$137+ Cheap flights from Midway (MDW) to Colorado Springs (COS)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/17. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — COS
Nov 30 — Dec 71
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Colorado Springs 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 Midway to Colorado Springs
Cheapest
Best
Last-minute
One-way
Cheapest flights from Midway to Colorado SpringsExplore 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 October 31, 2026.
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 October 31, 2026.
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.
Mon 12/76:00 am -
1 stop7h 33m
Thu 12/101:40 pm -
1 stop8h 14m
Deal found 10/29![Delta logo]()
$273
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.
Thu 11/266:00 am -
2 stops12h 28m
Thu 12/31:40 pm -
1 stop8h 14m
Deal found 10/29![Delta logo]()
$278
This Southwest deal was found by Cheapflights users on 10/27. 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 12/158:50 am -
2 stops9h 10m
Thu 12/175:50 am -
2 stops8h 10m
Deal found 10/27![Southwest logo]()
$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.
Wed 12/96:00 am -
1 stop7h 33m
Tue 1/121:29 pm -
1 stop7h 48m
Deal found 10/28![Delta logo]()
$301
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.
Wed 12/98:50 am -
2 stops7h 45m
Tue 1/126:05 am -
1 stop9h 25m
Deal found 10/28![Southwest logo]()
$306
This Southwest deal was found by Cheapflights users on 10/26. 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 11/216:10 pm -
Nonstop2h 40m
Wed 11/255:15 pm -
1 stop6h 00m
Deal found 10/26![Southwest logo]()
$308
Best flights from Midway to Colorado SpringsDiscover carefully curated flight deals from Midway to Colorado Springs that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 31, 2026.
Discover carefully curated flight deals from Midway to Colorado Springs that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 31, 2026.
This Southwest deal was found by Cheapflights users on 10/27. 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 12/158:50 am -
2 stops9h 10m
Thu 12/175:50 am -
2 stops8h 10m
Deal found 10/27![Southwest logo]()
$283
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/76:00 am -
1 stop7h 33m
Thu 12/101:40 pm -
1 stop8h 14m
Deal found 10/30![Delta logo]()
$327
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.
Sat 11/214:50 pm -
1 stop6h 05m
Wed 11/255:15 pm -
1 stop6h 00m
Deal found 10/30![Southwest logo]()
$345
This Southwest deal was found by Cheapflights users on 10/27. 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.
Thu 12/245:05 pm -
1 stop5h 40m
Mon 12/285:25 am -
2 stops8h 05m
Deal found 10/27![Southwest logo]()
$371
This Delta deal was found by Cheapflights users on 10/26. 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.
Tue 11/246:00 am -
1 stop7h 26m
Wed 12/21:40 pm -
1 stop8h 14m
Deal found 10/26![Delta logo]()
$426
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.
Mon 11/235:55 am -
1 stop4h 30m
Fri 11/275:05 pm -
1 stop5h 50m
Deal found 10/28![Southwest logo]()
$377
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 12/1811:05 am -
Nonstop2h 30m
Sun 12/204:35 pm -
1 stop4h 45m
Deal found 10/28![Southwest logo]()
$432
Last-minute flights from Midway to Colorado SpringsDiscover last-minute flight deals from Midway to Colorado Springs. Data last updated October 31, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Colorado Springs. Data last updated October 31, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 10/27. 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.
Fri 11/205:55 am -
1 stop4h 30m
Sun 11/227:45 pm -
1 stop9h 00m
Deal found 10/27![Southwest logo]()
$358
This Southwest deal was found by Cheapflights users on 10/26. 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 11/216:10 pm -
Nonstop2h 40m
Wed 11/255:15 pm -
1 stop6h 00m
Deal found 10/26![Southwest logo]()
$308
This Delta deal was found by Cheapflights users on 10/26. 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.
Wed 11/251:05 pm -
1 stop8h 45m
Thu 12/31:40 pm -
1 stop8h 14m
Deal found 10/26![Delta logo]()
$366
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 11/266:00 am -
1 stop7h 50m
Thu 12/34:15 pm -
1 stop4h 15m
Deal found 10/28![Southwest logo]()
$273
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.
Thu 11/266:00 am -
2 stops12h 28m
Thu 12/31:40 pm -
1 stop8h 14m
Deal found 10/29![Delta logo]()
$278
One-way flights from Midway to Colorado SpringsSearch for one-way flight options from Midway to Colorado Springs. Find affordable one-way fares based on user searches. Data last updated October 31, 2026.
Search for one-way flight options from Midway to Colorado Springs. Find affordable one-way fares based on user searches. Data last updated October 31, 2026.
This Southwest deal was found by Cheapflights users on 10/27. 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.
Thu 12/175:55 am -
1 stop4h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Southwest logo]()
$137
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.
Thu 11/266:00 am -
2 stops12h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Delta logo]()
$142
This Southwest deal was found by Cheapflights users on 10/27. 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.
