CLO - ORD

$224 Find Cheap Flights from Cali 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 Cali to Chicago departing on 5/27. 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 O'Hare Intl Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Cali 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 Cali 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
$379
Overall average: $437
Spirit Airlines
Tue 4/7Tue 4/14
CLO - ORD • 2 stops
Cheapest one-way
$224
Typical prices: $248-$343
Spirit Airlines
Wed 5/27
CLO - ORD • 1 stop
Top airlines
Spirit Airlines
Cheapest • from $379 (round-trip)
Copa Airlines
Best reviews • 7.5 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Cali and Chicago. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Fort Lauderdale (FLL)
Cheapest • Avg $349 (round-trip)
Panama City (PTY)
Shortest trip • 9h 08m (one-way)
Insights
Insights
Insights
Insights
When to book
7 weeks
in advance
Our data shows that travelers who book at least 7 weeks in advance save around 23% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
September
Cheapest • 17% price drop
August
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
Flight Deals

Cheap Flights from Cali to Chicago (CLO-ORD)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Cali 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 Cali to Chicago

Tue, Apr 7 - Tue, Apr 14
Spirit Airlines Logo
2:24 pm - 11:50 am
CLO
-
ORD
21h 26m
2 stops
Spirit Airlines Logo
6:10 pm - 1:19 pm
ORD
-
CLO
19h 09m
1 stop
$379Spirit Airlines
Tue, Apr 7 - Tue, Apr 14
Spirit Airlines Logo
2:24 pm - 11:17 am
CLO
-
ORD
20h 53m
1 stop
Spirit Airlines Logo
6:10 pm - 1:19 pm
ORD
-
CLO
19h 09m
1 stop
$401Spirit Airlines
Mon, Jun 1 - Fri, Jun 12
Multiple Airlines Logo
2:24 pm - 12:14 am
CLO
-
ORD
9h 50m
1 stop
Multiple Airlines Logo
11:20 pm - 3:35 pm
ORD
-
CLO
16h 15m
1 stop
$417Multiple Airlines
Mon, Mar 9 - Fri, Mar 13
Avianca Logo
6:45 pm - 9:20 pm
CLO
-
ORD
26h 35m
1 stop
Avianca Logo
8:50 am - 10:35 pm
ORD
-
CLO
13h 45m
2 stops
$426Avianca
Wed, Apr 22 - Wed, Apr 29
LATAM Airlines Logo
5:25 am - 8:16 pm
CLO
-
ORD
14h 51m
2 stops
LATAM Airlines Logo
5:15 am - 6:05 pm
ORD
-
CLO
12h 50m
2 stops
$434LATAM Airlines
Wed, Apr 22 - Wed, Apr 29
LATAM Airlines Logo
10:50 pm - 8:16 pm
CLO
-
ORD
21h 26m
2 stops
LATAM Airlines Logo
5:15 am - 6:05 pm
ORD
-
CLO
12h 50m
2 stops
$435LATAM Airlines
Sat, Apr 18 - Sun, Apr 26
Copa Airlines Logo
12:06 pm - 1:13 am
CLO
-
ORD
13h 07m
1 stop
Copa Airlines Logo
8:06 am - 5:36 pm
ORD
-
CLO
9h 30m
1 stop
$437Copa Airlines
Mon, May 4 - Mon, May 25
Avianca Logo
9:45 am - 9:20 pm
CLO
-
ORD
11h 35m
1 stop
Avianca Logo
11:20 pm - 12:00 pm
ORD
-
CLO
12h 40m
1 stop
$439Avianca
Mon, May 4 - Mon, May 25
Avianca Logo
8:25 am - 9:20 pm
CLO
-
ORD
12h 55m
1 stop
Avianca Logo
11:20 pm - 9:00 am
ORD
-
CLO
9h 40m
1 stop
$440Avianca
Sat, Apr 18 - Sun, Apr 26
American Airlines Logo
2:15 pm - 7:31 am
CLO
-
ORD
17h 16m
2 stops
American Airlines Logo
8:46 pm - 1:08 pm
ORD
-
CLO
16h 22m
2 stops
$446American Airlines
Booking Insights

KAYAK's insights & trends for Cali to Chicago flights

Get data-powered insights and trends into flights from Cali to Chicago to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Cali to Chicago O'Hare Intl Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Cali to Chicago O'Hare Intl Airport, 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 Cali to Chicago O'Hare Intl Airport is September, where tickets cost $395 (return) on average. On the other hand, the most expensive months are May and December, where the average cost of round-trip tickets is $570 and $552 respectively.

How far in advance should I book a flight from Cali to Chicago O'Hare Intl Airport?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Cali to Chicago O'Hare Intl Airport, 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 Cali to Chicago O'Hare Intl Airport, you should book around 7 weeks before departure, which saves you about 23% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 19 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$224
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly and prices are also 11% lower on average.
Flight from Cali to Chicago

When to book flights from Cali to Chicago

Are your dates flexible? Find out the best times to travel from Cali 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 Cali to Chicago flights

  • What is the cheapest flight from Cali to Chicago O'Hare Intl Airport?

