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$111+ Cheap flights from Midway (MDW) to Colorado Springs (COS)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/15. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — COS
Apr 22 — Apr 291
Wed 4/22
Wed 4/29
1 adult, Economy
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Cheap flight deals from Midway to Colorado Springs

Cheapest flights from Midway to Colorado Springs
Explore the most affordable flight options available from Midway to Colorado Springs. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 23, 2026.

This Southwest deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/124:00 pm
MDW
-
COS
1 stop5h 15m
Southwest
Tue 5/192:30 pm
COS
-
MDW
1 stop6h 15m
Southwest
Deal found 3/20$221
This Southwest deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/127:25 am
MDW
-
COS
2 stops7h 25m
Southwest
Tue 5/126:50 pm
COS
-
MDW
1 stop9h 35m
Southwest
Deal found 3/20$226
This Southwest deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/156:10 am
MDW
-
COS
1 stop6h 55m
Southwest
Thu 4/164:05 pm
COS
-
MDW
1 stop6h 50m
Southwest
Deal found 3/19$231
This Southwest deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/305:30 am
MDW
-
COS
1 stop5h 30m
Southwest
Mon 5/44:05 pm
COS
-
MDW
1 stop6h 50m
Southwest
Deal found 3/19$241
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/54:00 pm
MDW
-
COS
1 stop5h 15m
Southwest
Tue 5/126:30 am
COS
-
MDW
1 stop7h 55m
Southwest
Deal found 3/23$243
This Southwest deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/45:15 pm
MDW
-
COS
1 stop6h 00m
Southwest
Mon 5/115:00 am
COS
-
MDW
2 stops8h 55m
Southwest
Deal found 3/19$246
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/2510:00 am
MDW
-
COS
1 stop7h 15m
Southwest
Tue 4/286:50 pm
COS
-
MDW
1 stop9h 35m
Southwest
Deal found 3/23$267

Find flight deals from Midway to Colorado Springs

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Colorado Springs (COS). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated March 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$221
(Southwest)

One-way from

$111
(Delta)

Popular in

September

Cheapest in

June

Average price

$537

Good one-way deal

$165 or less
Provider with most accurate pricing for Chicago Midway-Colorado Springs flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Colorado Springs flights.
Search Deals
From Chicago Midway to Colorado Springs
Search Deals
One-way flight from Chicago Midway to Colorado Springs
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($26 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals
Price to beat on a one-way flight from Chicago Midway to Colorado Springs.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway 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, Cheapflights users made 2,558,603 searches. Data last updated March 23, 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

Mon 5/4

5:30 am-10:00 am

1 stop5h 30m

Colorado Springs

Mon 5/11

7:20 pm-5:00 am

1 stop8h 40m

$241

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

Sat 4/25

10:15 am-5:35 pm

1 stop8h 20m

Colorado Springs

Sun 4/26

5:05 pm-12:50 am

2 stops6h 45m

$336

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

Mon 6/1

3:40 pm-11:50 pm

1 stop9h 10m

Colorado Springs

Thu 6/4

9:05 pm-5:10 am

1 stop7h 05m

$371

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

Mon 6/1

4:35 pm-12:05 am

2 stops8h 30m

Colorado Springs

Fri 6/5

9:05 pm-5:10 am

1 stop7h 05m

$376

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

Fri 5/8

6:25 pm-11:50 pm

1 stop6h 25m

Colorado Springs

Sun 5/10

5:55 am-2:25 pm

2 stops7h 30m

$376

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

Sun 5/31

5:10 am-10:40 am

1 stop6h 30m

Colorado Springs

Thu 6/4

12:20 pm-12:35 am

2 stops11h 15m

$376

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

Fri 5/1

5:30 am-1:35 pm

2 stops9h 05m

Colorado Springs

Sun 5/3

5:05 pm-12:50 am

2 stops6h 45m

$381
Quickest round-trip

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

Mon 5/25

6:00 am-9:20 am

1 stop4h 20m

Colorado Springs

Sun 5/31

8:35 pm-5:25 am

1 stop7h 50m

$412

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

Tue 5/26

2:10 pm-9:20 pm

2 stops8h 10m

Colorado Springs

Sun 5/31

5:55 am-2:25 pm

2 stops7h 30m

$422
Cheapest one-way

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

Thu 6/11

6:40 pm-1:20 am

1 stop7h 40m

$186

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/22

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

Compare providers for flights from Midway to Colorado Springs

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Colorado Springs in March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-Colorado Springs flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Colorado Springs flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Colorado Springs flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Colorado Springs flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Colorado Springs flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Midway to Colorado Springs

Have a flexible travel schedule? Discover the best time to fly to Colorado Springs from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Colorado Springs

What is the cheapest month to book a flight from Chicago Midway Airport to Colorado Springs?

Currently, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Colorado Springs (average of $83). Flying from Chicago Midway Airport to Colorado Springs in February is currently the most expensive (average of $187). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Reviews of airlines servicing Colorado Springs

Get insights into the airlines that provide service to Colorado Springs. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Colorado Springs. Reviews last updated March 23, 2026.
Peruse reviews from past customers who have flown with Southwest from Chicago Midway Airport to Colorado Springs to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,331 reviews

Overall

8.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,331 reviews
Southwest
8.0
Very good
4,331 reviews

Overall

8.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

Find useful and relevant information for your journey from Midway to Colorado Springs. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Colorado Springs from Chicago Midway?

    For a flight from Chicago Midway to Colorado Springs, you will be flying into Colorado Springs. Colorado Springs (COS) is just 6.7 mi from the center of the city. Colorado Springs is the only Colorado Springs airport and it handles 0 inbound flights from Chicago Midway per day. 1 airline has flights to Colorado Springs from Chicago Midway on a regular basis.

  • How long is the flight from Chicago Midway Airport to Colorado Springs?

    For as low as $241, Southwest can have you in Colorado Springs from Chicago Midway Airport in 5h 30m. The distance from Chicago Midway Airport to Colorado Springs is about 915 mi.

  • What is the cheapest airline to fly from Chicago Midway Airport to Colorado Springs round-trip?

    Our cheapest airline available from Chicago Midway Airport to Colorado Springs is Southwest. Our recent data shows that you can find tickets from as low as $241 on this airline. This flight start at 41% lower than the current average price 3 months from now.

  • What are the cheapest flights from Chicago Midway Airport to Colorado Springs?

    While on average a flight from Chicago Midway Airport to Colorado Springs is generally $165, our data shows the cheapest flight currently is $149. When looking at the most popular route, (Chicago Midway - Colorado Springs), you can expect to pay $221 for that flight.

  • Can I find deals for flights from Midway to Colorado Springs that include hotel bookings?

    Yes. In addition to deals on Midway to Colorado Springs flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Colorado Springs?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Colorado Springs.

  • Can I find deals for business class flights from Midway to Colorado Springs?

    Yes. Cheapflights offers flight deals from Midway to Colorado Springs by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Colorado Springs?

    Currently, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Colorado Springs (average of $83). Flying from Chicago Midway Airport to Colorado Springs in February is currently the most expensive (average of $187). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Colorado Springs?

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

Browse thousands of different options on Cheapflights for your next trip

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Top airline flying from Midway to Colorado Springs

Discover the top airline that operate flights from Midway to Colorado Springs. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$255Average$398FlexibilityNo cancel feeOn-time63%

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