$119+ 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 9/9. Fares are subject to change and may not be available on all flights or dates of travel.
COS — MDW
Jul 16 — Jul 231
Round-trip
1 adult, Economy
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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
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Best
Last-minute
One-way
Cheapest flights from Colorado Springs to MidwayExplore 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 June 16, 2026.
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 June 16, 2026.
This Delta deal was found by Cheapflights users on 6/11. 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 8/2511:27 am
COS
- MDW
1 stop5h 34m
Delta
Sat 8/296:05 am
MDW
- COS
1 stop7h 10m
Delta
Deal found 6/11![Delta logo]()
$267
This Southwest deal was found by Cheapflights users on 6/13. 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 9/296:15 am
COS
- MDW
1 stop4h 45m
Southwest
Tue 10/63:40 pm
MDW
- COS
Nonstop2h 35m
Southwest
Deal found 6/13![Southwest logo]()
$277
This Delta deal was found by Cheapflights users on 6/13. 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 9/301:19 pm
COS
- MDW
1 stop8h 06m
Delta
Wed 10/76:00 am
MDW
- COS
1 stop7h 58m
Delta
Deal found 6/13![Delta logo]()
$291
This Southwest deal was found by Cheapflights users on 6/14. 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 7/156:10 pm
COS
- MDW
1 stop5h 00m
Southwest
Wed 7/2910:15 am
MDW
- COS
2 stops10h 00m
Southwest
Deal found 6/14![Southwest logo]()
$296
This Southwest deal was found by Cheapflights users on 6/13. 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 8/41:15 pm
COS
- MDW
Nonstop2h 20m
Southwest
Sat 8/86:45 am
MDW
- COS
1 stop7h 35m
Southwest
Deal found 6/13![Southwest logo]()
$305
This Southwest deal was found by Cheapflights users on 6/13. 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 10/37:30 am
COS
- MDW
Nonstop2h 20m
Southwest
Tue 10/63:40 pm
MDW
- COS
Nonstop2h 35m
Southwest
Deal found 6/13![Southwest logo]()
$306
This Southwest deal was found by Cheapflights users on 6/11. 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 7/145:35 am
COS
- MDW
1 stop4h 30m
Southwest
Wed 7/1512:00 pm
MDW
- COS
1 stop8h 15m
Southwest
Deal found 6/11![Southwest logo]()
$307
This Southwest deal was found by Cheapflights users on 6/13. 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 7/287:05 pm
COS
- MDW
1 stop9h 20m
Southwest
Wed 8/124:40 pm
MDW
- COS
2 stops6h 05m
Southwest
Deal found 6/13![Southwest logo]()
$308
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.
Sat 8/2210:40 am
COS
- MDW
Nonstop2h 20m
Southwest
Sat 8/296:45 am
MDW
- COS
2 stops9h 45m
Southwest
Deal found 6/15![Southwest logo]()
$310
Best flights from Colorado Springs to MidwayDiscover carefully curated flight deals from Colorado Springs to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 16, 2026.
Discover carefully curated flight deals from Colorado Springs to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 16, 2026.
This Delta deal was found by Cheapflights users on 6/13. 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 9/261:19 pm
COS
- MDW
1 stop8h 06m
Delta
Sat 10/36:05 am
MDW
- COS
1 stop7h 09m
Delta
Deal found 6/13![Delta logo]()
$315
This Southwest deal was found by Cheapflights users on 6/11. 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 7/145:35 am
COS
- MDW
2 stops5h 50m
Southwest
Wed 7/1510:15 am
MDW
- COS
2 stops10h 00m
Southwest
Deal found 6/11![Southwest logo]()
$317
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 10/810:15 am
COS
- MDW
1 stop12h 30m
Southwest
Sat 10/101:55 pm
MDW
- COS
1 stop4h 20m
Southwest
Deal found 6/15![Southwest logo]()
$320
This Southwest deal was found by Cheapflights users on 6/13. 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 9/291:15 pm
COS
- MDW
2 stops8h 05m
Southwest
Tue 10/63:15 pm
MDW
- COS
2 stops7h 00m
Southwest
Deal found 6/13![Southwest logo]()
$336
This Delta deal was found by Cheapflights users on 6/13. 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 10/11:19 pm
COS
- MDW
1 stop8h 06m
Delta
Wed 10/76:00 am
MDW
- COS
1 stop7h 58m
Delta
Deal found 6/13![Delta logo]()
$375
This Southwest deal was found by Cheapflights users on 6/14. 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 7/155:35 am
COS
- MDW
2 stops7h 20m
Southwest
Wed 7/2910:15 am
MDW
- COS
2 stops10h 00m
Southwest
Deal found 6/14![Southwest logo]()
$336
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.
