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$79+ 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 10/28. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — COS
oct. 16 — oct. 231
jue. 10/16
jue. 10/23
1 adult, Economy
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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 septiembre 16, 2025.

Round-trip from

$177
(Southwest)

One-way from

$79
(Southwest)

Popular in

September

Cheapest in

June

Average price

$457

Good round-trip deal

$239 or less

Good one-way deal

$135 or less
From Chicago Midway to Colorado Springs
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One-way flight from Chicago Midway to Colorado Springs
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Highest demand for flights based on searches. 14% potential increase in price ($60 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Chicago Midway to Colorado Springs.
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Price to beat on a one-way flight from Chicago Midway to Colorado Springs.
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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 septiembre 16, 2025.

This Southwest deal was found by Cheapflights users on 9/14. 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.
mié. 10/226:25 amMDW - COS
1 stop6h 30mSouthwest
mié. 10/295:30 pmCOS - MDW
1 stop4h 10mSouthwest
Deal found 9/14$177
This Southwest deal was found by Cheapflights users on 9/15. 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.
vie. 10/312:30 pmMDW - COS
1 stop6h 45mSouthwest
lun. 11/312:15 pmCOS - MDW
1 stop7h 40mSouthwest
Deal found 9/15$199
This Southwest deal was found by Cheapflights users on 9/16. 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.
mar. 10/145:45 amMDW - COS
2 stops8h 20mSouthwest
vie. 10/176:15 pmCOS - MDW
1 stop4h 15mSouthwest
Deal found 9/16$204
This Delta deal was found by Cheapflights users on 9/16. 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.
sáb. 12/69:59 amMDW - COS
2 stops8h 20mDelta
mié. 12/101:42 pmCOS - MDW
1 stop8h 50mDelta
Deal found 9/16$222
This Southwest deal was found by Cheapflights users on 9/14. 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.
sáb. 11/155:15 amMDW - COS
1 stop8h 35mSouthwest
mar. 11/2512:05 pmCOS - MDW
1 stop11h 50mSouthwest
Deal found 9/14$234
This Southwest deal was found by Cheapflights users on 9/16. 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.
sáb. 10/46:00 pmMDW - COS
Nonstop2h 35mSouthwest
mar. 10/74:25 pmCOS - MDW
1 stop6h 40mSouthwest
Deal found 9/16$249
This Southwest deal was found by Cheapflights users on 9/14. 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.
vie. 11/217:50 amMDW - COS
Nonstop2h 40mSouthwest
lun. 11/246:35 pmCOS - MDW
1 stop4h 30mSouthwest
Deal found 9/14$254

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 septiembre 16, 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

mié. 10/22

6:25 am-11:55 am

1 stop6h 30m

Colorado Springs

mié. 10/29

5:30 pm-10:40 pm

1 stop4h 10m

$177

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

vie. 10/31

2:30 pm-8:15 pm

1 stop6h 45m

Colorado Springs

lun. 11/3

12:15 pm-8:55 pm

1 stop7h 40m

$199

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

sáb. 12/6

9:59 am-5:19 pm

2 stops8h 20m

Colorado Springs

mié. 12/10

1:42 pm-11:32 pm

1 stop8h 50m

$222

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

mar. 10/14

5:30 am-10:50 am

1 stop6h 20m

Colorado Springs

vie. 10/17

5:20 pm-12:05 am

1 stop5h 45m

$251

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

vie. 11/21

7:50 am-9:30 am

Nonstop2h 40m

Colorado Springs

lun. 11/24

6:35 pm-12:05 am

1 stop4h 30m

$254

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

sáb. 10/4

8:30 am-1:50 pm

1 stop6h 20m

Colorado Springs

mar. 10/7

4:25 pm-12:05 am

1 stop6h 40m

$259

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

mar. 10/28

4:00 pm-5:35 pm

Nonstop2h 35m

$79

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

mié. 10/22

5:30 am-10:50 am

1 stop6h 20m

$89

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

mar. 10/21

6:25 am-11:55 am

1 stop6h 30m

$89

ChicagoColorado Springs

MDW - COS

MDWCOS

Chicago Midway

sáb. 11/1

5:00 am-12:15 pm

1 stop8h 15m

$89

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 17 results
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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 $316). Flying from Chicago Midway Airport to Colorado Springs in March is currently the most expensive (average of $412). 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 septiembre 16, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago Midway Airport to Colorado Springs at noon. If you’re flexible enough to do this you can expect to save up to 15% on your trip compared to booking a flight in the morning.

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 septiembre 16, 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
4,242 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

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 $177, Southwest can have you in Colorado Springs from Chicago Midway Airport in 6h 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 $248 on this airline. This flight start at 31% 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 $258, our data shows the cheapest flight currently is $125. When looking at the most popular route, (Chicago Midway - Colorado Springs), you can expect to pay $177 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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Colorado Springs (average of $316). Flying from Chicago Midway Airport to Colorado Springs in March is currently the most expensive (average of $412). 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

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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 septiembre 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$248Average$332FlexibilityNo cancel feeOn-time63%

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