CLO - ORD

$281 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 5/23. 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
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Everything you should know

Cheapest round-trip
$440
Typical prices: $601-$477
American Airlines
Thu 5/28Tue 6/16
CLO - ORD • 1 stop
Cheapest one-way
$281
Typical prices: $267-$331
American Airlines
Sat 5/23
CLO - ORD • 1 stop
Top airlines
American Airlines
Cheapest • from $440 (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 • 8h 59m (one-way)
Insights
Insights
Insights
Insights
When to travel
April
Cheapest • 29% price drop
May
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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

Thu, May 28 - Tue, Jun 16
American Airlines Logo
11:59 pm - 9:10 am
CLO
-
ORD
9h 11m
1 stop
American Airlines Logo
6:00 pm - 1:18 pm
ORD
-
CLO
19h 18m
1 stop
$440American Airlines
Thu, May 28 - Mon, Jun 15
American Airlines Logo
11:59 pm - 9:10 am
CLO
-
ORD
9h 11m
1 stop
American Airlines Logo
6:00 pm - 1:18 pm
ORD
-
CLO
19h 18m
1 stop
$441American Airlines
Thu, May 28 - Tue, Jun 16
American Airlines Logo
11:59 pm - 12:18 pm
CLO
-
ORD
12h 19m
2 stops
American Airlines Logo
6:00 pm - 1:18 pm
ORD
-
CLO
19h 18m
1 stop
$445American Airlines
Tue, Sep 1 - Tue, Sep 8
American Airlines Logo
2:15 pm - 9:00 am
CLO
-
ORD
18h 45m
1 stop
American Airlines Logo
5:44 pm - 1:00 pm
ORD
-
CLO
19h 16m
1 stop
$452American Airlines
Fri, May 22 - Fri, Jun 12
American Airlines Logo
11:59 pm - 7:57 pm
CLO
-
ORD
19h 58m
1 stop
American Airlines Logo
6:10 am - 9:00 pm
ORD
-
CLO
14h 50m
1 stop
$463American Airlines
Tue, Jul 28 - Wed, Aug 19
Copa Airlines Logo
3:10 pm - 4:00 am
CLO
-
ORD
12h 50m
1 stop
Copa Airlines Logo
8:02 am - 5:33 pm
ORD
-
CLO
9h 31m
1 stop
$465Copa Airlines
Mon, Jun 1 - Sat, Jun 13
Copa Airlines Logo
12:06 pm - 4:00 am
CLO
-
ORD
15h 54m
1 stop
Copa Airlines Logo
1:00 am - 2:10 pm
ORD
-
CLO
13h 10m
1 stop
$466Copa Airlines
Fri, May 22 - Fri, Jun 12
American Airlines Logo
11:59 pm - 12:18 pm
CLO
-
ORD
12h 19m
2 stops
American Airlines Logo
6:10 am - 9:00 pm
ORD
-
CLO
14h 50m
1 stop
$467American Airlines
Fri, May 22 - Fri, Jun 12
American Airlines Logo
11:59 pm - 2:20 pm
CLO
-
ORD
14h 21m
2 stops
American Airlines Logo
6:10 am - 9:00 pm
ORD
-
CLO
14h 50m
1 stop
$468American Airlines
Tue, Jun 16 - Thu, Aug 27
American Airlines Logo
11:59 pm - 11:00 am
CLO
-
ORD
11h 01m
1 stop
American Airlines Logo
5:01 am - 9:00 pm
ORD
-
CLO
15h 59m
1 stop
$474American 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.

How much is a round-trip flight from Cali to Chicago O'Hare Intl Airport?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Cali to Chicago O'Hare Intl Airport departing in May.

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 April, where tickets cost $337 (return) on average. On the other hand, the most expensive months are May and December, where the average cost of round-trip tickets is $566 and $552 respectively.

Find deals

Good to know

Low seasonJanuary
Cheapest flight$281
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly with an average 18% increase in price.
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 $281 for a one-way ticket and $440 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?

    Star Alliance is the only airline alliance operating flights between Cali and Chicago.

  • 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 airline flying 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 1584 reviews
6.8Food
8.1Crew
6.8Entertainment
7.8Boarding
7.4Comfort
Airline reviews

Boarding was a mess, they call all priority members without distinction so gold, platinum, silver were all mixed together in a long line which defeats the purpose

10.0 ExcellentAnonymous, Apr 2026
DAV - PTY
Read more Copa Airlines reviews

Boarding was a mess, they call all priority members without distinction so gold, platinum, silver were all mixed together in a long line which defeats the purpose

Entire experience from check in to landing was amazing the flight crew was excellent and friendly. Seats were comfortable.

Do not book it’s a scam! They stole $1200 from me

Flight got delayed; had to go through security three times.

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

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

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.

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

Information on your arrival and departure airports

Cali (CLO)
O'Hare Intl (ORD)