Fri 9/45:30 am
COS
- MDW
2 stops10h 30m
Southwest
Mon 9/75:55 am
MDW
- COS
1 stop8h 40m
Southwest
Deal found 6/15![Southwest logo]()
$348
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 7/234:55 pm
COS
- MDW
2 stops7h 10m
Southwest
Wed 7/2910:15 am
MDW
- COS
2 stops10h 00m
Southwest
Deal found 6/15![Southwest logo]()
$361
This Southwest deal was found by Cheapflights users on 6/13. 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 7/1612:20 pm
COS
- MDW
1 stop10h 10m
Southwest
Tue 7/2110:15 am
MDW
- COS
2 stops10h 00m
Southwest
Deal found 6/13![Southwest logo]()
$371
This Southwest deal was found by Cheapflights users on 6/11. 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 8/88:55 am
COS
- MDW
2 stops7h 10m
Southwest
Sun 8/96:05 am
MDW
- COS
1 stop5h 15m
Southwest
Deal found 6/11![Southwest logo]()
$371
This Southwest deal was found by Cheapflights users on 6/12. 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 7/109:35 am
COS
- MDW
1 stop8h 30m
Southwest
Sat 7/115:40 pm
MDW
- COS
Nonstop2h 35m
Southwest
Deal found 6/12![Southwest logo]()
$381
Last-minute flights from Colorado Springs to MidwayDiscover last-minute flight deals from Colorado Springs to Midway. Data last updated June 16, 2026 and is based on user searches.
Discover last-minute flight deals from Colorado Springs to Midway. Data last updated June 16, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 6/11. 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 7/47:05 am
COS
- MDW
Nonstop2h 20m
Southwest
Tue 7/74:35 pm
MDW
- COS
1 stop6h 15m
Southwest
Deal found 6/11![Southwest logo]()
$339
This Southwest deal was found by Cheapflights users on 6/11. 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 7/145:35 am
COS
- MDW
1 stop4h 30m
Southwest
Wed 7/1512:00 pm
MDW
- COS
1 stop8h 15m
Southwest
Deal found 6/11![Southwest logo]()
$307
This Southwest deal was found by Cheapflights users on 6/12. 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 7/145:35 am
COS
- MDW
2 stops5h 50m
Southwest
Mon 7/205:15 am
MDW
- COS
1 stop4h 40m
Southwest
Deal found 6/12![Southwest logo]()
$336
This Southwest deal was found by Cheapflights users on 6/14. 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 7/156:10 pm
COS
- MDW
1 stop5h 00m
Southwest
Wed 7/294:35 pm
MDW
- COS
1 stop6h 15m
Southwest
Deal found 6/14![Southwest logo]()
$291
This Southwest deal was found by Cheapflights users on 6/14. 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.
Sat 7/259:25 am
COS
- MDW
Nonstop2h 25m
Southwest
Tue 7/285:05 am
MDW
- COS
1 stop5h 50m
Southwest
Deal found 6/14![Southwest logo]()
$321
This Southwest deal was found by Cheapflights users on 6/13. 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 7/286:10 pm
COS
- MDW
1 stop5h 00m
Southwest
Tue 8/46:40 am
MDW
- COS
1 stop4h 10m
Southwest
Deal found 6/13![Southwest logo]()
$303
This Southwest deal was found by Cheapflights users on 6/13. 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 7/287:05 pm
COS
- MDW
1 stop9h 20m
Southwest
Wed 8/124:40 pm
MDW
- COS
2 stops6h 05m
Southwest
Deal found 6/13![Southwest logo]()
$308
One-way flights from Colorado Springs to MidwaySearch for one-way flight options from Colorado Springs to Midway. Find affordable one-way fares based on user searches. Data last updated June 16, 2026.
Search for one-way flight options from Colorado Springs to Midway. Find affordable one-way fares based on user searches. Data last updated June 16, 2026.
This Southwest deal was found by Cheapflights users on 6/12. 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 9/910:45 am
COS
- MDW
1 stop7h 25m
Southwest
Deal found 6/12![Southwest logo]()
$119
This Delta deal was found by Cheapflights users on 6/11. 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 8/1111:27 am
COS
- MDW
1 stop5h 34m
Delta
Deal found 6/11![Delta logo]()
$122
This Southwest deal was found by Cheapflights users on 6/11. 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 12/812:00 pm
COS
- MDW
2 stops8h 30m
Southwest
Deal found 6/11![Southwest logo]()
$124
This Delta deal was found by Cheapflights users on 6/11. 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 9/96:00 am
COS
- MDW
2 stops11h 05m
Delta
Deal found 6/11![Delta logo]()
$127
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 8/121:15 pm
COS
- MDW
Nonstop2h 20m
Southwest
Deal found 6/15![Southwest logo]()
$136
This Southwest deal was found by Cheapflights users on 6/11. 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 7/47:05 am
COS
- MDW
Nonstop2h 20m
Southwest
Deal found 6/11![Southwest logo]()
$144
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/91:40 pm
COS
- MDW
1 stop7h 30m
Delta
Deal found 6/15![Delta logo]()
$146
This Southwest deal was found by Cheapflights users on 6/14. 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.
