CHI - COS

$64 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 12/10. 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

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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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, Oct 1 - Sat, Oct 4
United Airlines Logo
8:09 pm - 11:52 pmORD-COS
4h 43m1 stop
United Airlines Logo
6:00 am - 9:41 amCOS-ORD
2h 41mnonstop
$156United Airlines
Find Deal
Wed, Oct 1 - Wed, Oct 8
United Airlines Logo
9:10 am - 11:15 amORD-COS
3h 05mnonstop
United Airlines Logo
3:40 pm - 10:39 pmCOS-ORD
5h 59m1 stop
$159United Airlines
Find Deal
Fri, Feb 20 - Mon, Feb 23
United Airlines Logo
9:20 am - 11:18 amORD-COS
2h 58mnonstop
United Airlines Logo
1:00 pm - 4:34 pmCOS-ORD
2h 34mnonstop
$165United Airlines
Find Deal
Wed, Oct 22 - Sat, Oct 25
Southwest Logo
5:30 am - 10:50 amMDW-COS
6h 20m1 stop
Southwest Logo
8:20 am - 11:45 amCOS-MDW
2h 25mnonstop
$167Southwest
Find Deal
Fri, Oct 10 - Sun, Oct 12
United Airlines Logo
5:01 am - 9:05 amORD-COS
5h 04m1 stop
United Airlines Logo
6:00 am - 9:41 amCOS-ORD
2h 41mnonstop
$175United Airlines
Find Deal
Wed, Oct 22 - Sat, Oct 25
Southwest Logo
5:30 am - 10:50 amMDW-COS
6h 20m1 stop
Southwest Logo
6:00 am - 11:40 amCOS-MDW
4h 40m1 stop
$177Southwest
Find Deal
Mon, Nov 3 - Sat, Nov 8
American Airlines Logo
5:18 am - 11:48 amORD-COS
7h 30m1 stop
American Airlines Logo
12:40 pm - 4:26 pmCOS-ORD
2h 46mnonstop
$197American Airlines
Find Deal
Sat, Dec 6 - Wed, Dec 10
American Airlines Logo
10:06 am - 12:08 pmORD-COS
3h 02mnonstop
American Airlines Logo
12:36 pm - 4:21 pmCOS-ORD
2h 45mnonstop
$199American Airlines
Find Deal
Sat, Dec 6 - Wed, Dec 10
Delta Logo
9:59 am - 5:19 pmMDW-COS
8h 20m2 stops
Delta Logo
1:42 pm - 11:32 pmCOS-MDW
8h 50m1 stop
$222Delta
Find Deal
Sat, Dec 6 - Wed, Dec 10
Delta Logo
9:59 am - 10:26 pmMDW-COS
13h 27m2 stops
Delta Logo
8:00 am - 11:32 pmCOS-MDW
14h 32m2 stops
$227Delta
Find Deal

Everything you should know

Our travelers' advice
AI-generated summary based on content written by travel experts
United's Economy Plus offers extra legroom benefits.
Southwest provides two free checked bags per passenger.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
United Airlines
Cheapest • from $156 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
ORD-COS
Cheapest • 16% average savings
ORD-COS
Most popular
Insights
Insights
Insights
Insights
When to book
4 weeks
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 49% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
November
Cheapest • 23% price drop
June
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$156
Overall average: $343
United Airlines
Wed 10/1Sat 10/4
ORD - COS • 1 stop
Cheapest non-stop
$165
Typical prices: $481-581
United Airlines
Fri 2/20Mon 2/23
ORD - COS • Non-stop
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!
Expert advice

Expert advice for your flight from Chicago to Colorado Springs

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
United Airlines

United's Economy Plus offers up to six inches more legroom than standard economy seats.


United's Priority Boarding puts you in Zone 2, avoiding carry-on gate-checking.

Southwest

Southwest offers free carry-on and personal item, but checked bags now incur fees.


Southwest's cancellation policy allows changes up to 10 minutes before departure.

Read more about Southwestby Blane Bachelor
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines

Stefanie Waldek

Stefanie Waldek

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.

Read more
Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor

Blane Bachelor

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.

Read more
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?

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 absolute cheapest return flight from Chicago to Colorado Springs costs $139 on the route between Chicago O'Hare Intl Airport (ORD) and Colorado Springs (COS). However, over the past month, flights between Chicago Midway Airport (MDW) and Colorado Springs (COS) were, on average, 16% cheaper than other Chicago-Colorado Springs routes. The most popular route is between Chicago O'Hare Intl Airport (ORD) and Colorado Springs (COS).

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, Friday is the most expensive day to fly from Chicago to Colorado Springs. For your return ticket, we recommend flying on a Wednesday 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 November, where tickets cost $280 (return) on average. On the other hand, the most expensive months are December and May, where the average cost of round-trip tickets is $469 and $443 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.

No, with an average price for the route of $335, prices are generally cheapest when you fly direct.

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 4 weeks before departure, which saves you about 49% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 18 weeks before departure.

Good to know

Low seasonApril
Cheapest flight$64
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly with an average 8% increase in price.
Flight from Chicago O'Hare 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 3 days, the lowest price for a flight from Chicago to Colorado Springs was $64 for a one-way ticket and $156 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 O'Hare Airport.

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

    Only American Airlines offers inflight Wi-Fi service on the Chicago to Colorado Springs flight route.

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

    The Embraer 175 (Enhanced Winglets) 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?

    oneworld, and Star Alliance 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 $325 and an overall rating of 8.0, Southwest is the most popular choice. United Airlines is also a great choice for the route, with an average price of $391 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 $161 or less one-way and $258 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.
8.0
SouthwestOverall score based on 4248 reviews
8.0Comfort
7.0Food
8.6Crew
8.1Boarding
7.5Entertainment
Airline reviews

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.

6.0 GoodDavid, Aug 2025MCO - DEN
Read more Southwest reviews

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.

The Southwest employees (all two of them) were very nice and cheerful despite the fact the line to self-check a bag (simply drop it off) was hundreds of people long. Thank God I arrived early to the airport because I stood in this line for at least an hour. Once on the flight that had been delayed by an hour, we had no Wi-Fi and thus no entertainment. Finally, I hope the investor strong arm tactics against Southwest pay off in a short-term windfall to your C-Suite because the rest of you are screwed. I have been a faithful Southwest customer for 15 years due to everything you just got rid of. I'm flying to Idaho and Washington in October, both places I used to simply book with Southwest without a second thought now with Frontier (Washington) and United (Idaho) because they offer everything the "new" Southwest does but cheaper and at better times, destinations, etc. This really makes me sad...

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

Flights delayed by 4-6 hours. Boarding was a mess and unclear. Bags were not at arrival airport and had never even been put on the plane. No idea when I’ll get them. Don’t fly into Denver!

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

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

Information on your arrival and departure airports

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