COS - CHI

$114 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 7/1. 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.
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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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Flights Deals

Cheap Flights from Colorado Springs to Chicago

 
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.

Recent round-trip flight deals from Colorado Springs to Chicago

KAYAK's recommended round-trip deals from the most popular airlines that fly from Colorado Springs to Chicago.
Discover the best prices for you by selecting your travel dates on KAYAK.
United Airlines Logo
6:30 pm - 12:25 amCOS-ORD
4h 55m1 stop
United Airlines Logo
9:15 am - 11:08 amORD-COS
2h 53mnonstop
$237United Airlines
Find Deal
Wed, May 28 - Wed, Jun 4
Southwest Logo
2:40 pm - 6:00 pmCOS-MDW
2h 20mnonstop
Southwest Logo
5:25 pm - 7:00 pmMDW-COS
2h 35mnonstop
$239Southwest
Find Deal
Fri, Jul 4 - Wed, Jul 9
United Airlines Logo
12:04 pm - 3:44 pmCOS-ORD
2h 40mnonstop
United Airlines Logo
9:15 am - 11:08 amORD-COS
2h 53mnonstop
$239United Airlines
Find Deal
Sat, Jun 7 - Tue, Jun 10
United Airlines Logo
6:30 pm - 12:25 amCOS-ORD
4h 55m1 stop
United Airlines Logo
7:10 am - 10:54 amORD-COS
4h 44m1 stop
$247United Airlines
Find Deal
Wed, May 28 - Wed, Jun 4
American Airlines Logo
4:43 pm - 11:56 pmCOS-ORD
6h 13m1 stop
American Airlines Logo
9:42 am - 11:31 amORD-COS
2h 49mnonstop
$249American Airlines
Find Deal
Tue, Jun 3 - Tue, Jun 24
Southwest Logo
2:40 pm - 6:00 pmCOS-MDW
2h 20mnonstop
Southwest Logo
5:55 pm - 11:50 pmMDW-COS
6h 55m1 stop
$249Southwest
Find Deal
Fri, Jul 4 - Wed, Jul 9
American Airlines Logo
6:01 am - 12:25 pmCOS-ORD
5h 24m1 stop
American Airlines Logo
9:42 am - 11:31 amORD-COS
2h 49mnonstop
$250American Airlines
Find Deal
Sat, Jun 7 - Tue, Jun 10
Southwest Logo
7:45 am - 9:30 pmCOS-ORD
12h 45m2 stops
Southwest Logo
5:25 pm - 11:50 pmORD-COS
7h 25m1 stop
$252Southwest
Find Deal
Tue, Jun 3 - Tue, Jun 24
Delta Logo
10:54 am - 5:10 pmCOS-MDW
5h 16m1 stop
Delta Logo
1:05 pm - 9:00 pmMDW-COS
8h 55m1 stop
$259Delta
Find Deal
Sat, Aug 9 - Wed, Aug 20
Delta Logo
6:00 am - 3:06 pmCOS-ORD
8h 06m1 stop
Delta Logo
6:00 am - 10:02 amORD-COS
5h 02m1 stop
$259Delta
Find Deal
Sat, Jun 7 - Tue, Jun 10
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
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.

Southwest

Enjoy two free checked bags up to 50 pounds each, perfect for travelers with extra luggage.


Use EarlyBird Check-In for a better boarding position, avoiding middle seats on busy flights.

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
Useful Info

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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Colorado Springs to Chicago.

Our data shows that the cheapest route for a return flight from Colorado Springs to Chicago cost $255 and was between Colorado Springs (COS) and Chicago O'Hare Intl Airport (ORD). On average, the best prices are found if you fly from Colorado Springs (COS) to Chicago Midway Airport (MDW). The average price for a return flight for this route is $255.

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 Tuesdays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from Chicago, Monday is the cheapest day to fly and Thursday 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 October and November, where the average cost of round-trip tickets is $440 and $413 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 $424, prices are generally cheapest when you fly direct.

How far in advance should I book a flight from Colorado Springs to Chicago?

To calculate weekly average prices, KAYAK takes all prices for each week before departure 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 average of all the values for each week.

To get a below average price on the flight from Colorado Springs to Chicago, you should book around 5 weeks before departure. For the absolute cheapest price, our data suggests you should book 20 weeks before departure.