Tue 8/111:15 pm
COS
- MDW
Nonstop2h 20m
Southwest
Deal found 6/14![Southwest logo]()
$148
This Delta deal was found by Cheapflights users on 6/11. 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 7/46:50 am
COS
- MDW
1 stop7h 50m
Delta
Deal found 6/11![Delta logo]()
$154
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:00 am
COS
- MDW
1 stop8h 25m
Delta
Deal found 6/15![Delta logo]()
$158
Find 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 June 16, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $267 (Delta) |
One-way from | $119 (Southwest) |
Popular in | November |
Cheapest in | April |
Average price | $483 |
Good round-trip deal | $402 or less |
Good one-way deal | $223 or less |
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 June 16, 2026.
Use the filters below to find and compare flights from Colorado Springs to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Colorado SpringsChicago
COS - MDW
COSMDW
Colorado Springs
Sat 9/26
1:19 pm-10:25 pm
1 stop8h 06m
Chicago Midway
Sat 10/3
6:05 am-12:14 pm
1 stop7h 09m
$315
Colorado SpringsChicago
COS - MDW
COSMDW
Colorado Springs
Tue 7/14
5:35 am-12:25 pm
2 stops5h 50m
Chicago Midway
Wed 7/15
10:15 am-7:15 pm
2 stops10h 00m
$317
Colorado SpringsChicago
COS - MDW
COSMDW
Colorado Springs
Thu 10/8
10:15 am-11:45 pm
1 stop12h 30m
Chicago Midway
Sat 10/10
1:55 pm-5:15 pm
1 stop4h 20m
$320
Colorado SpringsChicago
COS - MDW
COSMDW
Colorado Springs
Tue 9/29
1:15 pm-10:20 pm
2 stops8h 05m
Chicago Midway
Tue 10/6
3:15 pm-9:15 pm
2 stops7h 00m
$336
Colorado SpringsChicago
COS - MDW
COSMDW
Colorado Springs
Wed 7/15
5:35 am-1:55 pm
2 stops7h 20m
Chicago Midway
Wed 7/29
10:15 am-7:15 pm
2 stops10h 00m
$336
Colorado SpringsChicago
COS - MDW
COSMDW
Colorado Springs
Fri 9/4
5:30 am-5:00 pm
2 stops10h 30m
Chicago Midway
Mon 9/7
5:55 am-1:35 pm
1 stop8h 40m
$348
Colorado SpringsChicago
COS - MDW
COSMDW
Colorado Springs
Thu 7/23
4:55 pm-1:05 am
2 stops7h 10m
Chicago Midway
Wed 7/29
10:15 am-7:15 pm
2 stops10h 00m
$361
Colorado SpringsChicago
COS - MDW
COSMDW
Colorado Springs
Thu 7/16
12:20 pm-11:30 pm
1 stop10h 10m
Chicago Midway
Tue 7/21
10:15 am-7:15 pm
2 stops10h 00m
$371
Colorado SpringsChicago
COS - MDW
COSMDW
Colorado Springs
Sat 8/8
8:55 am-5:05 pm
2 stops7h 10m
Chicago Midway
Sun 8/9
6:05 am-10:20 am
1 stop5h 15m
$371
Colorado SpringsChicago
COS - MDW
COSMDW
Colorado Springs
Thu 10/1
1:19 pm-10:25 pm
1 stop8h 06m
Chicago Midway
Wed 10/7
6:00 am-12:58 pm
1 stop7h 58m
$375
Showing 1-10 of 22 resultsSorted by cheapest first
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 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 Colorado Springs-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Colorado Springs-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >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 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 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.
COS-MDW
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 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 June 16, 2026.
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.
How much does it cost to fly round-trip from Colorado Springs to Chicago Midway Airport?
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 June 16, 2026.
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.
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
7.9
Crew
8.6
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
7.9
Crew
8.6
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
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.
Traveling to a place near Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Hammond
Porter
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Other flights to Midway
Explore flights to Midway departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on June 16, 2026.
Colorado Springs and Midway flights
Browse other Colorado Springs and Midway flight options. Last updated on June 16, 2026.
Other flights from Colorado Springs
Browse through other flights departing from Colorado Springs. Flights are based on user searches made on Cheapflights and were last updated on June 16, 2026.
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Check out other popular destinations found by fellow travelers in 2026
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 June 16, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$227 | Average$371 | FlexibilityNo cancel fee | On-time63% |