CHI - COS

$109 Find Cheap Flights from Chicago 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 Chicago to Colorado Springs departing on 10/7. 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
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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$241
Typical prices: $398-$313
Southwest
Wed 8/19Sat 8/29
MDW - COS • Non-stop
Cheapest one-way
$109
Southwest
Wed 10/7
MDW - COS • Non-stop
Top airlines
Cheapest • from $241 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Every day
You can fly direct with American Airlines, Southwest and United Airlines. Average duration is 2h 45m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 23% average savings
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $259 (round-trip)
Shortest trip • 4h 33m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 35% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 43% 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
Expert advice
Flight Deals

Cheap Flights from Chicago to Colorado Springs (CHI-COS)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago 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 Chicago to Colorado Springs

Wed, Aug 19 - Sat, Aug 29
Southwest Logo
3:35 pm - 5:00 pm
MDW
-
COS
2h 25mnonstop
Southwest Logo
10:40 am - 2:00 pm
COS
-
MDW
2h 20mnonstop
$241Southwest
Wed, Aug 19 - Sat, Aug 29
United Airlines Logo
8:46 am - 10:33 am
ORD
-
COS
2h 47mnonstop
United Airlines Logo
11:55 am - 3:38 pm
COS
-
ORD
2h 43mnonstop
$247United Airlines
Wed, Aug 19 - Sat, Aug 29
Southwest Logo
3:35 pm - 5:00 pm
MDW
-
COS
2h 25mnonstop
Southwest Logo
2:00 pm - 10:15 pm
COS
-
MDW
7h 15m
1 stop
$250Southwest
Wed, Aug 19 - Sat, Aug 29
Southwest Logo
10:10 am - 4:35 pm
MDW
-
COS
7h 25m
2 stops
Southwest Logo
10:40 am - 2:00 pm
COS
-
MDW
2h 20mnonstop
$256Southwest
Wed, Aug 19 - Sat, Aug 29
United Airlines Logo
5:00 am - 10:44 am
ORD
-
COS
6h 44m
1 stop
United Airlines Logo
11:55 am - 3:38 pm
COS
-
ORD
2h 43mnonstop
$257United Airlines
Sat, Oct 24 - Tue, Oct 27
Southwest Logo
1:55 pm - 5:15 pm
MDW
-
COS
4h 20m
1 stop
Southwest Logo
8:00 am - 3:45 pm
COS
-
MDW
6h 45m
1 stop
$260Southwest
Wed, Aug 19 - Sat, Aug 29
Delta Logo
6:00 am - 10:47 am
ORD
-
COS
5h 47m
1 stop
Delta Logo
6:30 am - 4:51 pm
COS
-
ORD
9h 21m
1 stop
$267Delta
Wed, Oct 21 - Mon, Oct 26
Delta Logo
9:30 am - 9:21 pm
ORD
-
COS
12h 51m
2 stops
Delta Logo
6:00 am - 2:13 pm
COS
-
ORD
7h 13m
1 stop
$272Delta
Wed, Jul 8 - Tue, Jul 14
American Airlines Logo
5:00 am - 9:52 am
ORD
-
COS
5h 52m
1 stop
American Airlines Logo
12:22 pm - 4:14 pm
COS
-
ORD
2h 52mnonstop
$281American Airlines
Thu, Aug 6 - Tue, Aug 11
American Airlines Logo
10:56 am - 12:47 pm
ORD
-
COS
2h 51mnonstop
American Airlines Logo
12:37 pm - 4:30 pm
COS
-
ORD
2h 53mnonstop
$283American Airlines
Booking Insights

KAYAK's insights & trends for Chicago to Colorado Springs flights

Get data-powered insights and trends into flights from Chicago 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 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 to Colorado Springs departing in August.

What is the cheapest Chicago to Colorado Springs flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Chicago to Colorado Springs costs $229 on the route between Chicago O'Hare Intl Airport (ORD) and Colorado Springs (COS). Over the past month, this route was, on average, 23% cheaper than other Chicago-Colorado Springs routes. It is also the most popular route.

What’s the cheapest day of the week to fly from Chicago to Colorado Springs?

The average price of all round-trip flights from Chicago 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 to Colorado Springs. For your return ticket, we recommend flying on a Saturday and avoiding Mondays for the best deals.

What is the cheapest month to fly from Chicago 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 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 to Colorado Springs is December, where tickets cost $105 (return) on average. On the other hand, the most expensive months are July and April, where the average cost of round-trip tickets is $253 and $229 respectively.

