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Midway

$100+ Cheap flights from Colorado Springs (COS) to Midway (MDW)

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 2/25. Fares are subject to change and may not be available on all flights or dates of travel.
COS — MDW
Feb 27 — Mar 61
Fri 2/27
Fri 3/6
1 adult, Economy
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Cheap flight deals from Colorado Springs to Midway

Cheapest flights from Colorado Springs to Midway
Explore the most affordable flight options available from Colorado Springs to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 28, 2026.

This Delta deal was found by Cheapflights users on 1/27. 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.
Tue 3/101:28 pm
COS
-
MDW
1 stop8h 03m
Delta
Tue 3/246:00 am
MDW
-
COS
1 stop7h 33m
Delta
Deal found 1/27$224
This Delta deal was found by Cheapflights users on 1/27. 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.
Mon 3/91:28 pm
COS
-
MDW
1 stop8h 03m
Delta
Tue 3/246:00 am
MDW
-
COS
1 stop7h 33m
Delta
Deal found 1/27$232
This Delta deal was found by Cheapflights users on 1/26. 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 7/31:40 pm
COS
-
MDW
1 stop7h 05m
Delta
Tue 7/76:00 am
MDW
-
COS
1 stop7h 48m
Delta
Deal found 1/26$249
This Delta deal was found by Cheapflights users on 1/28. 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.
Tue 8/2510:57 am
COS
-
MDW
1 stop6h 08m
Delta
Sat 8/291:00 pm
MDW
-
COS
2 stops10h 29m
Delta
Deal found 1/28$254
This Southwest deal was found by Cheapflights users on 1/28. 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 2/2410:15 am
COS
-
MDW
1 stop11h 25m
Southwest
Sat 2/281:55 pm
MDW
-
COS
2 stops8h 35m
Southwest
Deal found 1/28$260
This Delta deal was found by Cheapflights users on 1/25. 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.
Thu 3/126:20 am
COS
-
MDW
2 stops10h 34m
Delta
Tue 3/176:00 am
MDW
-
COS
1 stop7h 33m
Delta
Deal found 1/25$262
This Southwest deal was found by Cheapflights users on 1/27. 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 2/174:20 pm
COS
-
MDW
1 stop5h 05m
Southwest
Thu 2/193:40 pm
MDW
-
COS
1 stop7h 15m
Southwest
Deal found 1/27$266
This Southwest deal was found by Cheapflights users on 1/27. 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 2/174:20 pm
COS
-
MDW
1 stop5h 05m
Southwest
Fri 2/2010:50 am
MDW
-
COS
1 stop9h 30m
Southwest
Deal found 1/27$274

Find flight deals from Colorado Springs to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Colorado Springs (COS) to Midway (MDW). 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 January 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$224
(Delta)

One-way from

$100
(Delta)

Popular in

April

Cheapest in

August

Average price

$284
Provider with most accurate pricing for Colorado Springs-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Colorado Springs-Chicago Midway flights.
Search Deals
From Colorado Springs to Chicago Midway
Search Deals
One-way flight from Colorado Springs to Chicago Midway
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($48 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($26 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Colorado Springs to Midway 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 January 28, 2026.
Use the filters below to find and compare flights from Colorado Springs to Chicago Midway Airport that are best for you.

Fly from

Colorado Springs

Fly to

Midway

Route

Depart

Return

Price

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Fri 7/3

1:40 pm-9:45 pm

1 stop7h 05m

Chicago Midway

Tue 7/7

6:00 am-12:48 pm

1 stop7h 48m

$249

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Mon 2/23

5:40 pm-5:05 am

1 stop10h 25m

Chicago Midway

Sun 3/1

5:15 am-9:30 am

1 stop5h 15m

$254

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Tue 2/24

10:15 am-10:40 pm

1 stop11h 25m

Chicago Midway

Sat 2/28

3:15 pm-6:25 pm

1 stop4h 10m

$254

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Thu 3/12

6:20 am-5:54 pm

2 stops10h 34m

Chicago Midway

Tue 3/17

6:00 am-12:33 pm

1 stop7h 33m

$262

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Thu 3/12

8:55 pm-5:00 am

1 stop7h 05m

Chicago Midway

Tue 3/17

5:50 pm-11:35 pm

1 stop6h 45m

$266

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Thu 4/9

7:20 pm-5:00 am

1 stop8h 40m

Chicago Midway

Tue 4/14

2:10 pm-9:20 pm

2 stops8h 10m

$271

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Thu 4/23

1:13 pm-10:28 pm

1 stop8h 15m

Chicago Midway

Mon 4/27

6:00 am-12:17 pm

1 stop7h 17m

$283

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Fri 2/20

5:35 am-3:05 pm

1 stop8h 30m

Chicago Midway

Mon 2/23

3:25 pm-10:45 pm

1 stop8h 20m

$291

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Thu 2/19

5:35 am-2:20 pm

2 stops7h 45m

Chicago Midway

Sat 2/21

1:55 pm-9:30 pm

2 stops8h 35m

$293

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Wed 2/25

1:22 pm-10:31 pm

1 stop8h 09m

$100

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

Showing 1-10 of 15 results
1
2

Compare providers for flights from Colorado Springs to Midway

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 Colorado Springs to Midway in January.
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 Colorado Springs-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Colorado Springs-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Colorado Springs-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Colorado Springs-Chicago Midway Airport 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 Colorado Springs-Chicago Midway Airport 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 Colorado Springs to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Colorado Springs 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 Colorado Springs to Chicago Midway Airport

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

Currently, February is the cheapest month in which you can book a flight from Colorado Springs to Chicago Midway Airport (average of $60). Flying from Colorado Springs to Chicago Midway Airport in July is currently the most expensive (average of $156). 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 Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated January 28, 2026.
Peruse reviews from past customers who have flown with Southwest from Colorado Springs to Chicago Midway Airport 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
4,267 reviews

Boarding

8.1

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

8.0

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
4,267 reviews
Southwest
8.0
Very good
4,267 reviews

Boarding

8.1

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

8.0

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 Colorado Springs to Midway. 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 from for flights from Colorado Springs to Chicago Midway?

    Colorado Springs (COS), located 6.7 mi from the city center, is the airport you fly out of when you book flights from Colorado Springs to Chicago Midway. 1 airline have flights from Colorado Springs to Chicago Midway on a regular basis. Booking flights from Colorado Springs to Chicago Midway should not be difficult; the airport handles an average of 0 outbound flights to Chicago Midway per day.

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

    There are many flights that can get you from Colorado Springs to Chicago Midway Airport in 7h 05m. Fly via Delta or Southwest to get the fastest option. The distance between Colorado Springs and Chicago Midway Airport is about 915 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    Southwest, at $224, was found to be the cheapest airline from Colorado Springs to Chicago Midway Airport.. Users have found that Southwest is 41% cheaper than the other options available to this destination.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Colorado Springs to Midway 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 Colorado Springs to Chicago Midway Airport?

    Currently, February is the cheapest month in which you can book a flight from Colorado Springs to Chicago Midway Airport (average of $60). Flying from Colorado Springs to Chicago Midway Airport in July is currently the most expensive (average of $156). 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

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Top airline flying from Colorado Springs to Midway

Discover the top airline that operate flights from Colorado Springs to Midway. 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 January 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$224Average$321FlexibilityNo cancel feeOn-time63%

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