MDW - COS

$126 Find Cheap Flights from Chicago Midway Airport to Colorado Springs

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Colorado Springs departing on 8/9. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Colorado Springs

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

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

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Colorado Springs 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 Midway to Colorado Springs

Sat, Aug 9 - Mon, Aug 11
Southwest Logo
5:35 pm - 7:05 pmMDW-COS
2h 30mnonstop
Southwest Logo
7:10 am - 2:30 pmCOS-MDW
6h 20m1 stop
$263Southwest
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Sat, Aug 9 - Mon, Aug 11
Southwest Logo
5:35 pm - 7:05 pmMDW-COS
2h 30mnonstop
Southwest Logo
6:25 am - 2:45 pmCOS-MDW
7h 20m2 stops
$268Southwest
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Fri, Aug 8 - Mon, Aug 11
Southwest Logo
7:45 am - 9:10 amMDW-COS
2h 25mnonstop
Southwest Logo
7:10 am - 2:30 pmCOS-MDW
6h 20m1 stop
$293Southwest
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Mon, Aug 25 - Fri, Aug 29
Delta Logo
6:00 am - 12:12 pmMDW-COS
7h 12m1 stop
Delta Logo
11:11 am - 5:37 pmCOS-MDW
5h 26m1 stop
$294Delta
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Fri, Aug 8 - Mon, Aug 11
Southwest Logo
7:45 am - 9:10 amMDW-COS
2h 25mnonstop
Southwest Logo
6:25 am - 2:45 pmCOS-MDW
7h 20m2 stops
$298Southwest
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Mon, Aug 25 - Fri, Aug 29
Southwest Logo
7:45 am - 9:10 amMDW-COS
2h 25mnonstop
Southwest Logo
4:20 pm - 11:50 pmCOS-MDW
6h 30m1 stop
$303Southwest
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Fri, Aug 1 - Sat, Aug 9
Delta Logo
1:09 pm - 10:13 pmMDW-COS
10h 04m2 stops
Delta Logo
6:00 am - 3:27 pmCOS-MDW
8h 27m1 stop
$306Delta
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Mon, Aug 25 - Fri, Aug 29
Southwest Logo
5:25 am - 9:55 amMDW-COS
5h 30m1 stop
Southwest Logo
6:25 am - 4:40 pmCOS-MDW
9h 15m2 stops
$308Southwest
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Mon, Jul 14 - Fri, Jul 18
Southwest Logo
5:35 pm - 7:10 pmMDW-COS
2h 35mnonstop
Southwest Logo
3:50 pm - 7:15 pmCOS-MDW
2h 25mnonstop
$311Southwest
Find Deal
Sat, Aug 9 - Mon, Aug 11
Southwest Logo
5:35 pm - 7:05 pmMDW-COS
2h 30mnonstop
Southwest Logo
9:45 am - 1:10 pmCOS-MDW
2h 25mnonstop
$312Southwest
Find Deal
Useful Info

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

Get data-powered insights and trends into flights from Midway to Colorado Springs 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 Chicago Midway Airport to Colorado Springs?

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

If your flying dates are flexible, you should consider flying to Colorado Springs on a Tuesday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from Chicago Midway Airport to Colorado Springs. For your return ticket, we recommend flying on a Wednesday and avoiding Sundays for the best deals.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to Colorado Springs, 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 Chicago Midway Airport to Colorado Springs is November, where tickets cost $304 (return) on average. On the other hand, the most expensive months are August and May, where the average cost of round-trip tickets is $778 and $440 respectively.

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

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 1 stop layover the cheapest option at $375 on average.

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Good to know

Low seasonMarch
High seasonDecember
Cheapest flight$126
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly and prices are also 12% lower on average.
Flight from Chicago Midway Airport to Colorado Springs

When to book flights from Midway to Colorado Springs

Are your dates flexible? Find out the best times to travel from Midway to Colorado Springs 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 Chicago Midway Airport to Colorado Springs flights

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

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Colorado Springs was $126 for a one-way ticket and $263 for a round-trip.

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

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

  • Which airports will I be using when flying from Chicago Midway Airport to Colorado Springs?

    On your way to Colorado Springs, you’ll fly out from Chicago Midway. You’ll be landing at Colorado Springs.

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

    Only American Airlines offers inflight Wi-Fi service on the Chicago Midway Airport to Colorado Springs flight route.

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

    The Embraer 175 (Enhanced Winglets) is the aircraft model that flies most regularly on the Chicago Midway Airport to Colorado Springs flight route.

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

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

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

    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 Chicago Midway Airport to Colorado Springs.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Colorado Springs from Chicago Midway Airport 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 Chicago Midway Airport to Colorado Springs?

    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 Colorado Springs with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and COS 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 Chicago Midway Airport to Colorado Springs?

    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 Colorado Springs from Chicago Midway Airport 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 Chicago Midway Airport to Colorado Springs

  • Looking for a cheap flight? 25% of our users found flights on this route for $145 or less one-way and $324 or less round-trip.

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

Find which airlines fly direct from Chicago Midway Airport to Colorado Springs Airport, which days they fly and book direct flights.

Direct departures

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

Direct returns

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
See more direct flights

Top airline flying from Midway to Colorado Springs

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Colorado Springs. 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 Midway to Colorado Springs? 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 4287 reviews
7.1Food
8.2Boarding
8.0Comfort
7.6Entertainment
8.6Crew
Airline reviews

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

6.0 GoodDavid, Jun 2025BWI - COS
Read more Southwest reviews

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

WiFi on the flight was not working. Thus, entertainment options were limited.

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.

For the first time in a long time we had a flawless experience with Southwest. Both flights were early and no mechanical errors at all. We were shocked and pleasantly surprised 😮.

One of the crew performed a hilarious skit to accompany the standard instructions. Passengers enjoyed it so much they applauded at the end!

Excellent experience. WiFi worked on this leg of My trip

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

Information on your arrival and departure airports

Chicago Midway Airport (MDW)
Colorado Springs (COS)

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