Can I save money by flying with a layover from Chicago 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 2 stops layover the cheapest option at $353 on average.

How far in advance should I book a flight from Chicago to Colorado Springs?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Colorado Springs, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago to Colorado Springs, you should book around 3 weeks before departure, which saves you about 35% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 22 weeks before departure.

Expert advice

Expert advice for your flight from Chicago to Colorado Springs

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Good to know

Low seasonFebruary
Cheapest flight$109
Best time to beat the crowds but there is an average 14% increase in price.
Most popular time to fly and prices are also 11% lower on average.
Flight from Chicago Midway Airport to Colorado Springs

When to book flights from Chicago to Colorado Springs

Are your dates flexible? Find out the best times to travel from Chicago 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 flights from Chicago to Colorado Springs

  • What is the cheapest flight from Chicago to Colorado Springs?

    In the last 5 days, the lowest price for a flight from Chicago to Colorado Springs was $119 for a one-way ticket and $241 for a round-trip.

  • Do I need a passport to fly between Chicago and Colorado Springs?

    No

  • Which airports will I be using when flying from Chicago to Colorado Springs?

    Chicago has 2 major airports: Chicago Midway and Chicago O'Hare Intl. Colorado Springs is the only airport in Colorado Springs. You’ll usually find the cheapest deals if you fly from Chicago Midway Airport.

  • Which airlines offer Wi-Fi service onboard planes from Chicago to Colorado Springs?

    American Airlines, and Alaska Airlines offer inflight Wi-Fi service on the Chicago to Colorado Springs flight route.

  • Which aircraft models fly most regularly from Chicago to Colorado Springs?

    The Canadair (Bombardier) Regional Jet 700 is the aircraft model that flies most regularly on the Chicago to Colorado Springs flight route.

  • Which airline alliances offer flights from Chicago to Colorado Springs?

    Star Alliance, and oneworld are the airline alliances operating flights between Chicago and Colorado Springs, with Star Alliance being the most commonly used for this route.

  • On which days can I fly direct from Chicago to Colorado Springs?

    There are nonstop flights from Chicago to Colorado Springs on a daily basis.

  • Which is the best airline for flights from Chicago to Colorado Springs, Southwest or United Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Colorado Springs are Southwest and United Airlines. With an average price for the route of $336 and an overall rating of 7.9, Southwest is the most popular choice. United Airlines is also a great choice for the route, with an average price of $370 and an overall rating of 7.4.

  • How does KAYAK find such low prices on flights from Chicago 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 to Colorado Springs.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago 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 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 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 with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago 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 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 to Colorado Springs

  • Looking for a cheap flight? 25% of our users found flights on this route for $171 or less one-way and $372 or less round-trip.

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

Direct departures

Chicago to Colorado Springs

Monday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Tuesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Wednesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Thursday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Friday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Saturday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Sunday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

See more direct flights

Direct returns

Colorado Springs to Chicago

Monday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Tuesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Wednesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Thursday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Friday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Saturday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Sunday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

See more direct flights

Reviews of the top 3 airlines serving from Chicago 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 Chicago 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.
7.9
SouthwestOverall score based on 4235 reviews
7.5Entertainment
8.6Crew
8.1Boarding
8.0Comfort
7.0Food
Airline reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

2.0 MediocreMatthew, Jun 2026
CVG - MDW
Read more Southwest reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!

Airline is not very senior friendly. Flights are late, forcing us to run to the connecting flight. Food is awful. Wish they would go back to pretzels and peanuts. During flight, pressurization isn’t quite right and all of our ears get plugged. Everything is nickel and dime, charging for boarding, seat selection and legroom. While a screen at the desk in the gate area says check your roll on bag now for free due to space limitation, the employee at the desk will not check the bag without a $100 fee. Insane.

Kayak could’ve posted the correct gate number. Almost missed my flight.

Slow boarding, limited food and drink portions. Bad delays and turbulence

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

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.

Boarded early; and arrived home 40 mins early. After a long flight, it’s nice to be back home early. These flights have no amenities; no snacks. So need to bring your own

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

It was so much better than expected, Ohare is not such a pleasant experience but American Airlines with the new, clean aeroplane and free Wi-Fi was outstanding and the crew so pleasant and helpful.

It wa sort of on time; the cab was left with some trash

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

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

Information on your arrival and departure airports