$144+ Cheap flights from Midway (MDW) to Colorado Springs (COS)
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 7/4. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — COS
Jul 21 — Jul 281
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
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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
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Best
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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 June 21, 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 June 21, 2026.
This Southwest deal was found by Cheapflights users on 6/15. 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.
Tue 8/113:35 pm
MDW
- COS
Nonstop2h 25m
Southwest
Tue 8/184:15 pm
COS
- MDW
1 stop5h 35m
Southwest
Deal found 6/15![Southwest logo]()
$281
This Southwest deal was found by Cheapflights users on 6/16. 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 8/253:35 pm
MDW
- COS
Nonstop2h 25m
Southwest
Sat 8/2910:40 am
COS
- MDW
Nonstop2h 20m
Southwest
Deal found 6/16![Southwest logo]()
$283
This Delta deal was found by Cheapflights users on 6/20. 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 8/154:39 pm
MDW
- COS
1 stop5h 59m
Delta
Sat 8/221:20 pm
COS
- MDW
1 stop8h 16m
Delta
Deal found 6/20![Delta logo]()
$291
This Southwest deal was found by Cheapflights users on 6/20. 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 8/155:40 am
MDW
- COS
1 stop6h 20m
Southwest
Mon 8/171:15 pm
COS
- MDW
Nonstop2h 20m
Southwest
Deal found 6/20![Southwest logo]()
$293
This Southwest deal was found by Cheapflights users on 6/16. 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.
Thu 9/176:15 am
MDW
- COS
1 stop11h 15m
Southwest
Tue 9/221:15 pm
COS
- MDW
Nonstop2h 20m
Southwest
Deal found 6/16![Southwest logo]()
$299
This Delta deal was found by Cheapflights users on 6/17. 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 10/216:00 am
MDW
- COS
1 stop7h 58m
Delta
Mon 10/261:40 pm
COS
- MDW
1 stop7h 30m
Delta
Deal found 6/17![Delta logo]()
$303
This Southwest deal was found by Cheapflights users on 6/16. 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.
Sat 8/225:40 am
MDW
- COS
1 stop6h 20m
Southwest
Sat 8/2910:40 am
COS
- MDW
Nonstop2h 20m
Southwest
Deal found 6/16![Southwest logo]()
$305
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 June 21, 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 June 21, 2026.
This Southwest deal was found by Cheapflights users on 6/15. 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 9/23:35 pm
MDW
- COS
Nonstop2h 25m
Southwest
Thu 9/31:15 pm
COS
- MDW
Nonstop2h 20m
Southwest
Deal found 6/15![Southwest logo]()
$283
This Delta deal was found by Cheapflights users on 6/20. 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 8/154:39 pm
MDW
- COS
1 stop5h 59m
Delta
Sat 8/221:20 pm
COS
- MDW
1 stop8h 16m
Delta
Deal found 6/20![Delta logo]()
$291
This Southwest deal was found by Cheapflights users on 6/20. 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 8/152:15 pm
MDW
- COS
2 stops7h 20m
Southwest
Mon 8/171:15 pm
COS
- MDW
Nonstop2h 20m
Southwest
Deal found 6/20![Southwest logo]()
$298
This Southwest deal was found by Cheapflights users on 6/16. 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.
Thu 9/1712:30 pm
MDW
- COS
1 stop8h 25m
Southwest
Tue 9/2210:45 am
COS
- MDW
1 stop5h 25m
Southwest
Deal found 6/16![Southwest logo]()
$308
This Southwest deal was found by Cheapflights users on 6/16. 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 8/48:20 am
MDW
- COS
1 stop5h 20m
Southwest
Sat 8/82:00 pm
COS
- MDW
1 stop7h 15m
Southwest
Deal found 6/16![Southwest logo]()
$326
This Southwest deal was found by Cheapflights users on 6/15. 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.
Mon 7/275:15 am
MDW
- COS
1 stop4h 40m
Southwest
Thu 7/304:55 pm
COS
- MDW
1 stop6h 20m
Southwest
Deal found 6/15![Southwest logo]()
$371
This Southwest deal was found by Cheapflights users on 6/15. 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.
Tue 7/284:05 pm
MDW
- COS
Nonstop2h 30m
Southwest
Sat 8/17:55 pm
COS
- MDW
1 stop8h 30m
Southwest
Deal found 6/15![Southwest logo]()
$376
This Southwest deal was found by Cheapflights users on 6/17. 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.
Sun 8/1610:15 am
MDW
- COS
Nonstop2h 30m
Southwest
Fri 8/281:15 pm
COS
- MDW
Nonstop2h 20m
Southwest
Deal found 6/17![Southwest logo]()
$398
Last-minute flights from Midway to Colorado SpringsDiscover last-minute flight deals from Midway to Colorado Springs. Data last updated June 21, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Colorado Springs. Data last updated June 21, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 6/16. 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.
Sat 7/44:35 pm
MDW
- COS
Nonstop2h 35m
Southwest
Sat 8/17:55 pm
COS
- MDW
1 stop8h 30m
Southwest
Deal found 6/16![Southwest logo]()
$324
This Southwest deal was found by Cheapflights users on 6/16. 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.
Wed 7/85:05 am
MDW
- COS
1 stop5h 50m
Southwest
Tue 7/146:10 pm
COS
- MDW
1 stop5h 00m
Southwest
Deal found 6/16![Southwest logo]()
$341
This Southwest deal was found by Cheapflights users on 6/16. 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.
Thu 7/235:20 am
MDW
- COS
1 stop6h 10m
Southwest
Tue 7/287:05 pm
COS
- MDW
1 stop9h 20m
Southwest
Deal found 6/16![Southwest logo]()
$331
This Southwest deal was found by Cheapflights users on 6/15. 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.
