COS - CHI

$88 Find Cheap Flights from Colorado Springs to Chicago

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 Chicago departing on 2/26. 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

 
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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Flight Deals

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

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

Mon, Nov 24 - Thu, Dec 4
American Airlines Logo
12:36 pm - 4:22 pmCOS-ORD
2h 46mnonstop
American Airlines Logo
9:55 am - 12:02 pmORD-COS
3h 07mnonstop
$253American Airlines
Find Deal
Thu, Dec 11 - Sat, Dec 13
American Airlines Logo
12:36 pm - 4:21 pmCOS-ORD
2h 45mnonstop
American Airlines Logo
10:06 am - 12:08 pmORD-COS
3h 02mnonstop
$258American Airlines
Find Deal
Sat, Dec 13 - Tue, Dec 16
United Airlines Logo
12:50 pm - 4:36 pmCOS-ORD
2h 46mnonstop
United Airlines Logo
7:55 pm - 9:57 pmORD-COS
3h 02mnonstop
$261United Airlines
Find Deal
Sat, Dec 6 - Mon, Dec 8
American Airlines Logo
12:38 pm - 4:23 pmCOS-ORD
2h 45mnonstop
American Airlines Logo
9:55 am - 12:02 pmORD-COS
3h 07mnonstop
$264American Airlines
Find Deal
Thu, Dec 11 - Sat, Dec 13
American Airlines Logo
12:36 pm - 4:21 pmCOS-ORD
2h 45mnonstop
American Airlines Logo
8:11 am - 3:45 pmORD-COS
8h 34m1 stop
$268American Airlines
Find Deal
Sat, Dec 13 - Tue, Dec 16
United Airlines Logo
12:50 pm - 4:36 pmCOS-ORD
2h 46mnonstop
United Airlines Logo
2:40 pm - 9:00 pmORD-COS
7h 20m1 stop
$271United Airlines
Find Deal
Thu, Dec 11 - Sat, Dec 13
Southwest Logo
5:15 am - 12:40 pmCOS-MDW
6h 25m1 stop
Southwest Logo
5:15 am - 12:50 pmMDW-COS
8h 35m1 stop
$278Southwest
Find Deal
Thu, Dec 11 - Sat, Dec 13
Delta Logo
1:42 pm - 9:56 pmCOS-ORD
7h 14m1 stop
Delta Logo
5:29 pm - 10:25 pmORD-COS
5h 56m1 stop
$278Delta
Find Deal
Sat, Dec 13 - Tue, Dec 16
Southwest Logo
5:00 am - 1:00 pmCOS-ORD
7h 00m1 stop
Southwest Logo
2:15 pm - 7:40 pmORD-COS
6h 25m1 stop
$281Southwest
Find Deal
Sat, Dec 6 - Mon, Dec 8
Delta Logo
1:42 pm - 10:43 pmCOS-ORD
8h 01m1 stop
Delta Logo
6:45 am - 12:36 pmORD-COS
6h 51m1 stop
$283Delta
Find Deal

Everything you should know

Our travelers' advice
AI-generated summary based on content written by travel experts
United's Economy Plus offers more legroom for comfort.
Southwest allows two free checked bags up to 50 pounds.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
American Airlines
Cheapest • from $253 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
COS-ORD
Cheapest • 6% average savings
COS-ORD
Most popular
Insights
Insights
Insights
Insights
When to travel
February
Cheapest • 10% price drop
October
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$253
Overall average: $401
American Airlines
Mon 11/24Thu 12/4
COS - ORD • Non-stop
Cheapest one-way
$88
Multiple Airlines
Thu 2/26
COS - MDW • 1 stop
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Booking Insights

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

Get data-powered insights and trends into flights from Colorado Springs to Chicago to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Colorado Springs to Chicago flight route?

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

The cheapest return flight from Colorado Springs to Chicago costs $256 on the route between Colorado Springs (COS) and Chicago O'Hare Intl Airport (ORD). Over the past month, this route was, on average, 6% cheaper than other Colorado Springs-Chicago routes. It is also the most popular route.

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

The average price of all round-trip flights from Colorado Springs to Chicago clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Colorado Springs to Chicago, look for departures on Wednesdays and avoid leaving on a Monday, as it's usually the priciest day. When flying back from Chicago, Saturday is the cheapest day to fly and Friday is the most expensive.

What is the cheapest month to fly from Colorado Springs to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Colorado Springs to Chicago, 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 Colorado Springs to Chicago is February, where tickets cost $309 (return) on average. On the other hand, the most expensive months are November and December, where the average cost of round-trip tickets is $414 and $396 respectively.

Can I save money by flying with a layover from Colorado Springs to Chicago?

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 $344, prices are generally cheapest when you fly direct.

Expert advice

Expert advice for your flight from Colorado Springs to Chicago

 
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
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
United Airlines

United's Economy Plus offers up to six inches more legroom, enhancing comfort on domestic flights.


Access free messaging on most United flights, ensuring connectivity without extra costs.

Our travel experts
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
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

Good to know

Low seasonFebruary
Cheapest flight$88
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly and prices are also 4% lower on average.
Flight from Colorado Springs to Chicago Midway Airport

When to book flights from Colorado Springs to Chicago

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

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

    In the last 3 days, the lowest price for a flight from Colorado Springs to Chicago was $88 for a one-way ticket and $253 for a round-trip.

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

    A passport is not required to fly from Colorado Springs to Chicago.

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

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

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

    The Embraer 175 (Enhanced Winglets) is the aircraft model that flies most regularly on the Colorado Springs to Chicago flight route.

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

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

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

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

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

    The two airlines most popular with KAYAK users for flights from Colorado Springs to Chicago are Southwest and United Airlines. With an average price for the route of $323 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 $366 and an overall rating of 7.4.

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

    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.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Colorado Springs to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago 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?

    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 with an airline and back to Colorado Springs with another airline.

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

    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 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

  • Looking for a cheap flight? 25% of our users found flights on this route for $185 or less one-way and $353 or less round-trip.

Prefer to fly direct from Colorado Springs to Chicago?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Colorado Springs to Chicago.
Find which airlines fly direct from Colorado Springs Airport to Chicago, which days they fly and book direct flights.

Direct departures

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

Direct returns

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

Reviews of the top 3 airlines serving from Colorado Springs to Chicago

 
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 Chicago? 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 4241 reviews
8.1Boarding
8.6Crew
7.0Food
8.0Comfort
7.5Entertainment
Airline reviews

Connecting flight is on time and boarding was a breeze!

10.0 ExcellentGabriel, Sep 2025DEN - SMF
Read more Southwest reviews

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.

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

I would have liked to arrive on time - not 5 hours late!

1.5 hour delay, poor service, no compassion from the crew. Terrible experience

Our flight was diverted from being a non-stop to getting within 150 miles and requiring another plane. We heard 4 or 5 different versions from SW as to why we had to stop, then wait for a replacement plane. Five hour delay, weather did not come up as a single excuse.... communication was not clear and well explained. No one really took charge!

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.

Better WiFi. I cannot understand that in 2025, United is so behind on a technology that is now a necessity and still painfully unreliable, slow and keeps disconnecting.

Trip was great. A wild landing in Ottawa with the wind and rain, but the pilot did a great job. Always love flying United.👍

Excellent experience. Starting with the agent at the Premier bag drop who noticed I was very early for my scheduled flight and offered to rebook me on an earlier flight with my seat preference. She would not let me leave the counter until she knew that all of the changes and new boarding pass showed up on my United app. At the gate, the flight boarded quickly such that we departed early and the flight was smooth. We arrived 20 minutes early at ORD and I was able to be home in time for dinner. One of the best flights I've had.

Salina to travers city was great! But the sept 24 Tranverse city was not! Traverse city to chichago was cancelled, i went to Denver & got to Salina 6 hours later!

See previous note about the passenger in Denver who threw my husband's bag out of the overhead bin in order to maker room for his own. And the flight attendant back up the new passenger.

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

This was the best 2 flights I have had with American out of SGF. Great crew both flights.

Excellent - explanations were clear staff was nice and flight was comfortable

Lost bag and 2 days no word leaving for cruise no clothes or stuff

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Food was ok, but not as good as I have had before on AA.

Pretty good. The food was just mediocre, the boarding and crew were good.

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

Information on your arrival and departure airports

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