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COS - MDW

Find cheap flights from Colorado Springs to Chicago Midway Airport from $240

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Colorado Springs to Midway departing on 4/27. 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 4/27
Sat 5/4

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 46,342,885 times on KAYAK, and here is why:

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Cheap flight deals from Colorado Springs to Midway

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
6:50 am - 2:53 pmCOS-MDW
7h 03m1 stop
12:45 pm - 8:44 pmMDW-COS
8h 59m1 stop
$240Delta
Find Deal
Sat, Apr 27 - Tue, Apr 30
8:20 am - 10:14 pmCOS-MDW
12h 54m2 stops
12:45 pm - 8:44 pmMDW-COS
8h 59m1 stop
$275Delta
Find Deal
Tue, Apr 16 - Tue, Apr 30
8:20 am - 10:14 pmCOS-MDW
12h 54m2 stops
1:25 pm - 8:44 pmMDW-COS
8h 19m2 stops
$337Delta
Find Deal
Tue, Apr 16 - Tue, Apr 30
6:50 am - 2:53 pmCOS-MDW
7h 03m1 stop
10:00 am - 7:32 pmMDW-COS
10h 32m2 stops
$349Delta
Find Deal
Sun, Apr 14 - Wed, Apr 17
6:50 am - 2:53 pmCOS-MDW
7h 03m1 stop
12:45 pm - 8:44 pmMDW-COS
8h 59m1 stop
$428Delta
Find Deal
Sun, Apr 14 - Wed, Apr 17
6:50 am - 2:53 pmCOS-MDW
7h 03m1 stop
10:00 am - 7:32 pmMDW-COS
10h 32m2 stops
$475Delta
Find Deal
Mon, Apr 15 - Wed, Apr 17
6:00 am - 2:55 pmCOS-MDW
7h 55m1 stop
12:42 pm - 8:37 pmMDW-COS
8h 55m1 stop
$486Delta
Find Deal
Fri, May 10 - Sun, May 12
6:50 am - 4:10 pmCOS-MDW
8h 20m1 stop
12:45 pm - 8:44 pmMDW-COS
8h 59m1 stop
$538Delta
Find Deal
Tue, Apr 16 - Tue, Apr 30
6:50 am - 2:53 pmCOS-MDW
7h 03m1 stop
12:45 pm - 8:44 pmMDW-COS
8h 59m1 stop
$548Delta
Find Deal
Mon, Apr 15 - Wed, Apr 17
6:00 am - 2:55 pmCOS-MDW
7h 55m1 stop
9:32 am - 8:37 pmMDW-COS
12h 05m2 stops
$553Delta
Find Deal
Fri, May 10 - Sun, May 12

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 18m. The most common departure time is 7:00 am and most flights take off in the morning. Each week, there are 11 flights. The most frequent day of departure is Friday, when 18% of all weekly flights depart. The fewest flights depart on a Saturday.

How long does a flight from Colorado Springs to Chicago Midway Airport take?

The average nonstop flight takes 7h 03m, covering a distance of 915 miles.

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

Early birds can take the earliest flight from Colorado Springs at 7:20 am and will be landing in Chicago Midway Airport at 10:40 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 4:20 pm and lands at 7:45 pm.

Good to know

Low season

September

High season

July

Cheapest flight

$240
Best time to beat the crowds with an average 45% drop in price.
Most popular time to fly and prices are also 18% 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 3 days, the lowest price for a flight from Colorado Springs to Chicago Midway Airport was $388 for a one-way ticket and $240 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

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 KAYAK reviews.
8.0
DeltaOverall score based on 11402 reviews
81overall
79comfort
75food
80entertainment
86crew
82boarding
Airline reviews

Carly the flight attendant was extremely helpful and very accommodating to passengers on the flight from what I noticed. Couldn't be more satisfied with the service and assistance from Delta's flight attendant, Thanks again Carly!!