Fri 11/205:55 am -
1 stop4h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Southwest logo]()
$157
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.
Thu 11/267:55 am -
1 stop5h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Southwest logo]()
$164
This Southwest deal was found by Cheapflights users on 10/27. 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.
Fri 1/16:05 am -
1 stop4h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Southwest logo]()
$165
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.
Tue 11/2411:05 am -
Nonstop2h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Southwest logo]()
$187
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.
Mon 12/216:30 pm -
1 stop4h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Southwest logo]()
$197
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.
Sun 12/206:00 am -
1 stop7h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Delta logo]()
$202
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/249:09 am -
2 stops24h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Multiple Airlines logo]()
$208
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1112:27 pm -
2 stops29h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Multiple Airlines logo]()
$217
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 12/255:05 pm -
1 stop5h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Southwest logo]()
$221
Find 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 October 31, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $273 (Delta) |
One-way from | $137 (Southwest) |
Popular in | March |
Cheapest in | April |
Average price | $438 |
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 7,457,451 searches. Data last updated October 31, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Colorado Springs that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoColorado Springs
MDW Chicago Midway - COS Colorado Springs
MDWCOS
Chicago Midway
Thu 11/26
6:00 am-5:28 pm
2 stops12h 28m
Colorado Springs
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$142
ChicagoColorado Springs
MDW Chicago Midway - COS Colorado Springs
MDWCOS
Chicago Midway
Thu 11/26
7:55 am-12:50 pm
1 stop5h 55m
Colorado Springs
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$164
ChicagoColorado Springs
MDW Chicago Midway - COS Colorado Springs
MDWCOS
Chicago Midway
Fri 1/1
6:05 am-9:40 am
1 stop4h 35m
Colorado Springs
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$165
ChicagoColorado Springs
MDW Chicago Midway - COS Colorado Springs
MDWCOS
Chicago Midway
Thu 12/17
5:20 pm-9:50 pm
2 stops5h 30m
Colorado Springs
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$187
ChicagoColorado Springs
MDW Chicago Midway - COS Colorado Springs
MDWCOS
Chicago Midway
Fri 12/25
5:05 pm-9:45 pm
1 stop5h 40m
Colorado Springs
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$221
Quickest round-trip
ChicagoColorado Springs
MDW Chicago Midway - COS Colorado Springs
MDWCOS
Chicago Midway
Tue 11/24
6:00 am-9:20 am
1 stop4h 20m
Colorado Springs
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$231
ChicagoColorado Springs
MDW Chicago Midway - COS Colorado Springs
MDWCOS
Chicago Midway
Fri 11/27
5:20 am-10:25 am
1 stop6h 05m
Colorado Springs
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$231
ChicagoColorado Springs
MDW Chicago Midway - COS Colorado Springs
MDWCOS
Chicago Midway
Fri 11/20
10:00 am-8:00 pm
2 stops11h 00m
Colorado Springs
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$236
ChicagoColorado Springs
MDW Chicago Midway - COS Colorado Springs
MDWCOS
Chicago Midway
Thu 11/12
2:30 pm-9:45 pm
1 stop8h 15m
Colorado Springs
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$262
ChicagoColorado Springs
MDW Chicago Midway - COS Colorado Springs
MDWCOS
Chicago Midway
Fri 11/13
5:55 am-9:25 am
1 stop4h 30m
Colorado Springs
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$262
Showing 1-10 of 17 resultsSorted by cheapest first
Compare providers for flights from Midway to Colorado Springs
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 Midway to Colorado Springs in October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago Midway Airport-Colorado Springs flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Colorado Springs flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Colorado Springs flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago Midway Airport-Colorado Springs 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 Chicago Midway Airport-Colorado Springs 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 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.
MDW-COS
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
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 October 31, 2026.
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.
Boarding
8.1
Crew
8.6
Comfort
8.0
Food
7.0
Entertainment
7.4
Overall
7.9
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Crew
8.6
Comfort
8.0
Food
7.0
Entertainment
7.4
Overall
7.9
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
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.
Traveling to a place near Colorado Springs?
Book flights to Colorado Springs if you plan to visit one of these locationsCañon City
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Other flights to Colorado Springs
Explore flights to Colorado Springs departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on October 31, 2026.
Complete your trip
Complete your trip to Colorado Springs by adding a car rental and/or hotel reservation to your travel itinerary.
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Find flights from Midway to Colorado Springs, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Midway and Colorado Springs flights
Browse other Midway and Colorado Springs flight options. Last updated on October 31, 2026.
Other flights from Midway
Browse through other flights departing from Midway. Flights are based on user searches made on Cheapflights and were last updated on October 31, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 7,457,451 searches. Data last updated October 31, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$326 | Average$438 | FlexibilityNo cancel fee | On-time63% |