COS - MDW

$122 Find Cheap Flights from Colorado Springs to Chicago Midway Airport - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Colorado Springs to Midway departing on 8/27. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$243
Typical prices: $317-$385
Southwest
Mon 8/24Wed 8/26
COS - MDW • Non-stop
Cheapest one-way
$122
Southwest
Thu 8/27
COS - MDW • Non-stop
Top airlines
Southwest
Cheapest • from $243 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Every day
You can fly direct with Southwest. Average duration is 2h 20m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top layover airports
Dallas (DAL)
Cheapest • Avg $334 (round-trip)
Denver (DEN)
Shortest trip • 4h 36m (one-way)
Insights
Insights
Insights
Insights
When to travel
April
Cheapest • 32% price drop
September
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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We hope you love your trip to Midway!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Colorado Springs to Midway (COS-MDW)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Colorado Springs to Midway that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Colorado Springs to Midway

Mon, Aug 24 - Wed, Aug 26
Southwest Logo
1:15 pm - 4:35 pm
COS
-
MDW
2h 20mnonstop
Southwest Logo
3:35 pm - 5:00 pm
MDW
-
COS
2h 25mnonstop
$243Southwest
Tue, Aug 25 - Tue, Sep 1
Southwest Logo
1:15 pm - 4:35 pm
COS
-
MDW
2h 20mnonstop
Southwest Logo
3:35 pm - 5:00 pm
MDW
-
COS
2h 25mnonstop
$243Southwest
Tue, Oct 27 - Fri, Oct 30
Southwest Logo
12:40 pm - 4:00 pm
COS
-
MDW
2h 20mnonstop
Southwest Logo
11:50 am - 1:25 pm
MDW
-
COS
2h 35mnonstop
$248Southwest
Tue, Aug 25 - Tue, Sep 1
Southwest Logo
6:15 am - 12:00 pm
COS
-
MDW
4h 45m
1 stop
Southwest Logo
3:35 pm - 5:00 pm
MDW
-
COS
2h 25mnonstop
$249Southwest
Mon, Aug 24 - Wed, Aug 26
Southwest Logo
1:15 pm - 4:35 pm
COS
-
MDW
2h 20mnonstop
Southwest Logo
3:35 pm - 5:00 pm
MDW
-
COS
2h 25mnonstop
$252Southwest
Mon, Aug 24 - Wed, Aug 26
Southwest Logo
4:20 pm - 10:00 pm
COS
-
MDW
4h 40m
1 stop
Southwest Logo
3:35 pm - 5:00 pm
MDW
-
COS
2h 25mnonstop
$253Southwest
Wed, Oct 14 - Tue, Oct 20
Southwest Logo
12:40 pm - 4:00 pm
COS
-
MDW
2h 20mnonstop
Southwest Logo
2:50 pm - 7:50 pm
MDW
-
COS
6h 00m
1 stop
$253Southwest
Sat, Sep 26 - Tue, Sep 29
Southwest Logo
12:15 pm - 7:15 pm
COS
-
MDW
6h 00m
1 stop
Southwest Logo
3:35 pm - 5:00 pm
MDW
-
COS
2h 25mnonstop
$253Southwest
Tue, Jan 5 - Wed, Jan 13
Delta Logo
1:40 pm - 10:10 pm
COS
-
MDW
7h 30m
1 stop
Delta Logo
6:00 am - 12:58 pm
MDW
-
COS
7h 58m
1 stop
$263Delta
Wed, Jan 6 - Sat, Jan 9
Delta Logo
1:40 pm - 10:10 pm
COS
-
MDW
7h 30m
1 stop
Delta Logo
6:00 am - 12:58 pm
MDW
-
COS
7h 58m
1 stop
$263Delta
Booking Insights

KAYAK's insights & trends for Colorado Springs to Midway flights

Get data-powered insights and trends into flights from Colorado Springs to Midway to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Colorado Springs to Chicago Midway Airport?

The average price of all round-trip flights from Colorado Springs to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Colorado Springs to Chicago Midway Airport, look for departures on Thursdays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from Chicago Midway Airport, Friday is the cheapest day to fly and Thursday is the most expensive.

What is the cheapest month to fly from Colorado Springs to Chicago Midway Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Colorado Springs to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Colorado Springs to Chicago Midway Airport is April, where tickets cost $288 (return) on average. On the other hand, the most expensive months are March and November, where the average cost of round-trip tickets is $671 and $544 respectively.

Can I save money by flying with a layover from Colorado Springs to Chicago Midway Airport?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $351 on average.

Find deals

Good to know

Low season

February

Cheapest flight

$122
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly and prices are also 16% lower on average.
Flight from Colorado Springs to Chicago Midway Airport

When to book flights from Colorado Springs to Midway

Are your dates flexible? Find out the best times to travel from Colorado Springs to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Colorado Springs to Chicago Midway Airport flights

  • What is the cheapest flight from Colorado Springs to Chicago Midway Airport?

    In the last 5 days, the lowest price for a flight from Colorado Springs to Chicago Midway Airport was $122 for a one-way ticket and $243 for a round-trip.

  • Do I need a passport to fly between Colorado Springs and Chicago Midway Airport?

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

  • Which airlines offer Wi-Fi service onboard planes from Colorado Springs to Chicago Midway Airport?

    American Airlines, and Delta offer inflight Wi-Fi service on the Colorado Springs to Chicago Midway Airport flight route.

  • Which aircraft models fly most regularly from Colorado Springs to Chicago Midway Airport?

    The Boeing 737 MAX 8 is the aircraft model that flies most regularly on the Colorado Springs to Chicago Midway Airport flight route.

  • On which days can I fly direct from Colorado Springs to Chicago Midway Airport?

    There are nonstop flights from Colorado Springs to Chicago Midway Airport on a daily basis.

  • How does KAYAK find such low prices on flights from Colorado Springs to Chicago Midway Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Colorado Springs to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Colorado Springs to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Colorado Springs is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Colorado Springs to Chicago Midway Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago Midway Airport with an airline and back to Colorado Springs with another airline. Booking your flights between Colorado Springs and MDW can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Colorado Springs to Chicago Midway Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport from Colorado Springs up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Colorado Springs to Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $216 or less one-way and $361 or less round-trip.

Prefer to fly direct from Colorado Springs to Chicago Midway Airport?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Colorado Springs to Chicago Midway.
Find which airlines fly direct from Colorado Springs Airport to Chicago Midway Airport, which days they fly and book direct flights.

Direct departures

Colorado Springs to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Chicago Midway to Colorado Springs

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Reviews of the top airline flying from Colorado Springs to Midway

 
See real verified KAYAK customer reviews for airlines flying from Colorado Springs to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Colorado Springs to Midway? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4227 reviews
8.1Boarding
8.0Comfort
8.6Crew
7.5Entertainment
7.0Food
Airline reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

2.0 MediocreMatthew, Jun 2026
CVG - MDW
Read more Southwest reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

Great flight. I didn't get a drink because I was asleep whole on the flight.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

WiFi was not working and didn’t have a beverage service

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Delay after delay after delay. Very disappointing I am about ready to give up on Southwest. One of the crewmembers sat and played games on her phone for the entire trip from Chicago to Baltimore. Unbelievable, very unprofessional, and very disappointing.

Everything you need to know for your flight from Colorado Springs to Midway

Information on your arrival and departure airports

Colorado Springs (COS)
Midway (MDW)