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COS - MDW

$168 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 6/27. 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
0 bags
Sat 6/29
Sat 7/6

Search 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
In the last 7 days travelers have searched 42,686,544 times on KAYAK, and here is why:

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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.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
11:28 am - 6:38 pmCOS-MDW
6h 10m1 stop
3:45 pm - 8:29 pmMDW-COS
5h 44m1 stop
$313Delta
Find Deal
Sat, Sep 7 - Wed, Sep 11
11:28 am - 9:46 pmCOS-MDW
9h 18m2 stops
3:45 pm - 8:29 pmMDW-COS
5h 44m1 stop
$318Delta
Find Deal
Sat, Sep 7 - Wed, Sep 11
11:28 am - 6:39 pmCOS-MDW
6h 11m1 stop
9:33 am - 10:29 amMDW-COS
25h 56m2 stops
$370Delta
Find Deal
Sat, Jul 13 - Fri, Jul 19
11:35 am - 6:39 pmCOS-MDW
6h 04m1 stop
9:33 am - 9:00 pmMDW-COS
12h 27m2 stops
$374Delta
Find Deal
Tue, Jul 23 - Tue, Aug 6
6:00 am - 6:39 pmCOS-MDW
11h 39m2 stops
9:33 am - 9:00 pmMDW-COS
12h 27m2 stops
$420Delta
Find Deal
Tue, Jul 23 - Tue, Aug 6
6:00 am - 2:57 pmCOS-MDW
7h 57m1 stop
5:45 pm - 10:40 amMDW-COS
17h 55m2 stops
$440Delta
Find Deal
Sat, Jul 13 - Sun, Jul 21
11:28 am - 6:39 pmCOS-MDW
6h 11m1 stop
6:55 pm - 9:00 pmMDW-COS
27h 05m1 stop
$463Delta
Find Deal
Sat, Jul 13 - Fri, Jul 19
11:28 am - 6:39 pmCOS-MDW
6h 11m1 stop
3:47 pm - 9:00 pmMDW-COS
6h 13m1 stop
$469Delta
Find Deal
Sat, Jul 13 - Sat, Jul 20
11:28 am - 6:39 pmCOS-MDW
6h 11m1 stop
9:24 am - 7:36 pmMDW-COS
11h 12m2 stops
$474Delta
Find Deal
Sat, Jul 13 - Sat, Jul 20
11:35 am - 6:39 pmCOS-MDW
6h 04m1 stop
3:47 pm - 9:00 pmMDW-COS
6h 13m1 stop
$498Delta
Find Deal
Tue, Jul 23 - Tue, Aug 6

Flights from Colorado Springs to Midway - Travel Insights & Trends

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.

How many flights are there between Colorado Springs and Chicago Midway Airport per day?

Each day, there are between 1 and 2 nonstop flights that take off from Colorado Springs and land in Chicago Midway Airport, with an average flight time of 2h 20m. The most common departure time is 5:00 am and most flights take off in the afternoon. Each week, there are 12 flights. The most frequent day of departure is Monday, when 17% of all weekly flights depart. The fewest flights depart on a Saturday.

What’s the earliest departure time from Colorado Springs to Chicago Midway Airport?

Early birds can take the earliest flight from Colorado Springs at 5:00 am and will be landing in Chicago Midway Airport at 8:20 am.

What’s the latest departure time from Colorado Springs to Chicago Midway Airport?

If you prefer to fly at night, the latest flight from Colorado Springs to Chicago Midway Airport jets off at 3:10 pm and lands at 6:30 pm.

Good to know

Cheapest flight

$168
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 $168 for a one-way ticket and $313 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 aircraft models fly most regularly from Colorado Springs to Chicago Midway Airport?

    We unfortunately don’t have that data for this specific 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.

See more FAQs

Prefer to fly non-stop from Colorado Springs to Chicago Midway Airport?

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

Nonstop 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

Nonstop 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
DeltaOverall score based on 10457 reviews
8.2Boarding
7.9Comfort
8.6Crew
7.4Food
8.0Entertainment
Airline reviews

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

10.0 ExcellentMichael, May 2024SJC - ATL
Read more about Delta reviews

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

They were an hour late and they didn’t have my wheelchair for me

The Flight crew didn’t serve us until about 1.5 hours into the flight because of turbulence but after it ended it was fine to move around. They served us water only and snacks and then NEVER, NOT ONE TIME came through to collect trash until right before landing about 1.5 hours later. There was absolutely no need for that. They crew was just standing around talking and visiting with each other and really never tried to see if we might want something besides water or even try to come pick up trash. This is VERY unusual for a Delta flight but it was not what I would have expected for a 4 hour flight.

Book cheap flights from Colorado Springs to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Colorado Springs to Chicago found on KAYAK in the last 72 hours.
6/27Thu
2 stops
25h 18mCOS-MDW
$168
10/25Fri
1 stopDelta
7h 14mCOS-MDW
$194
9/25Wed
1 stopDelta
7h 11mCOS-MDW
$205
9/25Wed
2 stopsDelta
9h 18mCOS-MDW
$304
6/27Thu
3 stops
21h 17mCOS-MDW
$355
10/25Fri
2 stopsDelta
8h 55mCOS-MDW
$534
6/4Tue
2 stopsDelta
10h 06mCOS-MDW
$583

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Colorado Springs - Chicago Midway Airport Flights

Departure:

Colorado Springs (COS)United States

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - Colorado Springs

Cabin classes: