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Cheap flights from Cali to Chicago from $311

1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Cali to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
6:42 am - 11:13 amCLO  Cali Alfonso B. Aragon Intl-ORD Chicago O'Hare Intl
29h 31m2 stops Medellín Jose Maria Cordova Intl Guadalajara Miguel Hidal
Multiple Airlines Logo
12:53 pm - 9:09 pmORD  Chicago O'Hare Intl-CLO Cali Alfonso B. Aragon Intl
31h 16m2 stops Guadalajara Miguel Hidal Bogotá El Dorado
$514Multiple Airlines
Wed, Mar 3 - Wed, Mar 10
American Airlines Logo
3:33 pm - 9:30 amCLO  Cali Alfonso B. Aragon Intl-ORD Chicago O'Hare Intl
18h 57m1 stop Miami
American Airlines Logo
7:47 pm - 2:34 pmORD  Chicago O'Hare Intl-CLO Cali Alfonso B. Aragon Intl
17h 47m1 stop Miami
$534American Airlines
Wed, Feb 10 - Wed, Feb 17
American Airlines Logo
3:34 pm - 9:30 amCLO  Cali Alfonso B. Aragon Intl-ORD Chicago O'Hare Intl
18h 56m1 stop Miami
American Airlines Logo
7:47 pm - 2:34 pmORD  Chicago O'Hare Intl-CLO Cali Alfonso B. Aragon Intl
17h 47m1 stop Miami
$534American Airlines
Wed, Feb 17 - Wed, Feb 24
American Airlines Logo
7:30 am - 9:15 pmCLO  Cali Alfonso B. Aragon Intl-ORD Chicago O'Hare Intl
14h 45m1 stop Miami
American Airlines Logo
6:59 am - 9:37 pmORD  Chicago O'Hare Intl-CLO Cali Alfonso B. Aragon Intl
13h 38m1 stop Miami
$539American Airlines
Fri, Dec 18 - Fri, Jan 1
Copa Airlines Logo
11:58 am - 12:44 amCLO  Cali Alfonso B. Aragon Intl-ORD Chicago O'Hare Intl
12h 46m1 stop Panama City Tocumen Intl
Copa Airlines Logo
3:13 pm - 5:19 pmORD  Chicago O'Hare Intl-CLO Cali Alfonso B. Aragon Intl
26h 06m1 stop Panama City Tocumen Intl
$569Copa Airlines
Thu, Apr 8 - Sun, Apr 11
Copa Airlines Logo
8:41 am - 12:07 amCLO  Cali Alfonso B. Aragon Intl-ORD Chicago O'Hare Intl
16h 26m1 stop Panama City Tocumen Intl
Copa Airlines Logo
7:08 am - 10:10 amORD  Chicago O'Hare Intl-CLO Cali Alfonso B. Aragon Intl
26h 02m1 stop Panama City Tocumen Intl
$569Copa Airlines
Fri, Jan 29 - Mon, Mar 8
Copa Airlines Logo
12:05 pm - 12:11 amCLO  Cali Alfonso B. Aragon Intl-ORD Chicago O'Hare Intl
13h 06m1 stop Panama City Tocumen Intl
Copa Airlines Logo
2:13 pm - 10:57 amORD  Chicago O'Hare Intl-CLO Cali Alfonso B. Aragon Intl
19h 44m1 stop Panama City Tocumen Intl
$569Copa Airlines
Thu, Nov 12 - Mon, Nov 16
Avianca Logo
11:10 am - 9:20 pmCLO  Cali Alfonso B. Aragon Intl-ORD Chicago O'Hare Intl
10h 10m1 stop Bogotá El Dorado
Avianca Logo
11:20 pm - 12:25 pmORD  Chicago O'Hare Intl-CLO Cali Alfonso B. Aragon Intl
13h 05m1 stop Bogotá El Dorado
$616Avianca
Wed, Mar 31 - Wed, Apr 7
Avianca Logo
8:20 pm - 8:30 pmCLO  Cali Alfonso B. Aragon Intl-ORD Chicago O'Hare Intl
25h 10m1 stop Bogotá El Dorado
Avianca Logo
10:30 pm - 11:30 amORD  Chicago O'Hare Intl-CLO Cali Alfonso B. Aragon Intl
12h 00m1 stop Bogotá El Dorado
$692Avianca
Thu, Jan 14 - Sun, Jan 24
Avianca Logo
5:50 pm - 8:30 pmCLO  Cali Alfonso B. Aragon Intl-ORD Chicago O'Hare Intl
27h 40m1 stop Bogotá El Dorado
Avianca Logo
10:30 pm - 9:00 amORD  Chicago O'Hare Intl-CLO Cali Alfonso B. Aragon Intl
9h 30m1 stop Bogotá El Dorado
$702Avianca
Sun, Dec 20 - Wed, Jan 6

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United Airlines flights from Cali to Chicago

Our best United Airlines deals on Cali to Chicago flight tickets
United Airlines
Jan 20
CLO4:38 amCali Alfonso B. Aragon Intl
15h 00m
2 stops
ORD6:38 pmChicago O'Hare Intl
Jan 31
ORD7:50 pmChicago O'Hare Intl
20h 43m
2 stops
CLO5:33 pmCali Alfonso B. Aragon Intl
$606
United Airlines
Nov 7
CLO12:05 pmCali Alfonso B. Aragon Intl
23h 06m
2 stops
ORD10:11 amChicago O'Hare Intl
Nov 11
ORD9:35 pmChicago O'Hare Intl
24h 57m
2 stops
CLO11:32 pmCali Alfonso B. Aragon Intl
$607
United Airlines
Nov 7
CLO12:05 pmCali Alfonso B. Aragon Intl
13h 40m
2 stops
ORD12:45 amChicago O'Hare Intl
Nov 11
ORD7:55 pmChicago O'Hare Intl
26h 37m
2 stops
CLO11:32 pmCali Alfonso B. Aragon Intl
$608

Copa Airlines flights from Cali to Chicago

Our best Copa Airlines deals on Cali to Chicago flight tickets
Copa Airlines
Nov 12
CLO12:05 pmCali Alfonso B. Aragon Intl
13h 06m
1 stop
ORD12:11 amChicago O'Hare Intl
Nov 16
ORD2:13 pmChicago O'Hare Intl
19h 44m
1 stop
CLO10:57 amCali Alfonso B. Aragon Intl
$569
Copa Airlines
Jan 21
CLO12:03 pmCali Alfonso B. Aragon Intl
13h 04m
1 stop
ORD12:07 amChicago O'Hare Intl
Jan 25
ORD7:35 amChicago O'Hare Intl
26h 25m
1 stop
CLO11:00 amCali Alfonso B. Aragon Intl
$570
Copa Airlines
Oct 28
CLO4:40 amCali Alfonso B. Aragon Intl
20h 25m
1 stop
ORD1:05 amChicago O'Hare Intl
Nov 4
ORD2:13 pmChicago O'Hare Intl
25h 51m
1 stop
CLO5:04 pmCali Alfonso B. Aragon Intl
$574

momondo Fare Finder

 
Use the filters below to find and compare flights from Cali to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

