MDW - COS

$106 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 4/7. 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
Travelers love KAYAK
41 299 237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$211
Overall average: $440
Southwest
Tue 5/12Tue 5/19
MDW - COS • 1 stop
Cheapest non-stop
$310
Southwest
Fri 6/5Sat 6/6
MDW - COS • Non-stop
Top airlines
Southwest
Cheapest • from $211 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top layover airports
Denver (DEN)
Cheapest • Avg $510 (round-trip)
Denver (DEN)
Shortest trip • 5h 20m (one-way)
Insights
Insights
Insights
Insights
When to travel
June
Cheapest • 29% price drop
May
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

Tue, May 12 - Tue, May 19
Southwest Logo
2:10 pm - 8:15 pm
MDW
-
COS
7h 05m
1 stop
Southwest Logo
1:10 pm - 11:20 pm
COS
-
MDW
9h 10m
1 stop
$211Southwest
Tue, May 12 - Tue, May 19
Southwest Logo
7:25 am - 1:50 pm
MDW
-
COS
7h 25m
2 stops
Southwest Logo
2:30 pm - 8:20 pm
COS
-
MDW
4h 50m
1 stop
$216Southwest
Tue, May 5 - Sat, May 9
Southwest Logo
6:10 am - 12:05 pm
MDW
-
COS
6h 55m
1 stop
Southwest Logo
6:20 am - 3:05 pm
COS
-
MDW
7h 45m
1 stop
$229Southwest
Tue, May 5 - Sat, May 9
Southwest Logo
6:10 am - 12:35 pm
MDW
-
COS
7h 25m
1 stop
Southwest Logo
9:50 am - 5:15 pm
COS
-
MDW
6h 25m
2 stops
$234Southwest
Tue, Jun 2 - Sat, Jun 6
Southwest Logo
9:10 am - 4:10 pm
MDW
-
COS
8h 00m
1 stop
Southwest Logo
9:25 am - 12:50 pm
COS
-
MDW
2h 25mnonstop
$237Southwest
Tue, May 5 - Sat, May 9
Southwest Logo
1:55 pm - 8:15 pm
MDW
-
COS
7h 20m
2 stops
Southwest Logo
6:45 am - 5:15 pm
COS
-
MDW
9h 30m
2 stops
$239Southwest
Tue, Jun 2 - Sat, Jun 6
Southwest Logo
1:55 pm - 8:15 pm
MDW
-
COS
7h 20m
2 stops
Southwest Logo
9:25 am - 12:50 pm
COS
-
MDW
2h 25mnonstop
$242Southwest
Sat, Apr 25 - Mon, Apr 27
Southwest Logo
5:30 pm - 8:45 pm
MDW
-
COS
4h 15m
1 stop
Southwest Logo
7:20 pm - 5:00 am
COS
-
MDW
8h 40m
1 stop
$247Southwest
Sat, Apr 25 - Mon, Apr 27
Southwest Logo
5:30 pm - 8:45 pm
MDW
-
COS
4h 15m
1 stop
Southwest Logo
8:00 pm - 5:00 am
COS
-
MDW
8h 00m
2 stops
$252Southwest
Sat, Apr 25 - Mon, Apr 27
Southwest Logo
10:00 am - 4:15 pm
MDW
-
COS
7h 15m
2 stops
Southwest Logo
8:00 pm - 5:00 am
COS
-
MDW
8h 00m
2 stops
$258Southwest
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.

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 June, where tickets cost $293 (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 $532 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 $398 on average.

Find deals

Good to know

Low seasonJanuary
Cheapest flight$106
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly with an average 7% 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

  • 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 $106 for a one-way ticket and $211 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 Canadair (Bombardier) Regional Jet 700 is the aircraft model that flies most regularly on the Chicago Midway Airport to Colorado Springs flight route.

  • 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.

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 4317 reviews
8.0Comfort
7.5Entertainment
8.6Crew
8.1Boarding
7.0Food
Airline reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

4.0 OkayKenny, Mar 2026
TPA - BWI
Read more Southwest reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

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.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

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)