Good to know

Low seasonFebruary
High seasonJuly
Cheapest flight$114
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly with an average 3% 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 $114 for a one-way ticket and $237 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, United Airlines, Lufthansa, 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 $339 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 $397 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 $149 or less one-way and $348 or less round-trip.

Prefer to fly 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

Southwest, United Airlines, American Airlines

Southwest, United Airlines, +1 more

Tuesday

Southwest, United Airlines, American Airlines

Southwest, United Airlines, +1 more

Wednesday

Southwest, United Airlines, American Airlines

Southwest, United Airlines, +1 more

Thursday

Southwest, United Airlines, American Airlines

Southwest, United Airlines, +1 more

Friday

Southwest, United Airlines, American Airlines

Southwest, United Airlines, +1 more

Saturday

United Airlines, American Airlines, Southwest

United Airlines, American Airlines, +1 more

Sunday

Southwest, United Airlines, American Airlines

Southwest, United Airlines, +1 more

See more direct flights

Direct returns

Chicago to Colorado Springs

Monday

Southwest, United Airlines, American Airlines

Southwest, United Airlines, +1 more

Tuesday

Southwest, United Airlines, American Airlines

Southwest, United Airlines, +1 more

Wednesday

Southwest, United Airlines, American Airlines

Southwest, United Airlines, +1 more

Thursday

Southwest, United Airlines, American Airlines

Southwest, United Airlines, +1 more

Friday

Southwest, United Airlines, American Airlines

Southwest, United Airlines, +1 more

Saturday

United Airlines, American Airlines, Southwest

United Airlines, American Airlines, +1 more

Sunday

Southwest, United Airlines, American Airlines

Southwest, United Airlines, +1 more

See more direct flights
See more direct flights

Top airlines flying 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 4293 reviews
8.0Comfort
8.2Boarding
7.6Entertainment
7.1Food
8.6Crew
Airline reviews

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

4.0 OkayAnonymous, Apr 2025DEN - SEA
Read more Southwest reviews

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.

I really like open seating. I hate that I've heard this is going away. This is one of the unique things that makes Southwest my goto choice.

It seems as though the provisions are even less. Although SWA used to be an economy Airline, that isn't really the case anymore. I paid over $700. for a round trip to Denver and I could have flown just about any airline for the price. The drinks are now in a 6-ounce cup and with ice I'm sure a can would fill more than 2 cups. However, I am very proud of SWA for using paper rather than continuing to contribute to the millions of plastic cups being used each day. I've thought of this fr many years and am so glad to see it come to fruition, if not by only SWA so far.

My original flight was extremely delayed but I was able to join the standby list for an earlier flight. I was grateful for this feature but I wish I could’ve gotten my standby confirmation sooner.

I like that it was on time and the staff was friendly.

No space for our carryon and needed to check at plane before boarding !

Flight was ok. Boarding wasn’t fun. Flights were delayed by 12 minutes on each leg.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.

The crew were very nice. The Chocolate is good and v there’s no entertainment. Thanks

The crew were very nice. I would have appreciated a pillow for comfort. I had a special meal that was sloppy, but the salad was great. Thanks

The plane was in Moline all night. Consequently, we assumed an on time departure at 8:15am. Unfortunately, and as is the normal case with United in Moline, we departed 2.5 hours late. When the crew came, it was discovered that there was very little heat in the plane. Seems this should have been checked hours before the crew arrived. Then when we boarded and the plane was to be de-iced, the United de-icing truck was not working! We awaited the American Airlines truck. All of this caused us to miss our connection in Chicago. My suggestion is never take United Airlines flight from Moline. We have been disappointed 80% of the time and have vowed to not take United again from Moline.

Flight was delayed two hours. No snacks and no tv screens. My bag got stuck in Chicago

The aircrew was solid, the flight was chill, I had no issues. The gate agent was not the best. I was trying to use a military bag upgrade to move my bag from under the seat to the overhead bins and he told me there’s no overhead bins on the plane, argued with me why booking put a military member in basic economy (I don’t really understand this) and made it an issue to even try to help me stating I’d have to call reservations to get a bag upgrade. When every other agent with United can add it at the gate, this man couldn’t be bothered.

They canceled our flight and left us stranded to figure it out

Everything was very good. Was able to change a make run flight leaving on direct earlier in the app -seamless!!! Well done

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

Information on your arrival and departure airports

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