COS - MDW

$121 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 5/16. 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

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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Everything you should know

Cheapest round-trip
$239
Typical prices: $300-$409
Multiple Airlines
Thu 4/30Sun 5/3
COS - MDW • 1 stop
Cheapest non-stop
$489
Southwest
Thu 6/4Sun 6/7
COS - MDW • Non-stop
Top airlines
Southwest
Cheapest • from $241 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top layover airports
Dallas (DAL)
Cheapest • Avg $334 (round-trip)
Denver (DEN)
Shortest trip • 4h 36m (one-way)
Insights
Insights
Insights
Insights
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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

Thu, Apr 30 - Sun, May 3
Multiple Airlines Logo
6:46 pm - 2:34 pm
COS
-
MDW
18h 48m
1 stop
Multiple Airlines Logo
6:20 am - 5:56 pm
MDW
-
COS
12h 36m
1 stop
$239Multiple Airlines
Wed, Apr 29 - Sat, May 2
Southwest Logo
6:30 am - 3:25 pm
COS
-
MDW
7h 55m
1 stop
Southwest Logo
5:10 am - 12:35 pm
MDW
-
COS
8h 25m
1 stop
$241Southwest
Wed, Apr 29 - Sat, May 2
Southwest Logo
6:50 pm - 5:25 am
COS
-
MDW
9h 35m
1 stop
Southwest Logo
10:05 am - 6:30 pm
MDW
-
COS
9h 25m
2 stops
$246Southwest
Wed, Apr 29 - Sat, May 2
Southwest Logo
6:30 am - 2:55 pm
COS
-
MDW
7h 25m
2 stops
Southwest Logo
10:30 am - 8:50 pm
MDW
-
COS
11h 20m
2 stops
$251Southwest
Sat, May 9 - Sat, May 16
Southwest Logo
9:50 am - 8:05 pm
COS
-
MDW
9h 15m
2 stops
Southwest Logo
1:55 pm - 8:45 pm
MDW
-
COS
7h 50m
1 stop
$252Southwest
Thu, Apr 30 - Sun, May 3
Southwest Logo
4:05 pm - 11:55 pm
COS
-
MDW
6h 50m
1 stop
Southwest Logo
6:55 am - 11:00 am
MDW
-
COS
5h 05m
1 stop
$260Southwest
Sat, May 9 - Sat, May 16
Delta Logo
1:55 pm - 9:09 pm
COS
-
MDW
6h 14m
1 stop
Delta Logo
6:23 am - 12:48 pm
MDW
-
COS
7h 25m
1 stop
$261Delta
Thu, May 14 - Mon, May 18
Delta Logo
1:55 pm - 9:09 pm
COS
-
MDW
6h 14m
1 stop
Delta Logo
9:22 am - 9:27 pm
MDW
-
COS
13h 05m
2 stops
$266Delta
Sat, May 9 - Sat, May 16
Delta Logo
8:15 am - 6:33 pm
COS
-
MDW
9h 18m
2 stops
Delta Logo
1:22 pm - 10:22 pm
MDW
-
COS
10h 00m
2 stops
$271Delta
Thu, Apr 9 - Tue, Apr 14
Southwest Logo
5:00 am - 11:50 am
COS
-
MDW
5h 50m
1 stop
Southwest Logo
2:55 pm - 8:45 pm
MDW
-
COS
6h 50m
1 stop
$276Southwest
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 Wednesdays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from Chicago Midway Airport, Wednesday is the cheapest day to fly and Sunday is the most expensive.

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 $385, prices are generally cheapest when you fly direct.

Find deals

Good to know

Low seasonSeptember
Cheapest flight$121
Best time to beat the crowds with an average 25% drop in price.
Most popular time to fly and prices are also 17% 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 $121 for a one-way ticket and $239 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 Airbus A319 is the aircraft model that flies most regularly on the Colorado Springs to Chicago Midway Airport flight route.

  • 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 $460 or less round-trip.

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 4320 reviews
8.0Comfort
7.5Entertainment
8.1Boarding
7.0Food
8.6Crew
Airline reviews

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

8.0 ExcellentNick, Mar 2026
BOS - MDW
Read more Southwest reviews

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

My flight from Denver to Minneapolis was excellent. My flight from Minneapolis to Denver was one of the worst I flights I have ever experienced. I had a window seat, the gentleman in the middle seat was morbidly obese and SW should have made him purchase two seats. His elbow dug into my arm most of the way even after I asked to please be careful. I was literally squashed between the him and the window with no wiggle room. The plane was full so it was not possible to ask for a different seat. I realize I should have complained to the flight attendant but I didn't feel anything could be done to rectify the situation. I fly SW often, I will continue to do so as this was my first negative experience.

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

Everything went smoothly and we even arrived a little bit early.

The seats were comfortable, and the boarding process was pretty smooth.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Connecting flight is on time and boarding was a breeze!

Excellent. Would encourage Southwest to keep current boarding procedures with free style seating. Makes for a fantastic experience

WiFi did not work. For as outrageous as these flights cost, when they’re advertised with certain services/ features they should be in working order

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

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)