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Cheap flights from Chicago Midway Airport to Colorado Springs from $154

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 8/18. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago Midway Airport to Colorado Springs

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
6:05 am - 12:15 pm
MDW
-
COS
7h 10m
1 stop
Delta Logo
1:21 pm - 10:36 pm
COS
-
MDW
8h 15m
1 stop
$322Delta
Thu, Aug 6 - Tue, Aug 11
Delta Logo
6:05 am - 12:15 pm
MDW
-
COS
7h 10m
1 stop
Delta Logo
11:27 am - 10:36 pm
COS
-
MDW
10h 09m
2 stops
$327Delta
Thu, Aug 6 - Tue, Aug 11
Southwest Logo
5:25 am - 8:45 am
MDW
-
COS
4h 20m
1 stop
Southwest Logo
6:10 pm - 12:05 am
COS
-
MDW
4h 55m
1 stop
$339Southwest
Sat, Jun 13 - Tue, Jun 16
Delta Logo
1:18 pm - 10:41 pm
MDW
-
COS
10h 23m
2 stops
Delta Logo
11:10 am - 5:52 pm
COS
-
MDW
5h 42m
1 stop
$342Delta
Thu, Jul 9 - Sat, Jul 11
Southwest Logo
5:25 am - 8:45 am
MDW
-
COS
4h 20m
1 stop
Southwest Logo
1:15 pm - 4:35 pm
COS
-
MDW
2h 20mnonstop
$344Southwest
Sat, Aug 1 - Thu, Aug 13
Southwest Logo
1:00 pm - 8:35 pm
MDW
-
COS
8h 35m
2 stops
Southwest Logo
1:15 pm - 4:35 pm
COS
-
MDW
2h 20mnonstop
$349Southwest
Sat, Aug 1 - Thu, Aug 13
Southwest Logo
3:35 pm - 5:00 pm
MDW
-
COS
2h 25mnonstop
Southwest Logo
10:40 am - 2:00 pm
COS
-
MDW
2h 20mnonstop
$351Southwest
Wed, Aug 19 - Sat, Aug 22
Southwest Logo
1:00 pm - 8:35 pm
MDW
-
COS
8h 35m
2 stops
Southwest Logo
1:30 pm - 8:20 pm
COS
-
MDW
5h 50m
1 stop
$359Southwest
Sat, Aug 1 - Thu, Aug 13
Southwest Logo
5:15 am - 8:55 am
MDW
-
COS
4h 40m
1 stop
Southwest Logo
2:40 pm - 6:00 pm
COS
-
MDW
2h 20mnonstop
$361Southwest
Mon, Jul 6 - Fri, Jul 10
Southwest Logo
5:40 pm - 7:15 pm
MDW
-
COS
2h 35mnonstop
Southwest Logo
6:10 pm - 12:05 am
COS
-
MDW
4h 55m
1 stop
$363Southwest
Sat, Jun 13 - Tue, Jun 16

Southwest flights from Chicago Midway Airport to Colorado Springs

Our best Southwest deals on Chicago Midway Airport to Colorado Springs flight tickets
Southwest
Jun 13
MDW5:25 amChicago Midway
4h 20m
1 stop
COS8:45 amColorado Springs
Jun 16
COS6:10 pmColorado Springs
4h 55m
1 stop
MDW12:05 amChicago Midway
$339
Southwest
Aug 1
MDW5:25 amChicago Midway
4h 20m
1 stop
COS8:45 amColorado Springs
Aug 13
COS1:15 pmColorado Springs
2h 20m
MDW4:35 pmChicago Midway
$344
Southwest
Aug 1
MDW1:00 pmChicago Midway
8h 35m
2 stops
COS8:35 pmColorado Springs
Aug 13
COS1:15 pmColorado Springs
2h 20m
MDW4:35 pmChicago Midway
$349

Delta flights from Chicago Midway Airport to Colorado Springs

Our best Delta deals on Chicago Midway Airport to Colorado Springs flight tickets
Delta
Aug 6
MDW6:05 amChicago Midway
7h 10m
1 stop
COS12:15 pmColorado Springs
Aug 11
COS1:21 pmColorado Springs
8h 15m
1 stop
MDW10:36 pmChicago Midway
$322
Delta
Aug 6
MDW6:05 amChicago Midway
7h 10m
1 stop
COS12:15 pmColorado Springs
Aug 11
COS11:27 amColorado Springs
10h 09m
2 stops
MDW10:36 pmChicago Midway
$327
Delta
Jul 9
MDW1:18 pmChicago Midway
10h 23m
2 stops
COS10:41 pmColorado Springs
Jul 11
COS11:10 amColorado Springs
5h 42m
1 stop
MDW5:52 pmChicago Midway
$342

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 May 24, 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

Thu 8/6

6:05 am-12:15 pm

1 stop7h 10m

Colorado Springs

Tue 8/11

1:21 pm-10:36 pm

1 stop8h 15m

$322

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

Thu 8/6

6:05 am-12:15 pm

1 stop7h 10m

Colorado Springs

Tue 8/11

11:27 am-10:36 pm

2 stops10h 09m

$327

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

Sat 6/13

5:25 am-8:45 am

1 stop4h 20m

Colorado Springs

Tue 6/16

6:10 pm-12:05 am

1 stop4h 55m

$339

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

Thu 7/9

1:18 pm-10:41 pm

2 stops10h 23m

Colorado Springs

Sat 7/11

11:10 am-5:52 pm

1 stop5h 42m

$342

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

Sat 8/1

5:25 am-8:45 am

1 stop4h 20m

Colorado Springs

Thu 8/13

1:15 pm-4:35 pm

Nonstop2h 20m

$344

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

Sat 8/1

1:00 pm-8:35 pm

2 stops8h 35m

Colorado Springs

Thu 8/13

1:15 pm-4:35 pm

Nonstop2h 20m

$349
Quickest round-trip

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

Wed 8/19

3:35 pm-5:00 pm

Nonstop2h 25m

Colorado Springs

Sat 8/22

10:40 am-2:00 pm

Nonstop2h 20m

$351

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

Sat 8/1

1:00 pm-8:35 pm

2 stops8h 35m

Colorado Springs

Thu 8/13

1:30 pm-8:20 pm

1 stop5h 50m

$359

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

Mon 7/6

5:15 am-8:55 am

1 stop4h 40m

Colorado Springs

Fri 7/10

2:40 pm-6:00 pm

Nonstop2h 20m

$361

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

Sat 6/13

5:40 pm-7:15 pm

Nonstop2h 35m

Colorado Springs

Tue 6/16

6:10 pm-12:05 am

1 stop4h 55m

$363

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 $319. 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 $410.

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 $281 when looking at flights departing in the afternoon. Flights to Colorado Springs are more costly in the evening, with an average ticket price of $381. 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 50% 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

$371

Fastest flight time

2h 30m

Direct flights

Every day

Airports in Colorado Springs

1 airport
The best flight deal from Chicago Midway Airport to Colorado Springs found on momondo in the last 72 hours is $371
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
7.9
4,271 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.

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