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Cheap flights from Cali to Chicago from $269

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Cali to Chicago departing on 9/12. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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.
Copa Airlines Logo
12:06 pm - 4:00 am
CLO
-
ORD
15h 54m
1 stop
Copa Airlines Logo
1:20 am - 2:12 pm
ORD
-
CLO
12h 52m
1 stop
$467Copa Airlines
Thu, Jul 9 - Thu, Aug 6
Avianca Logo
9:55 pm - 9:20 pm
CLO
-
ORD
23h 25m
1 stop
Avianca Logo
11:20 pm - 10:20 am
ORD
-
CLO
11h 00m
1 stop
$468Avianca
Mon, Jul 13 - Fri, Jul 31
Avianca Logo
8:25 am - 9:20 pm
CLO
-
ORD
12h 55m
1 stop
Avianca Logo
11:20 pm - 12:00 pm
ORD
-
CLO
12h 40m
1 stop
$476Avianca
Thu, Jul 16 - Thu, Jul 23
Avianca Logo
8:00 am - 9:20 pm
CLO
-
ORD
13h 20m
1 stop
Avianca Logo
11:20 pm - 10:20 am
ORD
-
CLO
11h 00m
1 stop
$477Avianca
Thu, Jul 16 - Thu, Jul 23
Avianca Logo
8:25 am - 9:20 pm
CLO
-
ORD
12h 55m
1 stop
Avianca Logo
11:20 pm - 12:00 pm
ORD
-
CLO
12h 40m
1 stop
$479Avianca
Thu, Jul 16 - Thu, Jul 23
Avianca Logo
9:45 am - 9:20 pm
CLO
-
ORD
11h 35m
1 stop
Avianca Logo
11:20 pm - 12:25 pm
ORD
-
CLO
13h 05m
1 stop
$481Avianca
Mon, Sep 14 - Tue, Oct 6
Avianca Logo
8:25 am - 9:20 pm
CLO
-
ORD
12h 55m
1 stop
Avianca Logo
11:20 pm - 10:20 am
ORD
-
CLO
11h 00m
1 stop
$483Avianca
Thu, Jul 16 - Thu, Jul 23
American Airlines Logo
2:20 pm - 7:29 am
CLO
-
ORD
17h 09m
1 stop
American Airlines Logo
5:00 am - 1:00 pm
ORD
-
CLO
8h 00m
1 stop
$490American Airlines
Mon, Sep 14 - Tue, Oct 6
Copa Airlines Logo
12:08 pm - 1:59 pm
CLO
-
ORD
25h 51m
1 stop
Copa Airlines Logo
3:21 pm - 11:08 am
ORD
-
CLO
19h 47m
1 stop
$491Copa Airlines
Tue, Aug 4 - Mon, Aug 31
American Airlines Logo
11:59 pm - 9:08 am
CLO
-
ORD
9h 09m
1 stop
American Airlines Logo
5:59 pm - 1:17 pm
ORD
-
CLO
19h 18m
1 stop
$493American Airlines
Fri, Jul 17 - Sat, Jul 25

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American Airlines flights from Cali to Chicago

Our best American Airlines deals on Cali to Chicago flight tickets
American Airlines
Sep 14
CLO2:20 pmCali Alfonso B. Aragon Intl
17h 09m
1 stop
ORD7:29 amChicago O'Hare Intl
Oct 6
ORD5:00 amChicago O'Hare Intl
8h 00m
1 stop
CLO1:00 pmCali Alfonso B. Aragon Intl
$490
American Airlines
Jul 17
CLO11:59 pmCali Alfonso B. Aragon Intl
9h 09m
1 stop
ORD9:08 amChicago O'Hare Intl
Jul 25
ORD5:59 pmChicago O'Hare Intl
19h 18m
1 stop
CLO1:17 pmCali Alfonso B. Aragon Intl
$493
American Airlines
Sep 14
CLO2:20 pmCali Alfonso B. Aragon Intl
17h 33m
2 stops
ORD7:53 amChicago O'Hare Intl
Oct 6
ORD5:00 amChicago O'Hare Intl
8h 00m
1 stop
CLO1:00 pmCali Alfonso B. Aragon Intl
$494

