39 pmChicago Midway
5h 59m
1 stop
COS9:38 pmColorado Springs
Aug 28
COS1:20 pmColorado Springs
8h 16m
1 stop
MDW10:36 pmChicago Midway
$306

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 3, 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 - COS

MDWCOS

Chicago Midway

Sat 9/5

10:15 am-3:35 pm

2 stops6h 20m

Colorado Springs

Wed 9/9

6:15 am-3:20 pm

1 stop8h 05m

$277

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

Sat 9/5

9:50 am-6:00 pm

2 stops9h 10m

Colorado Springs

Sat 9/19

12:15 pm-7:15 pm

1 stop6h 00m

$277

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

Sat 8/29

1:25 pm-9:38 pm

2 stops9h 13m

Colorado Springs

Sat 9/5

1:20 pm-10:36 pm

1 stop8h 16m

$277

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

Mon 8/24

10:05 am-6:05 pm

2 stops9h 00m

Colorado Springs

Sat 9/5

2:00 pm-10:20 pm

1 stop7h 20m

$277

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

Sat 10/17

6:35 am-4:45 pm

2 stops11h 10m

Colorado Springs

Wed 10/21

11:45 am-8:40 pm

2 stops7h 55m

$279

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

Tue 10/6

12:45 pm-8:16 pm

1 stop8h 31m

Colorado Springs

Sat 10/10

1:26 pm-10:33 pm

1 stop8h 07m

$281
Quickest round-trip

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

Sat 8/22

4:39 pm-9:38 pm

1 stop5h 59m

Colorado Springs

Wed 8/26

1:20 pm-10:36 pm

1 stop8h 16m

$281

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

Tue 9/15

1:00 pm-7:56 pm

1 stop7h 56m

Colorado Springs

Wed 9/16

1:25 pm-10:44 pm

1 stop8h 19m

$281

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

Tue 8/25

6:05 am-12:15 pm

1 stop7h 10m

Colorado Springs

Tue 9/1

1:20 pm-10:36 pm

1 stop8h 16m

$281

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

Sat 10/3

6:05 am-12:14 pm

1 stop7h 09m

Colorado Springs

Sat 10/10

1:26 pm-10:33 pm

1 stop8h 07m

$281

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 $328. 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 36% 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 25m

Direct flights

Mon, Tue, Thu, Fri, Sat and Sun

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 25m
Direct flights go from Chicago Midway Airport to Colorado Springs on Monday, Tuesday, 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

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 25m.

  • 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
4,229 reviews
Search Southwest flights

  • Southwest Flights From Chicago Midway Airport to Colorado Springs

    Southwest flies from Chicago Midway Airport to Colorado Springs around 3 times per week, with 4,229 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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