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$80+ 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 1/17. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — COS
Nov 21 — Nov 281
Fri 11/21
Fri 11/28
1 adult, Economy
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Find 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 October 22, 2025.

This Southwest deal was found by Cheapflights users on 10/20. 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 12/95:00 amMDW - COS
1 stop7h 15mSouthwest
Tue 12/165:15 amCOS - MDW
1 stop5h 05mSouthwest
Deal found 10/20$178
This Delta deal was found by Cheapflights users on 10/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/51:14 pmMDW - COS
2 stops10h 11mDelta
Mon 12/86:00 pmCOS - MDW
2 stops14h 41mDelta
Deal found 10/21$211
This Southwest deal was found by Cheapflights users on 10/20. 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.
Thu 12/111:55 pmMDW - COS
2 stops7h 30mSouthwest
Thu 12/183:10 pmCOS - MDW
Nonstop2h 20mSouthwest
Deal found 10/20$246
This Southwest deal was found by Cheapflights users on 10/21. 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 12/45:25 amMDW - COS
1 stop9h 25mSouthwest
Sun 12/73:10 pmCOS - MDW
Nonstop2h 20mSouthwest
Deal found 10/21$257
This Southwest deal was found by Cheapflights users on 10/21. 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.
Fri 12/53:15 pmMDW - COS
1 stop6h 10mSouthwest
Mon 12/85:15 amCOS - MDW
1 stop5h 05mSouthwest
Deal found 10/21$262
This Southwest deal was found by Cheapflights users on 10/20. 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 11/115:25 amMDW - COS
1 stop9h 25mSouthwest
Tue 11/185:15 amCOS - MDW
1 stop5h 05mSouthwest
Deal found 10/20$266
This Delta deal was found by Cheapflights users on 10/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/66:00 amMDW - COS
1 stop7h 36mDelta
Wed 12/108:10 amCOS - MDW
2 stops14h 37mDelta
Deal found 10/21$279

Cheap 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 October 22, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$171
(Southwest)

One-way from

$80
(Southwest)

Popular in

September

Cheapest in

June

Average price

$386
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. 19% potential increase in price ($96 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($21 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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 October 22, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Colorado Springs that are best for you.

Fly from

Midway

Fly to

Colorado Springs

Route

Depart

Return

Price

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

Fri 12/5

1:14 pm-10:25 pm

2 stops10h 11m

Colorado Springs

Mon 12/8

6:00 pm-9:41 am

2 stops14h 41m

$211

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

Thu 12/11

1:55 pm-8:25 pm

2 stops7h 30m

Colorado Springs

Thu 12/18

3:10 pm-6:30 pm

Nonstop2h 20m

$246

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

Thu 12/4

5:25 am-1:50 pm

1 stop9h 25m

Colorado Springs

Sun 12/7

3:10 pm-6:30 pm

Nonstop2h 20m

$257

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

Fri 12/5

3:15 pm-8:25 pm

1 stop6h 10m

Colorado Springs

Mon 12/8

5:15 am-11:20 am

1 stop5h 05m

$262

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

Tue 11/11

6:00 am-12:37 pm

1 stop7h 37m

Colorado Springs

Tue 11/18

8:00 am-6:18 pm

2 stops9h 18m

$276

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

Tue 11/11

5:25 am-1:50 pm

1 stop9h 25m

Colorado Springs

Tue 11/18

5:15 am-2:55 pm

2 stops8h 40m

$276

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

Sat 12/6

6:00 am-12:36 pm

1 stop7h 36m

Colorado Springs

Wed 12/10

8:10 am-11:47 pm

2 stops14h 37m

$279

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

Sat 1/17

5:10 am-10:45 am

1 stop6h 35m

$80

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

Tue 1/6

6:00 am-11:25 am

1 stop6h 25m

$92

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

Tue 1/13

6:00 am-11:25 am

1 stop6h 25m

$92

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/20

Showing 1-10 of 16 results
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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapTicketsDealPrice 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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Colorado Springs (average of $58). Flying from Chicago Midway Airport to Colorado Springs in September is currently the most expensive (average of $157). 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.

What is the cheapest time of day to fly from MDW to COS?

Find hourly flight availability from Midway to Colorado Springs. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 22, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago Midway Airport to Colorado Springs in the afternoon. If you’re flexible enough to do this you can expect to save up to 52% on your trip compared to booking a flight in the evening.

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 October 22, 2025.
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
4,235 reviews

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,235 reviews
Southwest
8.0
Very good
4,235 reviews

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 $246, Delta can have you in Colorado Springs from Chicago Midway Airport in 7h 30m. The distance from Chicago Midway Airport to Colorado Springs is about 915 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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 $248 on this airline. This flight start at 36% lower than the current average price 3 months from now.

  • 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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Colorado Springs (average of $58). Flying from Chicago Midway Airport to Colorado Springs in September is currently the most expensive (average of $157). 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?

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Cañon City

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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 October 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$248Average$343FlexibilityNo cancel feeOn-time63%

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