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$88+ 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 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
COS — MDW
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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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 October 30, 2025.

This Southwest deal was found by Cheapflights users on 10/28. 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.
Thu 12/115:15 amCOS - MDW
1 stop6h 25mSouthwest
Sat 12/135:15 amMDW - COS
1 stop8h 35mSouthwest
Deal found 10/28$278
This Southwest deal was found by Cheapflights users on 10/29. 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 12/610:35 amCOS - MDW
1 stop5h 10mSouthwest
Mon 12/83:15 pmMDW - COS
1 stop6h 10mSouthwest
Deal found 10/29$283
This Delta deal was found by Cheapflights users on 10/28. 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.
Sat 12/136:00 pmCOS - MDW
2 stops14h 54mDelta
Tue 12/166:00 amMDW - COS
1 stop7h 36mDelta
Deal found 10/28$286
This Delta deal was found by Cheapflights users on 10/29. 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 pmCOS - MDW
2 stops14h 54mDelta
Mon 12/86:00 amMDW - COS
1 stop7h 36mDelta
Deal found 10/29$288
This Delta deal was found by Cheapflights users on 10/28. 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.
Fri 12/58:10 amCOS - MDW
2 stops14h 37mDelta
Mon 12/86:00 amMDW - COS
1 stop7h 36mDelta
Deal found 10/28$323
This Southwest deal was found by Cheapflights users on 10/29. 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 12/135:00 amCOS - MDW
1 stop7h 55mSouthwest
Sat 1/38:00 amMDW - COS
Nonstop2h 40mSouthwest
Deal found 10/29$326
This Southwest deal was found by Cheapflights users on 10/30. 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 12/123:10 pmCOS - MDW
Nonstop2h 20mSouthwest
Sun 12/147:50 amMDW - COS
Nonstop2h 40mSouthwest
Deal found 10/30$331
This Southwest deal was found by Cheapflights users on 10/28. 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.
Fri 12/55:15 amCOS - MDW
1 stop5h 05mSouthwest
Sun 12/77:50 amMDW - COS
Nonstop2h 40mSouthwest
Deal found 10/28$337

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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$278
(Southwest)

One-way from

$88
(Kiwi.com)

Popular in

April

Cheapest in

January

Average price

$340

Good round-trip deal

$357 or less

Good one-way deal

$189 or less
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. 13% potential increase in price ($59 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($27 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 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

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 October 30, 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

Thu 12/11

5:15 am-12:40 pm

1 stop6h 25m

Chicago Midway

Sat 12/13

5:15 am-12:50 pm

1 stop8h 35m

$278

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Thu 12/11

8:10 am-11:47 pm

2 stops14h 37m

Chicago Midway

Sat 12/13

6:00 am-12:36 pm

1 stop7h 36m

$283

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Sat 12/13

6:00 pm-9:54 am

2 stops14h 54m

Chicago Midway

Tue 12/16

6:00 am-12:36 pm

1 stop7h 36m

$286

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Sat 12/6

6:00 pm-9:54 am

2 stops14h 54m

Chicago Midway

Mon 12/8

6:00 am-12:36 pm

1 stop7h 36m

$288

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Fri 1/16

1:21 pm-10:09 pm

1 stop7h 48m

Chicago Midway

Mon 1/19

6:00 am-12:23 pm

1 stop7h 23m

$318

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Fri 12/5

8:10 am-11:47 pm

2 stops14h 37m

Chicago Midway

Mon 12/8

6:00 am-12:36 pm

1 stop7h 36m

$323

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Sat 12/13

5:00 am-1:55 pm

1 stop7h 55m

Chicago Midway

Sat 1/3

8:00 am-9:40 am

Nonstop2h 40m

$326

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Fri 12/12

3:10 pm-6:30 pm

Nonstop2h 20m

Chicago Midway

Sun 12/14

7:50 am-9:30 am

Nonstop2h 40m

$331

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Thu 11/27

1:25 pm-6:25 pm

1 stop4h 00m

$131

Colorado SpringsChicago

COS - MDW

COSMDW

Colorado Springs

Thu 11/27

8:00 am-11:40 pm

2 stops14h 40m

$136

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 19 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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Colorado Springs-Chicago Midway Airport flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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, January is the cheapest month in which you can book a flight from Colorado Springs to Chicago Midway Airport (average of $58). Flying from Colorado Springs to Chicago Midway Airport in July is currently the most expensive (average of $155). 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 October 30, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Colorado Springs to Chicago Midway Airport as you normally would.

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 October 30, 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
4,243 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Overall

8.0

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
4,243 reviews
Southwest
8.0
Very good
4,243 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Overall

8.0

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 6h 25m. Fly via Southwest or Delta 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 $233, was found to be the cheapest airline from Colorado Springs to Chicago Midway Airport.. Users have found that Southwest is 37% 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 $335 for a flight from Colorado Springs to Chicago Midway Airport. The cheapest flight overall is $130 while the most popular route, (Colorado Springs - Chicago Midway) is currently priced at $278.

  • 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, January is the cheapest month in which you can book a flight from Colorado Springs to Chicago Midway Airport (average of $58). Flying from Colorado Springs to Chicago Midway Airport in July is currently the most expensive (average of $155). 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
Porter
Benton Harbor

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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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$233Average$326FlexibilityNo cancel feeOn-time63%

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