COS - CHI

$111 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 5/16. 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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Everything you should know

Cheapest round-trip
$221
Overall average: $348
American Airlines
Sat 5/2Sat 5/9
COS - ORD • Non-stop
Cheapest one-way
$111
Typical prices: $221-$252
American Airlines
Sat 5/16
COS - ORD • 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 $221 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
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Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with American Airlines and United Airlines. Average duration is 2h 47m
Direct flights
Direct flights
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Direct flights
Direct flights
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Top routes
Cheapest • 29% 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 • 15% price drop
Most popular
Good to know
Good to know
+1
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Good to know
Good to know
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We hope you love your trip to Chicago!
Flight Deals
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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

Sat, May 2 - Sat, May 9
American Airlines Logo
12:22 pm - 4:09 pm
COS
-
ORD
2h 47mnonstop
American Airlines Logo
9:53 am - 11:52 am
ORD
-
COS
2h 59mnonstop
$221American Airlines
Thu, Apr 30 - Sun, May 3
Multiple Airlines Logo
6:46 pm - 5:00 pm
COS
-
ORD
21h 14m
1 stop
Multiple Airlines Logo
7:45 am - 5:56 pm
ORD
-
COS
11h 11m
1 stop
$230Multiple Airlines
Wed, Apr 29 - Wed, May 6
Southwest Logo
2:30 pm - 8:20 pm
COS
-
MDW
4h 50m
1 stop
Southwest Logo
6:30 am - 9:45 am
MDW
-
COS
4h 15m
1 stop
$241Southwest
Wed, Apr 29 - Wed, May 6
Southwest Logo
9:10 am - 6:50 pm
COS
-
ORD
8h 40m
1 stop
Southwest Logo
7:45 am - 4:10 pm
ORD
-
COS
9h 25m
1 stop
$241Southwest
Wed, Apr 29 - Wed, May 6
American Airlines Logo
12:22 pm - 4:09 pm
COS
-
ORD
2h 47mnonstop
American Airlines Logo
9:53 am - 11:52 am
ORD
-
COS
2h 59mnonstop
$242American Airlines
Wed, Apr 29 - Wed, May 6
American Airlines Logo
12:22 pm - 4:09 pm
COS
-
ORD
2h 47mnonstop
American Airlines Logo
9:53 am - 11:52 am
ORD
-
COS
2h 59mnonstop
$243American Airlines
Wed, Apr 29 - Wed, May 6
Southwest Logo
6:30 am - 2:55 pm
COS
-
MDW
7h 25m
2 stops
Southwest Logo
2:10 pm - 8:15 pm
MDW
-
COS
7h 05m
1 stop
$246Southwest
Wed, Apr 29 - Wed, May 6
Southwest Logo
12:40 pm - 11:55 pm
COS
-
ORD
10h 15m
2 stops
Southwest Logo
6:15 am - 12:35 pm
ORD
-
COS
7h 20m
1 stop
$246Southwest
Wed, Apr 29 - Wed, May 6
Southwest Logo
6:30 am - 2:55 pm
COS
-
MDW
7h 25m
2 stops
Southwest Logo
1:55 pm - 9:20 pm
MDW
-
COS
8h 25m
2 stops
$251Southwest
Thu, May 14 - Mon, May 18
Delta Logo
1:55 pm - 9:09 pm
COS
-
MDW
6h 14m
1 stop
Delta Logo
9:22 am - 9:27 pm
MDW
-
COS
13h 05m
2 stops
$266Delta
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 May.

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 $247 on the route between Colorado Springs (COS) and Chicago O'Hare Intl Airport (ORD). Over the past month, this route was, on average, 29% 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 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 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 January, where tickets cost $286 (return) on average. On the other hand, the most expensive months are November and June, where the average cost of round-trip tickets is $413 and $365 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 $346, prices are generally cheapest when you fly direct.

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$111
Best time to beat the crowds but there is an average 5% increase in price.
Most popular time to fly with an average 8% increase in price.
Flight from Colorado Springs to Chicago O'Hare 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 $111 for a one-way ticket and $221 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 $328 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 $354 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 $189 or less one-way and $410 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

American Airlines,United Airlines

Tuesday

American Airlines,United Airlines

American Airlines,United Airlines

Wednesday

American Airlines,United Airlines

American Airlines,United Airlines

Thursday

American Airlines,United Airlines

American Airlines,United Airlines

Friday

American Airlines,United Airlines

American Airlines,United Airlines

Saturday

American Airlines,United Airlines

American Airlines,United Airlines

Sunday

American Airlines,United Airlines

American Airlines,United Airlines

See more direct flights

Direct returns

Chicago to Colorado Springs

Monday

American Airlines,United Airlines

American Airlines,United Airlines

Tuesday

American Airlines,United Airlines

American Airlines,United Airlines

Wednesday

American Airlines,United Airlines

American Airlines,United Airlines

Thursday

American Airlines,United Airlines

American Airlines,United Airlines

Friday

American Airlines,United Airlines

American Airlines,United Airlines

Saturday

American Airlines,United Airlines

American Airlines,United Airlines

Sunday

American Airlines,United Airlines

American Airlines,United Airlines

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 4318 reviews
8.1Boarding
8.0Comfort
7.0Food
8.6Crew
7.5Entertainment
Airline reviews

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

8.0 ExcellentNick, Mar 2026
BOS - MDW
Read more Southwest reviews

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

Everything went smoothly and we even arrived a little bit early.

The seats were comfortable, and the boarding process was pretty smooth.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

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.

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

Both of my flights arrived early and check in process was smooth

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

They did the one thing that really matters - got to Chicago early.

There was no inflight service. Once we landed we were delayed to find a gate for an hour and a half which was 1/2 the total time in the air.

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

It was good experience this time. The flight was on time.

There was a delay with the plan which cause the flight to leave later and once arrived in Chicago there was another delay and some passengers missed their connecting flights

The gate agent had a really bad attitude and refused to help me get on the standby list. She just handed me a card and said I needed to call a number. I asked her to help with the AA app on my phone and she just shrugged and said she didnt know. After a few phone calls, I eventually just went to a different gate agent on the other side of the terminal and got the help I needed.

Overall, my last three trips on American Airlines have all been either delayed or "rescheduled" due to mechanical issues. At least on delay caused me to miss two possible connecting flights each later than the first. My last option for my last connection required the assistance of the onsite service desk (O'Hare Airport). The wait time for the service desk was such that it jeopardized getting booked on the last connecting flight available for the night. Suffice it to say, my latest experiences with American Airlines have caused me extensive loss of productive business and personal time and can therefore be classified as significantly less than satisfactory.

Waiting for gate in RDU for more than 20mins is crazy.

American Airlines was great and worked very hard to change my ticket so I could get an earlier, direct flight back to Dallas. However, I was informed that Kayak made mistakes with my itinerary and classified my ticket as desiring to be on the earlier flight instead of taking the necessary step of calling AA to get me on the standby list. This ended up keeping me from being added to the standby list and delayed me getting home by 6 hours. I am happy to discuss this further with Kayak so they can correct their procedures so this won't happen again.

Waited for oxygen tanks for 30 minutes after boarding was complete.

We flew in first class. The crew did not offer drinks before the flight took off, but they treated us well during the flight. The food was excellent. There was actually too much food served, but it was nice to have all the options.

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

Information on your arrival and departure airports