COS - CHI

$119 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 9/9. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$267
Typical prices: $368-$316
Delta
Tue 8/25Sat 8/29
COS - MDW • 1 stop
Cheapest non-stop
$271
Typical prices: $502-$378
United Airlines
Wed 7/15Wed 7/29
COS - ORD • Non-stop
Top airlines
Cheapest • from $267 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with American Airlines, Southwest and United Airlines. Average duration is 2h 36m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 3% average savings
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $334 (round-trip)
Shortest trip • 4h 36m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 5 weeks in advance save around 58% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 31% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
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
Delta Logo
11:27 am - 6:01 pm
COS
-
MDW
5h 34m
1 stop
Delta Logo
6:05 am - 12:15 pm
MDW
-
COS
7h 10m
1 stop
$267Delta
Tue, Aug 25 - Sat, Aug 29
Delta Logo
6:00 am - 2:09 pm
COS
-
ORD
7h 09m
1 stop
Delta Logo
5:30 am - 12:15 pm
ORD
-
COS
7h 45m
1 stop
$267Delta
Wed, Jul 15 - Wed, Jul 29
United Airlines Logo
12:11 pm - 3:56 pm
COS
-
ORD
2h 45mnonstop
United Airlines Logo
9:06 am - 11:09 am
ORD
-
COS
3h 03mnonstop
$271United Airlines
Tue, Jul 28 - Tue, Aug 4
American Airlines Logo
12:22 pm - 4:14 pm
COS
-
ORD
2h 52mnonstop
American Airlines Logo
10:00 am - 11:52 am
ORD
-
COS
2h 52mnonstop
$274American Airlines
Tue, Sep 29 - Tue, Oct 6
Southwest Logo
6:15 am - 12:00 pm
COS
-
MDW
4h 45m
1 stop
Southwest Logo
3:40 pm - 5:15 pm
MDW
-
COS
2h 35mnonstop
$277Southwest
Wed, Jul 22 - Tue, Aug 4
American Airlines Logo
5:15 pm - 12:50 am
COS
-
ORD
6h 35m
1 stop
American Airlines Logo
10:00 am - 11:52 am
ORD
-
COS
2h 52mnonstop
$281American Airlines
Tue, Sep 29 - Tue, Oct 6
Southwest Logo
1:15 pm - 4:35 pm
COS
-
MDW
2h 20mnonstop
Southwest Logo
3:40 pm - 5:15 pm
MDW
-
COS
2h 35mnonstop
$283Southwest
Tue, Aug 25 - Sat, Aug 29
American Airlines Logo
12:37 pm - 4:30 pm
COS
-
ORD
2h 53mnonstop
American Airlines Logo
10:56 am - 12:47 pm
ORD
-
COS
2h 51mnonstop
$283American Airlines
Tue, Jul 28 - Tue, Aug 4
American Airlines Logo
3:41 pm - 10:15 pm
COS
-
ORD
5h 34m
1 stop
American Airlines Logo
10:00 am - 11:52 am
ORD
-
COS
2h 52mnonstop
$284American Airlines
Sat, Jul 4 - Tue, Jul 7
United Airlines Logo
5:44 am - 9:45 am
COS
-
ORD
3h 01mnonstop
United Airlines Logo
9:03 am - 11:06 am
ORD
-
COS
3h 03mnonstop
$287United Airlines
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 cheapest return flight from Colorado Springs to Chicago costs $317 on the route between Colorado Springs (COS) and Chicago Midway Airport (MDW). Over the past month, flights between Colorado Springs (COS) and Chicago O'Hare Intl Airport (ORD) were, on average, 3% cheaper than other Colorado Springs-Chicago routes. This 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 Saturdays and avoid leaving on a Monday, as it's usually the priciest day. When flying back from Chicago, Wednesday 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 2 stops layover the cheapest option at $351 on average.

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, which saves you about 58% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 22 weeks before departure.

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$119
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly with an average 24% 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 5 days, the lowest price for a flight from Colorado Springs to Chicago was $119 for a one-way ticket and $267 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 $327 and an overall rating of 7.9, Southwest is the most popular choice. United Airlines is also a great choice for the route, with an average price of $368 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 $226 or less one-way and $391 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.
7.9
SouthwestOverall score based on 4237 reviews
7.0Food
7.5Entertainment
8.1Boarding
8.6Crew
8.0Comfort
Airline reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

2.0 MediocreMatthew, Jun 2026
CVG - MDW
Read more Southwest reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

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.

Over 5 hour delay with minimal updates or ability to standby for alternative flights. During boarding and 1 hr+ wait for takeoff, seats were drenched w water from air conditioning condensation and always leftover crumbs on carpet and seats

Boarded early, left early, arrived 40 mins early! A win win for me!

These airplanes should be illegal. The seats are two tight, it is a safety issue. Wheelchair support was ridiculously slow. We almost missed our flight.

This flight is a quick way to get to Chicago, but a bit expensive.

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

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.

The flight was delayed significantly and we sat on runway after landing for awhile. Best thing was the flight attendant, Jenny, in first class, who was very professional and attentive. She was excellent - the rest of the flight was not.

The flight attendants were extremely sourly and borderline rude. I did not feel appreciated as an AA customer once.

The flight from LA to Chicago was smooth and service was very good overall.

The Mario was so helpful and provided amazing customer service however l have being waiting for a callback for almost a week now and have not heard anything further after l informed them l wanted to change my date of traveling because of my hospital appointment even send them proof and l was unable to use manag your booking on their website is a bit frustrating and l would appreciate an update on My request as soon as possible. And have called them times without numbers no response

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

They lost my baggage and I am still struggling to the information and update

Requested early boarding to disinfect seat, tray table, etc. before general boarding. Instructed to board after wheelchair passengers. Waited on jet bridge behind 12 wheelchair passengers. Stopped immediately after entering plane to wait for gate agent in rear of plane cleaning a seat that was wet, got to my row and found both seats adjacent to mine already occupied, with the lack of room making it impossible for me to clean my own space and defeating the purpose of my boarding early. Cleaned the armrests and tray table as best I could.

The wifi experience is awful. I had to try again and again, taking over 30 minutes, to connect to the wifi. I had to watch the same two ads over and over until I was finally successful. Once connected, it was anything but "high speed" and disconnected at least three times during the flight.

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!

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

Information on your arrival and departure airports