Thu 7/235:15 am
MDW
- COS
1 stop4h 40m
Southwest
Tue 8/41:15 pm
COS
- MDW
Nonstop2h 20m
Southwest
Deal found 6/15![Southwest logo]()
$333
This Southwest deal was found by Cheapflights users on 6/15. 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.
Thu 7/235:15 am
MDW
- COS
1 stop4h 40m
Southwest
Thu 7/302:40 pm
COS
- MDW
Nonstop2h 20m
Southwest
Deal found 6/15![Southwest logo]()
$361
This Southwest deal was found by Cheapflights users on 6/16. 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 7/285:05 am
MDW
- COS
1 stop5h 50m
Southwest
Wed 7/296:10 pm
COS
- MDW
1 stop5h 00m
Southwest
Deal found 6/16![Southwest logo]()
$326
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 June 21, 2026.
Search for one-way flight options from Midway to Colorado Springs. Find affordable one-way fares based on user searches. Data last updated June 21, 2026.
This Southwest deal was found by Cheapflights users on 6/18. 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 7/44:35 pm
MDW
- COS
Nonstop2h 35m
Southwest
Deal found 6/18![Southwest logo]()
$144
This Delta deal was found by Cheapflights users on 6/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/161:00 pm
MDW
- COS
1 stop7h 36m
Delta
Deal found 6/16![Delta logo]()
$146
This Southwest deal was found by Cheapflights users on 6/18. 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 9/153:35 pm
MDW
- COS
Nonstop2h 25m
Southwest
Deal found 6/18![Southwest logo]()
$148
This Delta deal was found by Cheapflights users on 6/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:05 am
MDW
- COS
1 stop7h 10m
Delta
Deal found 6/16![Delta logo]()
$158
This Southwest deal was found by Cheapflights users on 6/18. 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 7/255:40 pm
MDW
- COS
Nonstop2h 35m
Southwest
Deal found 6/18![Southwest logo]()
$176
This Delta deal was found by Cheapflights users on 6/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/116:05 am
MDW
- COS
1 stop7h 10m
Delta
Deal found 6/16![Delta logo]()
$181
This Southwest deal was found by Cheapflights users on 6/17. 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 7/315:15 am
MDW
- COS
1 stop4h 40m
Southwest
Deal found 6/17![Southwest logo]()
$186
This Southwest deal was found by Cheapflights users on 6/17. 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 7/244:35 pm
MDW
- COS
1 stop9h 50m
Southwest
Deal found 6/17![Southwest logo]()
$191
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 June 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $281 (Southwest) |
One-way from | $144 (Southwest) |
Popular in | September |
Cheapest in | April |
Average price | $427 |
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 2,558,603 searches. Data last updated June 21, 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
Quickest round-trip
ChicagoColorado Springs
MDW - COS
MDWCOS
Chicago Midway
Wed 9/2
3:35 pm-5:00 pm
Nonstop2h 25m
Colorado Springs
Thu 9/3
1:15 pm-4:35 pm
Nonstop2h 20m
$283
ChicagoColorado Springs
MDW - COS
MDWCOS
Chicago Midway
Sat 8/15
4:39 pm-9:38 pm
1 stop5h 59m
Colorado Springs
Sat 8/22
1:20 pm-10:36 pm
1 stop8h 16m
$291
ChicagoColorado Springs
MDW - COS
MDWCOS
Chicago Midway
Sat 8/15
2:15 pm-8:35 pm
2 stops7h 20m
Colorado Springs
Mon 8/17
1:15 pm-4:35 pm
Nonstop2h 20m
$298
ChicagoColorado Springs
MDW - COS
MDWCOS
Chicago Midway
Thu 9/17
12:30 pm-7:55 pm
1 stop8h 25m
Colorado Springs
Tue 9/22
10:45 am-5:10 pm
1 stop5h 25m
$308
ChicagoColorado Springs
MDW - COS
MDWCOS
Chicago Midway
Tue 8/4
8:20 am-12:40 pm
1 stop5h 20m
Colorado Springs
Sat 8/8
2:00 pm-10:15 pm
1 stop7h 15m
$326
ChicagoColorado Springs
MDW - COS
MDWCOS
Chicago Midway
Mon 7/27
5:15 am-8:55 am
1 stop4h 40m
Colorado Springs
Thu 7/30
4:55 pm-12:15 am
1 stop6h 20m
$371
ChicagoColorado Springs
MDW - COS
MDWCOS
Chicago Midway
Tue 7/28
4:05 pm-5:35 pm
Nonstop2h 30m
Colorado Springs
Sat 8/1
7:55 pm-5:25 am
1 stop8h 30m
$376
ChicagoColorado Springs
MDW - COS
MDWCOS
Chicago Midway
Sun 8/16
10:15 am-11:45 am
Nonstop2h 30m
Colorado Springs
Fri 8/28
1:15 pm-4:35 pm
Nonstop2h 20m
$398
Cheapest one-way
ChicagoColorado Springs
MDW - COS
MDWCOS
Chicago Midway
Wed 8/19
6:05 am-12:15 pm
1 stop7h 10m
$146
ChicagoColorado Springs
MDW - COS
MDWCOS
Chicago Midway
Wed 9/16
1:55 pm-8:10 pm
1 stop7h 15m
$146
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 June.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 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 June 21, 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.
Food
7.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Comfort
8.0
Overall
7.9
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Comfort
8.0
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.
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.
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Complete your trip
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Alternative routes for Midway to Colorado Springs
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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 June 21, 2026.
Complete your trip
Complete your trip to Colorado Springs by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Midway to Colorado Springs by cabin class
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 June 21, 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 June 21, 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 2,558,603 searches. Data last updated June 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$239 | Average$453 | FlexibilityNo cancel fee | On-time63% |