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$109+ 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 8/27. Fares are subject to change and may not be available on all flights or dates of travel.
COS — MDW
Aug 2 — Aug 91
Sat 8/2
Sat 8/9
1 adult, Economy
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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 July 28, 2025.

Round-trip from

$217
(Southwest)

One-way from

$109
(Southwest)

Popular in

April

Cheapest in

August

Average price

$346

Good round-trip deal

$275 or less

Good one-way deal

$171 or less
From Colorado Springs to Chicago Midway
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One-way flight from Colorado Springs to Chicago Midway
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Highest demand for flights based on searches. 6% potential increase in price ($27 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($24 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Price to beat on a round-trip flight from Colorado Springs to Chicago Midway.
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Price to beat on a one-way flight from Colorado Springs to Chicago Midway.
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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 July 28, 2025.

This Southwest deal was found by Cheapflights users on 7/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/258:20 amCOS - MDW
Nonstop2h 25mSouthwest
Sat 11/16:00 pmMDW - COS
Nonstop2h 35mSouthwest
Deal found 7/26$217
This Delta deal was found by Cheapflights users on 7/26. 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.
Sat 10/256:00 amCOS - MDW
1 stop8h 30mDelta
Sat 11/16:00 amMDW - COS
2 stops14h 38mDelta
Deal found 7/26$242

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 July 28, 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

Sat 10/25

8:20 am-11:45 am

Nonstop2h 25m

Chicago Midway

Sat 11/1

6:00 pm-7:35 pm

Nonstop2h 35m

$217

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Sat 10/25

6:00 am-3:30 pm

1 stop8h 30m

Chicago Midway

Sat 11/1

6:00 am-7:38 pm

2 stops14h 38m

$242

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Wed 8/27

11:55 am-3:15 pm

Nonstop2h 20m

$109

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Tue 11/18

1:40 pm-9:44 pm

1 stop7h 04m

$119

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

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 July 28, 2025.

It’s optimal to fly from Colorado Springs to Chicago Midway Airport at noon. By choosing this option you can save up to 14% 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 July 28, 2025.
Peruse reviews from past customers who have flown with Southwest and Delta 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
4,237 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

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
4,237 reviews
Southwest
8.0
Very good
4,237 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

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.
Delta
8.0
Very good
7,971 reviews
Southwest
8.0
Very good
4,237 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

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 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 1 outbound flight to Chicago Midway per day.

  • What are the cheapest airlines flying from Colorado Springs to Chicago Midway Airport round-trip?

    Southwest, at $217, was found to be the cheapest airline from Colorado Springs to Chicago Midway Airport. An alternate airline flying to your destination would be Delta. Users have found that Southwest is 46% 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 $278 for a flight from Colorado Springs to Chicago Midway Airport. The cheapest flight overall is $134 while the most popular route, (Colorado Springs - Chicago Midway) is currently priced at $217.

  • 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
Valparaiso
Chesterton

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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 July 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$281Average$325FlexibilityNo cancel feeOn-time63%

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