COS - MDW

$114 Find Cheap Flights from Colorado Springs to Chicago Midway Airport

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 6/10. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Colorado Springs to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Colorado Springs to Chicago, as well as popular online travel agencies
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Flights Deals

Cheap Flight Deals 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.

Recent round-trip flight deals from Colorado Springs to Midway

KAYAK's recommended round-trip deals from the most popular airlines that fly from Colorado Springs to Midway.
Discover the best prices for you by selecting your travel dates on KAYAK.
Delta Logo
10:54 am - 5:10 pmCOS-MDW
5h 16m1 stop
Delta Logo
6:00 am - 1:27 pmMDW-COS
8h 27m1 stop
$259Delta
Find Deal
Sat, Jul 26 - Tue, Jul 29
Delta Logo
6:00 am - 3:37 pmCOS-MDW
8h 37m1 stop
Delta Logo
1:46 pm - 10:13 pmMDW-COS
9h 27m2 stops
$264Delta
Find Deal
Sat, Jul 26 - Tue, Jul 29
Southwest Logo
3:50 pm - 7:15 pmCOS-MDW
2h 25mnonstop
Southwest Logo
6:55 am - 11:55 amMDW-COS
6h 00m1 stop
$272Southwest
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Fri, Jul 25 - Tue, Jul 29
Southwest Logo
3:50 pm - 7:15 pmCOS-MDW
2h 25mnonstop
Southwest Logo
9:05 am - 4:00 pmMDW-COS
7h 55m2 stops
$277Southwest
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Fri, Jul 25 - Tue, Jul 29
Southwest Logo
2:35 pm - 10:05 pmCOS-MDW
6h 30m1 stop
Southwest Logo
7:20 am - 2:05 pmMDW-COS
7h 45m1 stop
$282Southwest
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Wed, Aug 27 - Fri, Aug 29
Delta Logo
6:00 am - 3:20 pmCOS-MDW
8h 20m1 stop
Delta Logo
9:24 am - 8:57 pmMDW-COS
12h 33m2 stops
$287Delta
Find Deal
Sat, Jun 7 - Tue, Jun 10
Delta Logo
5:55 pm - 8:39 amCOS-MDW
13h 44m2 stops
Delta Logo
1:46 pm - 10:13 pmMDW-COS
9h 27m2 stops
$292Delta
Find Deal
Fri, Jul 25 - Tue, Jul 29
Southwest Logo
3:50 pm - 7:15 pmCOS-MDW
2h 25mnonstop
Southwest Logo
5:25 pm - 7:00 pmMDW-COS
2h 35mnonstop
$297Southwest
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Fri, Jul 25 - Tue, Jul 29
Southwest Logo
6:05 pm - 12:55 amCOS-MDW
5h 50m1 stop
Southwest Logo
5:35 pm - 7:10 pmMDW-COS
2h 35mnonstop
$307Southwest
Find Deal
Fri, Jul 25 - Mon, Jul 28
Southwest Logo
8:25 am - 11:50 amCOS-MDW
2h 25mnonstop
Southwest Logo
7:50 am - 9:30 amMDW-COS
2h 40mnonstop
$311Southwest
Find Deal
Sat, Oct 18 - Sun, Nov 2
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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 Wednesdays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from Chicago Midway Airport, Tuesday is the cheapest day to fly and Saturday 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 July, where tickets cost $280 (return) on average. On the other hand, the most expensive months are April and September, where the average cost of round-trip tickets is $668 and $582 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.

No, with an average price for the route of $213, prices are generally cheapest when you fly direct.

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Good to know

Low seasonJanuary
High seasonOctober
Cheapest flight$114
Best time to beat the crowds with an average 31% drop in price.
Most popular time to fly with an average 11% increase in price.
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 3 days, the lowest price for a flight from Colorado Springs to Chicago Midway Airport was $114 for a one-way ticket and $259 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 Embraer 175 (Enhanced Winglets) 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?

    You can catch a nonstop flight from Colorado Springs to Chicago Midway Airport on Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday.

  • 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 $149 or less one-way and $348 or less round-trip.

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

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
See more direct flights

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 4294 reviews
7.6Entertainment
8.0Comfort
8.2Boarding
8.6Crew
7.1Food
Airline reviews

I would have liked to arrive on time - not 5 hours late!

4.0 OkayAnonymous, Apr 2025DEN - SEA
Read more Southwest reviews

I would have liked to arrive on time - not 5 hours late!

1.5 hour delay, poor service, no compassion from the crew. Terrible experience

Our flight was diverted from being a non-stop to getting within 150 miles and requiring another plane. We heard 4 or 5 different versions from SW as to why we had to stop, then wait for a replacement plane. Five hour delay, weather did not come up as a single excuse.... communication was not clear and well explained. No one really took charge!

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

I really like open seating. I hate that I've heard this is going away. This is one of the unique things that makes Southwest my goto choice.

It seems as though the provisions are even less. Although SWA used to be an economy Airline, that isn't really the case anymore. I paid over $700. for a round trip to Denver and I could have flown just about any airline for the price. The drinks are now in a 6-ounce cup and with ice I'm sure a can would fill more than 2 cups. However, I am very proud of SWA for using paper rather than continuing to contribute to the millions of plastic cups being used each day. I've thought of this fr many years and am so glad to see it come to fruition, if not by only SWA so far.

My original flight was extremely delayed but I was able to join the standby list for an earlier flight. I was grateful for this feature but I wish I could’ve gotten my standby confirmation sooner.

I like that it was on time and the staff was friendly.

No space for our carryon and needed to check at plane before boarding !

Flight was ok. Boarding wasn’t fun. Flights were delayed by 12 minutes on each leg.

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

Information on your arrival and departure airports

Midway (MDW)
Colorado Springs (COS)

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