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Cheap flights from Chicago Midway Airport to Denver from $73

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 Denver departing on 10/28. 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 Denver

Cheap round-trip flights

Southwest Logo
5:00 am - 11:15 amMDW-COS
7h 15m1 stop
Southwest Logo
5:15 am - 11:15 amCOS-MDW
5h 00m1 stop
$161Southwest
Find Deal
Tue, Nov 11 - Wed, Nov 19
Southwest Logo
1:55 pm - 8:25 pmMDW-COS
7h 30m2 stops
Southwest Logo
5:15 am - 11:15 amCOS-MDW
5h 00m1 stop
$166Southwest
Find Deal
Tue, Nov 11 - Wed, Nov 19
Southwest Logo
1:55 pm - 8:25 pmMDW-COS
7h 30m2 stops
Southwest Logo
5:15 am - 2:55 pmCOS-MDW
8h 40m2 stops
$176Southwest
Find Deal
Tue, Nov 11 - Wed, Nov 19
Southwest Logo
6:25 am - 11:55 amMDW-COS
6h 30m1 stop
Southwest Logo
5:30 pm - 10:40 pmCOS-MDW
4h 10m1 stop
$177Southwest
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Wed, Oct 22 - Wed, Oct 29
Southwest Logo
3:25 pm - 11:00 pmMDW-COS
8h 35m2 stops
Southwest Logo
7:10 am - 2:25 pmCOS-MDW
6h 15m1 stop
$182Southwest
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Wed, Oct 22 - Wed, Oct 29
Delta Logo
6:00 am - 12:06 pmMDW-COS
7h 06m1 stop
Delta Logo
6:00 am - 3:26 pmCOS-MDW
8h 26m1 stop
$217Delta
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Wed, Oct 1 - Sat, Oct 4
Southwest Logo
2:45 pm - 4:10 pmMDW-COS
2h 25mnonstop
Southwest Logo
6:50 am - 4:30 pmCOS-MDW
8h 40m1 stop
$218Southwest
Find Deal
Wed, Oct 1 - Sat, Oct 4
Delta Logo
9:59 am - 5:19 pmMDW-COS
8h 20m2 stops
Delta Logo
1:42 pm - 11:32 pmCOS-MDW
8h 50m1 stop
$222Delta
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Sat, Dec 6 - Wed, Dec 10
Logo
6:20 am - 8:51 amMDW-COS
27h 31m2 stops
Logo
10:11 am - 12:30 amCOS-MDW
13h 19m1 stop
$266
Find Deal
Thu, Oct 30 - Mon, Nov 3
Delta Logo
9:59 am - 5:19 pmMDW-COS
8h 20m2 stops
Delta Logo
8:00 am - 11:32 pmCOS-MDW
14h 32m2 stops
$278Delta
Find Deal
Sat, Dec 6 - Wed, Dec 10

Southwest flights from Chicago Midway Airport to Colorado Springs

Our best Southwest deals on Chicago Midway Airport to Colorado Springs flight tickets
Southwest
Nov 11
MDW5:00 amChicago Midway
7h 15m
1 stop
COS11:15 amColorado Springs
Nov 19
COS5:15 amColorado Springs
5h 00m
1 stop
MDW11:15 amChicago Midway
$161
Find similar
Southwest
Nov 11
MDW1:55 pmChicago Midway
7h 30m
2 stops
COS8:25 pmColorado Springs
Nov 19
COS5:15 amColorado Springs
5h 00m
1 stop
MDW11:15 amChicago Midway
$166
Find similar
Southwest
Nov 11
MDW1:55 pmChicago Midway
7h 30m
2 stops
COS8:25 pmColorado Springs
Nov 19
COS5:15 amColorado Springs
8h 40m
2 stops
MDW2:55 pmChicago Midway
$176
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
Oct 1
MDW6:00 amChicago Midway
7h 06m
1 stop
COS12:06 pmColorado Springs
Oct 4
COS6:00 amColorado Springs
8h 26m
1 stop
MDW3:26 pmChicago Midway
$217
Find similar
Delta
Dec 6
MDW9:59 amChicago Midway
8h 20m
2 stops
COS5:19 pmColorado Springs
Dec 10
COS1:42 pmColorado Springs
8h 50m
1 stop
MDW11:32 pmChicago Midway
$222
Find similar
Delta
Dec 6
MDW9:59 amChicago Midway
8h 20m
2 stops
COS5:19 pmColorado Springs
Dec 10
COS8:00 amColorado Springs
14h 32m
2 stops
MDW11:32 pmChicago Midway
$278
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 September 14, 2025.
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 11/11

5:00 am-11:15 am

1 stop7h 15m

Colorado Springs

Wed 11/19

5:15 am-11:15 am

1 stop5h 00m

$161

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

Tue 11/11

1:55 pm-8:25 pm

2 stops7h 30m

Colorado Springs

Wed 11/19

5:15 am-11:15 am

1 stop5h 00m

$166

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

Tue 11/11

1:55 pm-8:25 pm

2 stops7h 30m

Colorado Springs

Wed 11/19

5:15 am-2:55 pm

2 stops8h 40m

$176

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

Wed 10/22

6:25 am-11:55 am

1 stop6h 30m

Colorado Springs

Wed 10/29

5:30 pm-10:40 pm

1 stop4h 10m

$177

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

Wed 10/22

3:25 pm-11:00 pm

2 stops8h 35m

Colorado Springs

Wed 10/29

7:10 am-2:25 pm

1 stop6h 15m

$182

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

Wed 10/1

6:00 am-12:06 pm

1 stop7h 06m

Colorado Springs

Sat 10/4

6:00 am-3:26 pm

1 stop8h 26m

$217

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

Wed 10/1

2:45 pm-4:10 pm

Nonstop2h 25m

Colorado Springs

Sat 10/4

6:50 am-4:30 pm

1 stop8h 40m

$218

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

Sat 12/6

9:59 am-5:19 pm

2 stops8h 20m

Colorado Springs

Wed 12/10

1:42 pm-11:32 pm

1 stop8h 50m

$222

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

Thu 10/30

6:20 am-8:51 am

2 stops27h 31m

Colorado Springs

Mon 11/3

10:11 am-12:30 am

1 stop13h 19m

$266

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

Sat 12/6

9:59 am-5:19 pm

2 stops8h 20m

Colorado Springs

Wed 12/10

8:00 am-11:32 pm

2 stops14h 32m

$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 Denver 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 $344. 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 $394.

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 $283 when looking at flights departing at noon. Flights to Colorado Springs are more costly in the evening, with an average ticket price of $435. 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?

No. A direct flight is the cheapest option for a flight between Chicago Midway Airport to Colorado Springs.

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

$135

Fastest flight time

2h 25m

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 $135. The best round-trip flight deal from Chicago Midway Airport to Colorado Springs found on momondo in the last 72 hours is $239.
The fastest flight from Chicago Midway Airport to Colorado Springs takes 2h 25m
Direct flights go from Chicago Midway Airport to Colorado Springs every day.
There is 1 airport near Colorado Springs: 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 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 $248Free CancellationRating
8.0
4,245 reviews
Search Southwest flights

  • Southwest Flights From Chicago Midway Airport to Colorado Springs

    Southwest flies from Chicago Midway Airport to Colorado Springs around 5 times per week, with 4,245 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 $248 (round-trip), much lower than the average airfare cost of $332 for Southwest flights on this route.

Traveling to a place near Denver?

Book flights to Denver 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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