Read more about Delta

Carly the flight attendant was extremely helpful and very accommodating to passengers on the flight from what I noticed. Couldn't be more satisfied with the service and assistance from Delta's flight attendant, Thanks again Carly!!

I didn’t not like that I could not select my seat and ended up with the worse seat.

I didn’t like that I could not select my seat and was assigned a seat when I checked in at LAX

Delta did an awful job w logistics at DTW. Missed connection. We were there an hour early. SUCKED

Inflight entertainment stopped working as we taxi to runway and never worked again until landing and taxi to gate. Grrrr

Had to run to make it only to have the flight delayed to wait for all the late connectors Second drink service skipped up

Boarding was a sh!t show. JFK BOARDING was awful. The agent called three sections at a time Clogging the area then yelling at people to not block the walk way. How are you going to call delta one , premium select and comfort plus at once and the yell at highest paying passengers. Need to do a lot better and the flight attendants in the galley need to understand that their voices travel. They were talking about others and everyone in the cabin heard them

Uncomfortable seats on 14 hour flight. Mediocre food. On time and great crew.

MSP to Atlanta was much better than Atlanta to St. Kitts. Paid $180 each for myself and wife for Delta comfort from Atlanta to St. Kitts. Seats were more narrow and obviously old and worn out. Tailbone is killing me. Seat would not recline. Seats behind reclined and we were not an exit row or in front of an exit row. Entertainment did not work in that the movie jumped forward and back and there was no audio. The plug in the arm rest was loose. Flight attendant tried “resetting” the video for my seat but no good. She never checked back. Someone else near me had the same issue. Touch screen was unresponsive. No where near as comfortable as MSP to Atlanta flight. 3 plus hrs. flight time without the basic amenities and not even remotely close to comfortable but paid for Comfort plus. I will be very disappointed if I have the same on my return “Comfort Plus” flight St. Kitts to Atlanta. At the very least my wife and I should be refunded for round trip “Comfort Plus” charges. Please feel free to contact me directly for more details.

public website still broken for years randomly blocking browsers with privacy options active after loading a page maybe once. check-in on laptop was almost impossible but eventually randomly worked. had to print pass at airport since couldn't get back in to load digital pass on mobile firefox or chrome. red eye flight so smooth onboarding, plenty of room to spread out, easy offboarding. onboard wifi instructions mention vpn can cause problems connecting but fails to also mention private dns. no printed or built in menu list, seems weird to require personal device to point at qr code link for menu which does not even allow direct ordering. people with health condition risk related dietary restrictions trying to avoid for example cholesterol and sugar are left guessing what they can order either way without nutritional info highlights (cranberry juice was minute maid cocktail with as much suger as typical can of soda). tap to pay wasn't working and always seems sketchy to manually enter card info. good movie variety, so limited tv was okay.

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.
4/3Wed
2 stopsDelta
9h 11mCOS-MDW
$388
4/11Thu
1 stopDelta
7h 03mCOS-MDW
$451
4/6Sat
2 stopsDelta
9h 11mCOS-MDW
$654

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Last minute flights from Colorado Springs to Midway

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Colorado Springs to Chicago that are departing in the next 10 days.
3/29Fri
multi-stopDelta
10h 03mCOS-MDW
4/1Mon
multi-stopDelta
9h 08mMDW-COS
$867
3/31Sun
multi-stopDelta
10h 03mCOS-MDW
4/2Tue
multi-stopDelta
8h 20mMDW-COS
$872
3/29Fri
multi-stopDelta
10h 03mCOS-MDW
4/1Mon
multi-stopDelta
10h 25mMDW-COS
$1,305
4/1Mon
multi-stopDelta
9h 11mCOS-MDW
4/2Tue
multi-stopDelta
8h 20mMDW-COS
$1,443
4/1Mon
multi-stopDelta
10h 03mCOS-MDW
4/2Tue
multi-stopDelta
13h 51mMDW-COS
$1,511

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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: