HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$79+ 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 10/22. Fares are subject to change and may not be available on all flights or dates of travel.
COS — MDW
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Colorado Springs to Midway with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap 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 September 16, 2025.

Round-trip from

$167
(Southwest)

One-way from

$79
(Southwest)

Popular in

April

Cheapest in

August

Average price

$320

Good round-trip deal

$304 or less

Good one-way deal

$228 or less
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 ($51 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 September 2025
Search Deals
Price to beat on a round-trip flight from Colorado Springs to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Colorado Springs to Chicago Midway.
Search Deals

Find 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 September 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.
Wed 10/295:30 pmCOS - MDW
1 stop4h 10mSouthwest
Sat 11/16:00 pmMDW - COS
Nonstop2h 35mSouthwest
Deal found 9/14$167
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.
Tue 10/286:15 amCOS - MDW
1 stop6h 20mSouthwest
Tue 11/45:00 amMDW - COS
1 stop7h 15mSouthwest
Deal found 9/16$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.
Fri 12/56:35 amCOS - MDW
1 stop7h 25mSouthwest
Mon 12/85:00 amMDW - COS
1 stop7h 15mSouthwest
Deal found 9/15$199
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.
Wed 10/81:55 pmCOS - MDW
Nonstop2h 20mSouthwest
Fri 10/1012:00 pmMDW - COS
Nonstop2h 35mSouthwest
Deal found 9/15$254
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.
Wed 10/81:55 pmCOS - MDW
Nonstop2h 20mSouthwest
Sun 10/125:50 pmMDW - COS
1 stop7h 20mSouthwest
Deal found 9/15$264
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.
Wed 10/155:30 pmCOS - MDW
1 stop4h 10mSouthwest
Wed 10/225:45 amMDW - COS
2 stops8h 20mSouthwest
Deal found 9/15$269

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 September 16, 2025.
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

Wed 10/29

5:30 pm-10:40 pm

1 stop4h 10m

Chicago Midway

Sat 11/1

6:00 pm-7:35 pm

Nonstop2h 35m

$167

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Tue 10/28

12:30 pm-9:55 pm

1 stop8h 25m

Chicago Midway

Tue 11/4

11:25 am-7:25 pm

2 stops9h 00m

$182

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Fri 12/5

6:35 am-3:00 pm

1 stop7h 25m

Chicago Midway

Mon 12/8

5:00 am-11:15 am

1 stop7h 15m

$199

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Thu 10/16

5:20 pm-12:05 am

1 stop5h 45m

Chicago Midway

Thu 10/23

6:25 pm-11:20 pm

1 stop5h 55m

$264

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Wed 10/15

5:30 pm-10:40 pm

1 stop4h 10m

Chicago Midway

Wed 10/22

5:30 am-10:50 am

1 stop6h 20m

$264

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Wed 10/8

5:30 pm-10:40 pm

1 stop4h 10m

Chicago Midway

Sun 10/12

6:45 am-1:00 pm

1 stop7h 15m

$274

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Thu 10/23

2:10 pm-5:30 pm

Nonstop2h 20m

$79

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Wed 10/22

1:55 pm-5:15 pm

Nonstop2h 20m

$79

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Sat 11/15

5:00 am-1:55 pm

1 stop7h 55m

$89

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Wed 12/31

2:25 pm-10:10 pm

1 stop6h 45m

$89

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 15 results
1
2

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, April is the cheapest month in which you can book a flight from Colorado Springs to Chicago Midway Airport (average of $160). Flying from Colorado Springs to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 COS to MDW?

Find hourly flight availability from Colorado Springs to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 16, 2025.

It’s optimal to fly from Colorado Springs to Chicago Midway Airport at noon. By choosing this option you can save up to 15% on the cost of your flight, compared to a flight in the afternoon.

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 September 16, 2025.
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
4,242 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 4h 10m. Fly via Southwest to get the fastest option. The distance between Colorado Springs and Chicago Midway Airport is about 915 mi.

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

    Southwest, at $233, was found to be the cheapest airline from Colorado Springs to Chicago Midway Airport.. Users have found that Southwest is 38% cheaper than the other options available to this destination.

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

    On average you can expect to pay $307 for a flight from Colorado Springs to Chicago Midway Airport. The cheapest flight overall is $179 while the most popular route, (Colorado Springs - Chicago Midway) is currently priced at $167.

  • 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, April is the cheapest month in which you can book a flight from Colorado Springs to Chicago Midway Airport (average of $160). Flying from Colorado Springs to Chicago Midway Airport in November is currently the most expensive (average of $249). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$233Average$315FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.