CaliChicago

CLO Cali Alfonso B. Aragon Intl - ORD Chicago O'Hare Intl

CLOORD

Cali Alfonso B. Aragon Intl

Wed 3/3

6:42 am-11:13 am

2 stops29h 31m

Chicago O'Hare Intl

Wed 3/10

12:53 pm-9:09 pm

2 stops31h 16m

$514

CaliChicago

CLO Cali Alfonso B. Aragon Intl - ORD Chicago O'Hare Intl

CLOORD

Cali Alfonso B. Aragon Intl

Wed 2/10

3:33 pm-9:30 am

1 stop18h 57m

Chicago O'Hare Intl

Wed 2/17

7:47 pm-2:34 pm

1 stop17h 47m

$534

CaliChicago

CLO Cali Alfonso B. Aragon Intl - ORD Chicago O'Hare Intl

CLOORD

Cali Alfonso B. Aragon Intl

Wed 2/17

3:34 pm-9:30 am

1 stop18h 56m

Chicago O'Hare Intl

Wed 2/24

7:47 pm-2:34 pm

1 stop17h 47m

$534

CaliChicago

CLO Cali Alfonso B. Aragon Intl - ORD Chicago O'Hare Intl

CLOORD

Cali Alfonso B. Aragon Intl

Fri 12/18

7:30 am-9:15 pm

1 stop14h 45m

Chicago O'Hare Intl

Fri 1/1

6:59 am-9:37 pm

1 stop13h 38m

$539

CaliChicago

CLO Cali Alfonso B. Aragon Intl - ORD Chicago O'Hare Intl

CLOORD

Cali Alfonso B. Aragon Intl

Thu 4/8

11:58 am-12:44 am

1 stop12h 46m

Chicago O'Hare Intl

Sun 4/11

3:13 pm-5:19 pm

1 stop26h 06m

$569

CaliChicago

CLO Cali Alfonso B. Aragon Intl - ORD Chicago O'Hare Intl

CLOORD

Cali Alfonso B. Aragon Intl

Fri 1/29

8:41 am-12:07 am

1 stop16h 26m

Chicago O'Hare Intl

Mon 3/8

7:08 am-10:10 am

1 stop26h 02m

$569

CaliChicago

CLO Cali Alfonso B. Aragon Intl - ORD Chicago O'Hare Intl

CLOORD

Cali Alfonso B. Aragon Intl

Thu 11/12

12:05 pm-12:11 am

1 stop13h 06m

Chicago O'Hare Intl

Mon 11/16

2:13 pm-10:57 am

1 stop19h 44m

$569
Quickest round-trip

CaliChicago

CLO Cali Alfonso B. Aragon Intl - ORD Chicago O'Hare Intl

CLOORD

Cali Alfonso B. Aragon Intl

Wed 3/31

11:10 am-9:20 pm

1 stop10h 10m

Chicago O'Hare Intl

Wed 4/7

11:20 pm-12:25 pm

1 stop13h 05m

$616

CaliChicago

CLO Cali Alfonso B. Aragon Intl - ORD Chicago O'Hare Intl

CLOORD

Cali Alfonso B. Aragon Intl

Thu 1/14

8:20 pm-8:30 pm

1 stop25h 10m

Chicago O'Hare Intl

Sun 1/24

10:30 pm-11:30 am

1 stop12h 00m

$692

CaliChicago

CLO Cali Alfonso B. Aragon Intl - ORD Chicago O'Hare Intl

CLOORD

Cali Alfonso B. Aragon Intl

Sun 12/20

5:50 pm-8:30 pm

1 stop27h 40m

Chicago O'Hare Intl

Wed 1/6

10:30 pm-9:00 am

1 stop9h 30m

$702

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Cali to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Cali and Chicago?

Prices are currently low for flights on this route.

Typical prices usually range from $666 to $691.
The lowest price recently found on this route was $514.

What is the cheapest month to fly to Chicago?

The month of February is, on average, the cheapest month to fly to Chicago from Cali, with most prices found around $416. If you’re not able to fly to Chicago in February, then April is your next best option. Flight prices from Cali to Chicago during April average around $437.

Can stopping save me money on Cali to Chicago flights?

You could potentially save up to 17% on your flight if you consider stops on a Cali to Chicago flight.

How have Cali to Chicago flight prices changed over time?

As of October 2026, prices for Cali to Chicago flights are approximately 39% more expensive when compared to flights at the same time last year.

When to book flights from Cali to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Cali to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Cali to Chicago (CLO to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Cali to Chicago

Best Price Found

$311

Fastest flight time

12h 46m

Direct flights

None
The best one-way flight to Chicago from Cali in the past 72 hours is $311. The best round-trip flight deal from Cali to Chicago found on momondo in the last 72 hours is $514.
The fastest flight from Cali to Chicago takes 12h 46m
There are no direct flights from Cali to Chicago. There are no popular flight routes from Cali to Chicago.
Search flight deals

Frequently asked questions about flying from Cali to Chicago

  • How far is Cali Alfonso B. Aragon Intl to Chicago by plane?

    The straight-line distance from Cali Alfonso B. Aragon Intl to Chicago is 2740.2 mi. 12h 46m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Cali Alfonso B. Aragon Intl Airport to Chicago?

    Prices for flights from Cali Alfonso B. Aragon Intl Airport to Chicago refresh daily.

  • How many operators does momondo search for flights from Cali Alfonso B. Aragon Intl Airport to Chicago?

  • How old do you have to be to fly from Cali Alfonso B. Aragon Intl Airport to Chicago?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Cali Alfonso B. Aragon Intl Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Cali to Chicago?

Best airlines flying from Cali to Chicago

Compare and see reviews for airlines that fly from Cali to Chicago with momondo
Airline
Rating
Free Cancellation
Price
AviancaPriceFrom $465Free CancellationRating
6.5
2,550 reviews
Search Avianca flights
Copa AirlinesPriceFrom $471Free CancellationRating
7.6
1,553 reviews
Search Copa Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Portage
Lansing
Saint Joseph
Benton Harbor
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Cali to Chicago?

It is quick and easy to find Cali to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

Can I find flights from Cali to Chicago with flexible booking policies on momondo?

Flights from Cali to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Cali to Chicago?

Once all potential Cali to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Cali to Chicago right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Cali and alert you when they change.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport