COS - CHI

$136 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 8/19. 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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41 299 237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$279
Typical prices: $373-$372
American Airlines
Tue 8/25Sat 8/29
COS - ORD • Non-stop
Cheapest one-way
$136
Southwest
Wed 8/19
COS - MDW • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
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
Cheapest • from $279 (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 American Airlines, United Airlines and Southwest. Average duration is 2h 52m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 7% average savings
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $310 (round-trip)
Shortest trip • 4h 36m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 28% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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!
Flight Deals
Booking Insights
Expert advice
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

Tue, Aug 25 - Sat, Aug 29
American Airlines Logo
12:07 pm - 3:50 pm
COS
-
ORD
2h 43mnonstop
American Airlines Logo
9:45 am - 11:36 am
ORD
-
COS
2h 51mnonstop
$279American Airlines
Wed, May 20 - Wed, May 27
United Airlines Logo
5:12 pm - 11:56 pm
COS
-
ORD
5h 44m
1 stop
United Airlines Logo
9:06 am - 11:10 am
ORD
-
COS
3h 04mnonstop
$281United Airlines
Tue, Aug 25 - Sat, Aug 29
American Airlines Logo
12:07 pm - 3:50 pm
COS
-
ORD
2h 43mnonstop
American Airlines Logo
1:43 pm - 6:40 pm
ORD
-
COS
5h 57m
1 stop
$289American Airlines
Tue, May 19 - Wed, May 27
American Airlines Logo
1:39 pm - 10:20 pm
COS
-
ORD
7h 41m
1 stop
American Airlines Logo
5:00 am - 9:54 am
ORD
-
COS
5h 54m
1 stop
$291American Airlines
Sat, May 30 - Tue, Jun 2
United Airlines Logo
12:16 pm - 4:02 pm
COS
-
ORD
2h 46mnonstop
United Airlines Logo
9:06 am - 11:10 am
ORD
-
COS
3h 04mnonstop
$295United Airlines
Tue, Aug 25 - Sat, Aug 29
American Airlines Logo
3:51 pm - 11:58 pm
COS
-
ORD
7h 07m
1 stop
American Airlines Logo
3:50 pm - 10:53 pm
ORD
-
COS
8h 03m
1 stop
$299American Airlines
Wed, Jun 3 - Sat, Jun 6
Delta Logo
1:55 pm - 9:53 pm
COS
-
ORD
6h 58m
1 stop
Delta Logo
1:44 pm - 10:22 pm
ORD
-
COS
9h 38m
2 stops
$306Delta
Wed, Jul 1 - Sat, Jul 4
Southwest Logo
6:10 pm - 12:05 am
COS
-
MDW
4h 55m
1 stop
Southwest Logo
4:35 pm - 6:10 pm
MDW
-
COS
2h 35mnonstop
$321Southwest
Tue, Aug 25 - Sat, Aug 29
Delta Logo
10:57 am - 6:05 pm
COS
-
MDW
6h 08m
1 stop
Delta Logo
6:00 am - 12:48 pm
MDW
-
COS
7h 48m
1 stop
$331Delta
Sat, May 30 - Wed, Jun 3
Southwest Logo
4:15 pm - 11:25 pm
COS
-
MDW
6h 10m
1 stop
Southwest Logo
10:15 am - 6:05 pm
MDW
-
COS
8h 50m
1 stop
$341Southwest
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.

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

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

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 absolute cheapest return flight from Colorado Springs to Chicago costs $300 on the route between Colorado Springs (COS) and Chicago O'Hare Intl Airport (ORD). However, over the past month, flights between Colorado Springs (COS) and Chicago Midway Airport (MDW) were, on average, 7% cheaper than other Colorado Springs-Chicago routes. The most popular route is between Colorado Springs (COS) and Chicago O'Hare Intl Airport (ORD).

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 Fridays 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 Sunday 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 October, where tickets cost $149 (return) on average. On the other hand, the most expensive months are November and December, where the average cost of round-trip tickets is $283 and $249 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.

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 $377 on average.

Expert advice

Expert advice for your flight from Colorado Springs to Chicago

 
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 seasonDecember
Cheapest flight$136
Best time to beat the crowds with an average 1% drop in price.
Most popular time to fly with an average 11% increase in price.
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 $136 for a one-way ticket and $279 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 Canadair (Bombardier) Regional Jet 700 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 $304 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 $364 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 $238 or less one-way and $390 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,United Airlines,Southwest

American Airlines,United Airlines, +1 more

Tuesday

American Airlines,United Airlines,Southwest

American Airlines,United Airlines, +1 more

Wednesday

American Airlines,United Airlines,Southwest

American Airlines,United Airlines, +1 more

Thursday

American Airlines,United Airlines,Southwest

American Airlines,United Airlines, +1 more

Friday

American Airlines,United Airlines,Southwest

American Airlines,United Airlines, +1 more

Saturday

American Airlines,United Airlines,Southwest

American Airlines,United Airlines, +1 more

Sunday

American Airlines,United Airlines,Southwest

American Airlines,United Airlines, +1 more

See more direct flights

Direct returns

Chicago to Colorado Springs

Monday

American Airlines,United Airlines,Southwest

American Airlines,United Airlines, +1 more

Tuesday

American Airlines,United Airlines,Southwest

American Airlines,United Airlines, +1 more

Wednesday

American Airlines,United Airlines,Southwest

American Airlines,United Airlines, +1 more

Thursday

American Airlines,United Airlines,Southwest

American Airlines,United Airlines, +1 more

Friday

American Airlines,United Airlines,Southwest

American Airlines,United Airlines, +1 more

Saturday

American Airlines,United Airlines,Southwest

American Airlines,United Airlines, +1 more

Sunday

American Airlines,United Airlines,Southwest

American Airlines,United Airlines, +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 4314 reviews
8.1Boarding
7.5Entertainment
8.6Crew
7.0Food
8.0Comfort
Airline reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

10.0 Excellentlarry, Apr 2026
LGB - PHX
Read more Southwest reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

Great flight. I didn't get a drink because I was asleep whole on the flight.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

WiFi was not working and didn’t have a beverage service

My flight from Denver to Minneapolis was excellent. My flight from Minneapolis to Denver was one of the worst I flights I have ever experienced. I had a window seat, the gentleman in the middle seat was morbidly obese and SW should have made him purchase two seats. His elbow dug into my arm most of the way even after I asked to please be careful. I was literally squashed between the him and the window with no wiggle room. The plane was full so it was not possible to ask for a different seat. I realize I should have complained to the flight attendant but I didn't feel anything could be done to rectify the situation. I fly SW often, I will continue to do so as this was my first negative experience.

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.

The flight was significantly delayed. The inbound flight from EWR was delayed departing because of mechanical problems. My original departure from CLT was 5:28 pm but due to the delay of the inbound flight, after arrival, deplaning, cleaning, boarding, we did not push back from the gate until 9:00 pm. Once in the air, the flight was smooth and what was originally supposed to be an arrival in ORD at 7:30 pm local time turned out to be 9:35 pm.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

newer aircraft, ability to connect my headset via blue tooth for entertainment.

Very comfortable flight, snacks and drinks were good, good communication from crew. Could have used a little more information on timing of boarding for group 5

Great flight. Got to watch a movie. Smooth flight and early arrival at ORD.

It was better than excellent. The staff in Mason City were great. The young woman that pushed my wheelchair did more than could be expected of her. She came from India 17 years ago. I don't remember her name.

After arriving in Chicago, we were taxiing for 1.5 hours with infrequent and untruthful updates about the amount of time it would take to arrive at the gate. Minimally, the team could have provided timing expectations that were more truthful, especially one their original expectations were not met.

It was good, the staff was great, and the food, was as usual, tea and biscuit. Bathroom was clean, and the plane was clean as well.

Very good I can’t complain one bit. Thank you American Airlines for making my flight enjoyable and safe!

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

The new planes (American Eagle) are beautiful and especially comfortable. The flight attendants are consistently professional and courteous. And, while it may seem inconsequential, the new liquid tube of coffee creamer—in contrast to the powdered coffee creamer—makes all the difference in a cup of coffee.

I'm not sure American is capable of on-time arrivals and departures. When you land at ORD, you almost always get held on the tarmac because your gate is still occupied. I may have missed my connection, but that ended up up being significantly delayed as well. Once again, I finally got home well after midnight.

Crew at the gate was very crabby and not at all polite. The plane was very hot the entire flight. And the seat cushion was very worn out.

The staff are very, very professional. It's what flying should feel like.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

Delays with no explanation. It could have been handled better.

Jill was the flight attendant in first class she was fabulous!! Best flight attendant I have had in years.!! And I fly every other week. Other can learn from her!!

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

Information on your arrival and departure airports