Avianca flights from Cali to Chicago

Our best Avianca deals on Cali to Chicago flight tickets
Avianca
Jul 13
CLO9:55 pmCali Alfonso B. Aragon Intl
23h 25m
1 stop
ORD9:20 pmChicago O'Hare Intl
Jul 31
ORD11:20 pmChicago O'Hare Intl
11h 00m
1 stop
CLO10:20 amCali Alfonso B. Aragon Intl
$468
Avianca
Jul 16
CLO8:25 amCali Alfonso B. Aragon Intl
12h 55m
1 stop
ORD9:20 pmChicago O'Hare Intl
Jul 23
ORD11:20 pmChicago O'Hare Intl
12h 40m
1 stop
CLO12:00 pmCali Alfonso B. Aragon Intl
$476
Avianca
Jul 16
CLO8:00 amCali Alfonso B. Aragon Intl
13h 20m
1 stop
ORD9:20 pmChicago O'Hare Intl
Jul 23
ORD11:20 pmChicago O'Hare Intl
11h 00m
1 stop
CLO10:20 amCali Alfonso B. Aragon Intl
$477

momondo Fare Finder

 
Customize your flight search to find flights from Cali to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated June 11, 2026.
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 - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Thu 7/9

12:06 pm-4:00 am

1 stop15h 54m

Chicago O'Hare Intl

Thu 8/6

1:20 am-2:12 pm

1 stop12h 52m

$467

CaliChicago

CLO - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Mon 7/13

9:55 pm-9:20 pm

1 stop23h 25m

Chicago O'Hare Intl

Fri 7/31

11:20 pm-10:20 am

1 stop11h 00m

$468

CaliChicago

CLO - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Thu 7/16

8:25 am-9:20 pm

1 stop12h 55m

Chicago O'Hare Intl

Thu 7/23

11:20 pm-12:00 pm

1 stop12h 40m

$476

CaliChicago

CLO - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Thu 7/16

8:00 am-9:20 pm

1 stop13h 20m

Chicago O'Hare Intl

Thu 7/23

11:20 pm-10:20 am

1 stop11h 00m

$477

CaliChicago

CLO - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Thu 7/16

8:25 am-9:20 pm

1 stop12h 55m

Chicago O'Hare Intl

Thu 7/23

11:20 pm-12:00 pm

1 stop12h 40m

$479

CaliChicago

CLO - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Mon 9/14

9:45 am-9:20 pm

1 stop11h 35m

Chicago O'Hare Intl

Tue 10/6

11:20 pm-12:25 pm

1 stop13h 05m

$481
Quickest round-trip

CaliChicago

CLO - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Thu 7/16

8:25 am-9:20 pm

1 stop12h 55m

Chicago O'Hare Intl

Thu 7/23

11:20 pm-10:20 am

1 stop11h 00m

$483

CaliChicago

CLO - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Mon 9/14

2:20 pm-7:29 am

1 stop17h 09m

Chicago O'Hare Intl

Tue 10/6

5:00 am-1:00 pm

1 stop8h 00m

$490

CaliChicago

CLO - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Tue 8/4

12:08 pm-1:59 pm

1 stop25h 51m

Chicago O'Hare Intl

Mon 8/31

3:21 pm-11:08 am

1 stop19h 47m

$491

CaliChicago

CLO - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Fri 7/17

11:59 pm-9:08 am

1 stop9h 09m

Chicago O'Hare Intl

Sat 7/25

5:59 pm-1:17 pm

1 stop19h 18m

$493

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?

What is the cheapest month to fly to Chicago?

The month of April is, on average, the cheapest month to fly to Chicago from Cali, with most prices found around $201. If you’re not able to fly to Chicago in April, then December is your next best option. Flight prices from Cali to Chicago during December average around $206.

Can stopping save me money on Cali to Chicago flights?

You could potentially save up to 18% 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 June 2026, prices for Cali to Chicago flights are approximately 161% 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

Fastest flight time

14h 21m

Direct flights

None
The fastest flight from Cali to Chicago takes 14h 21m
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. 14h 21m 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
Copa AirlinesPriceFrom $414Free CancellationRating
7.5
1,569 reviews
Search Copa Airlines flights
AviancaPriceFrom $427Free CancellationRating
6.5
2,535 reviews
Search Avianca flights

Traveling to a place near Chicago?

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

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport