COS - CHI

$98 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 2/24. 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
$205
Typical prices: $254-$349
United Airlines
Sat 2/14Tue 2/17
COS - ORD • 1 stop
Cheapest non-stop
$230
Typical prices: $370-$545
American Airlines
Thu 4/9Tue 4/14
COS - ORD • Non-stop
Our travelers' advice
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
United Airlines
Cheapest • from $205 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
COS
-
ORD
Cheapest • 36% average savings
COS
-
ORD
Most popular
Insights
Insights
Insights
Insights
When to travel
February
Cheapest • 15% price drop
June
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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

Sat, Feb 14 - Tue, Feb 17
United Airlines Logo
1:40 pm - 9:29 pm
COS
-
ORD
6h 49m
1 stop
United Airlines Logo
8:45 am - 10:55 am
ORD
-
COS
3h 10mnonstop
$205United Airlines
Thu, Apr 30 - Tue, May 12
American Airlines Logo
12:21 pm - 4:06 pm
COS
-
ORD
2h 45mnonstop
American Airlines Logo
9:50 am - 11:51 am
ORD
-
COS
3h 01mnonstop
$212American Airlines
Sat, Feb 14 - Tue, Feb 17
United Airlines Logo
1:40 pm - 7:50 pm
COS
-
ORD
5h 10m
1 stop
United Airlines Logo
7:10 am - 10:52 am
ORD
-
COS
4h 42m
1 stop
$215United Airlines
Thu, Mar 5 - Mon, Mar 9
Delta Logo
12:00 pm - 9:52 pm
COS
-
ORD
8h 52m
1 stop
Delta Logo
9:50 am - 8:28 pm
ORD
-
COS
11h 38m
2 stops
$220Delta
Thu, Feb 26 - Sat, Feb 28
American Airlines Logo
12:30 pm - 4:10 pm
COS
-
ORD
2h 40mnonstop
American Airlines Logo
7:20 am - 12:48 pm
ORD
-
COS
6h 28m
1 stop
$223American Airlines
Thu, Feb 19 - Sat, Feb 21
United Airlines Logo
5:05 pm - 10:52 pm
COS
-
ORD
4h 47m
1 stop
United Airlines Logo
8:45 am - 10:55 am
ORD
-
COS
3h 10mnonstop
$225United Airlines
Fri, Jun 12 - Tue, Jun 16
United Airlines Logo
12:16 pm - 4:02 pm
COS
-
ORD
2h 46mnonstop
United Airlines Logo
9:20 am - 11:24 am
ORD
-
COS
3h 04mnonstop
$229United Airlines
Thu, Apr 30 - Tue, May 12
Southwest Logo
7:20 pm - 5:00 am
COS
-
MDW
8h 40m
1 stop
Southwest Logo
2:55 pm - 8:45 pm
MDW
-
COS
6h 50m
1 stop
$232Southwest
Fri, Feb 20 - Mon, Feb 23
Delta Logo
12:00 pm - 9:52 pm
COS
-
ORD
8h 52m
1 stop
Delta Logo
6:45 am - 12:25 pm
ORD
-
COS
6h 40m
1 stop
$232Delta
Thu, Apr 30 - Tue, May 12
Southwest Logo
7:20 pm - 5:00 am
COS
-
MDW
8h 40m
1 stop
Southwest Logo
1:55 pm - 8:15 pm
MDW
-
COS
7h 20m
2 stops
$237Southwest
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 February.

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 $229 on the route between Colorado Springs (COS) and Chicago O'Hare Intl Airport (ORD). Over the past month, this route was, on average, 36% 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 $279 (return) on average. On the other hand, the most expensive months are November and April, where the average cost of round-trip tickets is $413 and $358 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 $318, 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$98
Best time to beat the crowds but there is an average 7% 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 $98 for a one-way ticket and $205 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 $317 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 $353 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 $158 or less one-way and $321 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 4268 reviews
7.0Food
8.1Boarding
8.6Crew
8.0Comfort
7.5Entertainment
Airline reviews

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

10.0 ExcellentAnonymous, Jan 2026
PHX - MDW
Read more Southwest reviews

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.

Great vacation. Can't wait till next year for another one.

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.

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.

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.

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

Very bad! They kept delaying my flight and wouldn’t do anything about it

Door to door, the crew and staff were amazing. It was a stressful travel day with delays, but they were focused on customers and doing what they could to get us to our destinations.

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

Little warm on the plane and delayed for an hour

So excited very proud first of all I wanna thank kayak all updates very professional and fast alart And amazing cabin crew so nice to me they deserve big salute

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

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.

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

Information on your arrival and departure airports