MDW - COS

$151 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 6/2. 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 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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Everything you should know

Cheapest round-trip
$289
Southwest
Wed 10/21Mon 10/26
MDW - COS • Non-stop
Cheapest one-way
$154
Southwest
Tue 6/2
MDW - COS • 1 stop
Top airlines
Cheapest • from $289 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with Southwest. Average duration is 2h 32m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top layover airports
Cheapest • Avg $536 (round-trip)
Shortest trip • 4h 33m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 100% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Colorado Springs!
Flight Deals
Booking Insights
Flight 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

Wed, Oct 21 - Mon, Oct 26
Southwest Logo
3:40 pm - 5:15 pm
MDW
-
COS
2h 35mnonstop
Southwest Logo
2:15 pm - 5:35 pm
COS
-
MDW
2h 20mnonstop
$289Southwest
Wed, Oct 21 - Wed, Oct 21
Southwest Logo
3:40 pm - 5:15 pm
MDW
-
COS
2h 35mnonstop
Southwest Logo
6:55 pm - 5:45 am
COS
-
MDW
9h 50m
1 stop
$303Southwest
Wed, Jun 10 - Tue, Jun 16
Southwest Logo
5:35 pm - 10:55 pm
MDW
-
COS
6h 20m
1 stop
Southwest Logo
6:10 pm - 12:05 am
COS
-
MDW
4h 55m
1 stop
$307Southwest
Tue, Jun 2 - Tue, Jun 9
Southwest Logo
1:55 pm - 9:20 pm
MDW
-
COS
8h 25m
2 stops
Southwest Logo
6:35 am - 2:40 pm
COS
-
MDW
7h 05m
1 stop
$312Southwest
Thu, May 28 - Tue, Jun 2
Southwest Logo
4:35 pm - 12:05 am
MDW
-
COS
8h 30m
2 stops
Southwest Logo
2:30 pm - 9:45 pm
COS
-
MDW
6h 15m
1 stop
$314Southwest
Tue, Jun 30 - Sat, Jul 4
Southwest Logo
5:05 am - 9:55 am
MDW
-
COS
5h 50m
1 stop
Southwest Logo
7:05 am - 10:25 am
COS
-
MDW
2h 20mnonstop
$329Southwest
Wed, Aug 5 - Mon, Aug 10
Southwest Logo
1:55 pm - 8:10 pm
MDW
-
COS
7h 15m
2 stops
Southwest Logo
1:15 pm - 4:35 pm
COS
-
MDW
2h 20mnonstop
$334Southwest
Thu, Aug 6 - Tue, Aug 11
Delta Logo
1:27 pm - 10:56 pm
MDW
-
COS
10h 29m
2 stops
Delta Logo
11:27 am - 6:01 pm
COS
-
MDW
5h 34m
1 stop
$336Delta
Fri, Jun 26 - Tue, Jun 30
Southwest Logo
6:40 pm - 1:20 am
MDW
-
COS
7h 40m
1 stop
Southwest Logo
6:10 pm - 12:05 am
COS
-
MDW
4h 55m
1 stop
$339Southwest
Fri, Jun 5 - Mon, Jun 8
Southwest Logo
4:20 pm - 8:15 pm
MDW
-
COS
4h 55m
1 stop
Southwest Logo
7:55 pm - 5:25 am
COS
-
MDW
8h 30m
1 stop
$341Southwest
Booking Insights

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.

How much is a round-trip flight from Chicago Midway Airport to Colorado Springs?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago Midway Airport to Colorado Springs departing in October.

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 Wednesday, 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 Tuesdays 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 June, where tickets cost $0 (return) on average. On the other hand, the most expensive months are September and March, where the average cost of round-trip tickets is $593 and $537 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.

No, with an average price for the route of $398, prices are generally cheapest when you fly direct.

Good to know

Low seasonApril
Cheapest flight$154
Best time to beat the crowds with an average 44% drop in price.
Most popular time to fly with an average 8% increase in price.
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

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

    There is a maximum of 1 nonstop flight a day that takes off from Chicago Midway Airport and lands in Colorado Springs, with an average flight time of 2h 32m. The most common departure time is 4:00 pm and most flights take off in the afternoon. Each week, there are 7 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 $154 for a one-way ticket and $289 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 Airbus A320-100/200 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 $418 or less round-trip.

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

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago Midway 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

Reviews of the 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 4298 reviews
7.5Entertainment
8.6Crew
8.0Comfort
8.1Boarding
7.0Food
Airline reviews

I'm glad it wasn't only 75% full because I could get a good seat

8.0 ExcellentBobby, May 2026
BNA - GSP
Read more Southwest reviews

I'm glad it wasn't only 75% full because I could get a good seat

if I was good. Not happy that I have to pay extra money to get the seat I need for lake room, but I guess that’s a sign of the times.

Seats were very comfortable. They tilted back. Drinks and snacks were free and served 3 times. Attendants were awesome.

Plane was clean and comfortable. Flight attendants and gate staff were professional, friendly and efficient. Boarding and deplaning were orderly and efficient. All in all, the typical excellent Southwest experience.

Truly terrible. Will never willingly fly southwest again. Seats are worse than before they switched to assigned seating. One flight attendant was the opposite of helpful (rude, unhelpful, dismissive, and as my stranger seatmate said unprompted: a total prick). This caused me, 15 minutes into the flight, to book an alternate return flight home on a competing airline (first class 1.2k purchase instead of my existing planned flight) just so I would not have to ever be on that aircraft, with that terrible service person, with those horrific seats ever again.

Not having a five hour delay with little notice! The crew was very kind, though, and just as tired as we passengers were. The flight didn't depart until nearly 1 am...and no reason was ever given.

We waited in the airplane for over 45 min for a southwest employee to make the flight. This cause over half the plane to miss their connecting flight in Denver. When we confronted the desk upon arrival, they told us the only flight they had was the next day leaving at 8:50 pm!!! Or they offered to get us to Burbank or LA, but after that we were on our own to get back to Santa Barbara. I paid for a flight from sba to bna bna to sba. My re entry into mom mode has been 💯 rough because of southwest mistake with my flight. And now I’m leaving to Reno tomorrow for a vballl tournament and just discovered that my leg in Vegas has me and my 3 kids on a stand by flight even though I had booked these ticket last year November!! Do better southwest!

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

I appreciate the staff who allowed me to board though I arrived a little late! Regarding the assigned seating, I had booked my flight before this change and wasn't aware of the change at the time, and so I didn't select a seat at booking as I didn't realize it was relevant. Better communication about the change would have been helpful for preparing.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

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

Information on your arrival and departure airports