    In the last 3 days, the lowest price for a flight from Cali to Chicago O'Hare Intl Airport was $224 for a one-way ticket and $379 for a round-trip.

  • Do I need a passport to fly between Cali and Chicago?

    Yes

  • Which airports will I be using when flying from Cali to Chicago?

    Cali airport is called Cali Alfonso B. Aragon Intl and the only airport in Chicago is Chicago O'Hare Intl.

  • Which aircraft models fly most regularly from Cali to Chicago?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Cali to Chicago?

    oneworld, and Star Alliance are the airline alliances operating flights between Cali and Chicago, with oneworld being the most commonly used for this route.

  • Which is the best airline for flights from Cali to Chicago, Copa Airlines or American Airlines?

    The two airlines most popular with KAYAK users for flights from Cali to Chicago are Copa Airlines and American Airlines. With an average price for the route of $507 and an overall rating of 7.5, Copa Airlines is the most popular choice. American Airlines is also a great choice for the route, with an average price of $478 and an overall rating of 7.2.

  • How does KAYAK find such low prices on flights from Cali 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 Cali to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Cali to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Cali 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 Cali 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 Cali with another airline. Booking your flights between Cali and ORD can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Cali 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 Cali up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 3 airlines serving from Cali to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Cali 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 Cali 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.
7.5
Copa AirlinesOverall score based on 1555 reviews
8.1Crew
7.4Comfort
7.8Boarding
6.8Food
6.8Entertainment
Airline reviews

A lot things happened in this trip.The fly should be less stress.

6.0 GoodIrma, Jan 2026
PTY - MIA
Read more Copa Airlines reviews

A lot things happened in this trip.The fly should be less stress.

The flight was good overall. Everything went smoothly, although the landing was a bit rough. Still, it was a pleasant experience

Very strict carry on rules meant most of the plane had to gate check their luggage. As is often the case had things that were broken because of this, but I appreciated not being charged to gate check. Otherwise good flight and great crew once on the plane

Some of the Air hostesses are not that friendly. Need improvement

Simply as follows:- First, there was no vegetarian option for the meal Second, only 2 washrooms for the entire economy class.

Boarding was quick & efficient; they gave boarding groups due priority; staff & air crew were very cordial and helpful, pleasant flight.

Cops Airlines is fantastic! The level of care and professionalism provided by the entire crew was top rate.

We had a great flight just wished they had a tv so we can see a movie that would of made my trip excellent.

horrible service, food was an embarrassment, no charging for cellphones, stay away

the food served was an embarrassment. No connection for charging the cellphone... What a crappy airline.

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.

Flight from CHI to PVD was delayed by over 20 hours.

Update to handle the delay was very bad, crews no smiles or welcome or thanks. Don’t care attitude

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

Little warm on the plane and delayed for an hour

Horrible experience with Avianca, they delayed their flight and when we arrived to NYC, AVIANCA took 1 hr y 30 mins to park the airplane and all passenger get off the plane, it made me lost all my trains to get back home and I came back to my place at 3 am instead of 12 am. On the top of that their plane seat are so uncomfortable and is not enough space and killed my legs and knees, Avianca used to be good when it was a Colombian company, now after Brasilian company bought them, their service quality is bad and their flights are delayed and oversold.

It was delayed and I lost my connection flight to Cali and I missed my Mom's funeral and avianca lost my check in luggage

I upgraded to businesses class. Because of that the flight was comfortable.

Avianca has transitioned from full service legacy airline to "low cost" but has now became a strange hybrid (minimum leg space, started offering business class in domestic flights again, charges passenger for printing boarding pass, etc.). National and international coverage and destinations are really wide but service is not at its best

Provide free food and drinks on an international flight. Add updated head rests

Not good, tried to purchase a first class upgrade and they couldn’t get it done. Was super uncomfortable the whole time.

Boarding was late due to the company’s that cleaned the aircraft (very poorly done) and the catering company. The entertainment system was not working for this six hour flight, uncomfortable seats in business (barely any cushion or recline). The airline staff is very good but the planes are horrible and not well maintained.

I handed in my suitcase in perfect condition at SAL Airport. And in MIA Airport I received it with one corner broken and the wheels bent.

I like the crew members they're very friendly. Clean plane. The flight was on time. I dont like the comfort my car seat its better that the plane seats. They charge for everything. This airline was very good. Now it's a low cost airline

No free snacks nor drinks on very short 30min flight. Entertainment system is over wifi to your own phone or tablet, which is good but often a show or movie just stops and refuses to continue

Everything you need to know for your flight from Cali to Chicago

Information on your arrival and departure airports