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Cheap flights from Cali to Chicago from $303

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 9/8. 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.
American Airlines Logo
3:20 pm - 12:38 am
CLO
-
ORD
10h 18m
1 stop
American Airlines Logo
7:10 pm - 2:20 pm
ORD
-
CLO
18h 10m
1 stop
$441American Airlines
Mon, Dec 21 - Sun, Jan 24
American Airlines Logo
3:20 pm - 7:42 am
CLO
-
ORD
17h 22m
1 stop
American Airlines Logo
8:55 pm - 2:20 pm
ORD
-
CLO
16h 25m
2 stops
$446American Airlines
Mon, Dec 21 - Sun, Jan 24
LATAM Airlines Logo
8:55 am - 11:57 pm
CLO
-
ORD
15h 02m
2 stops
LATAM Airlines Logo
5:30 am - 12:45 am
ORD
-
CLO
19h 15m
2 stops
$454LATAM Airlines
Wed, Sep 2 - Sun, Sep 6
LATAM Airlines Logo
10:40 am - 9:25 am
CLO
-
ORD
22h 45m
2 stops
LATAM Airlines Logo
5:30 am - 6:10 am
ORD
-
CLO
24h 40m
2 stops
$456LATAM Airlines
Tue, Sep 15 - Sun, Oct 4
LATAM Airlines Logo
5:25 am - 6:49 pm
CLO
-
ORD
13h 24m
2 stops
LATAM Airlines Logo
5:30 am - 12:45 am
ORD
-
CLO
19h 15m
2 stops
$457LATAM Airlines
Wed, Sep 2 - Sun, Sep 6
Copa Airlines Logo
12:08 pm - 1:02 am
CLO
-
ORD
12h 54m
1 stop
Copa Airlines Logo
3:20 pm - 2:12 pm
ORD
-
CLO
22h 52m
1 stop
$471Copa Airlines
Mon, Sep 21 - Sat, Sep 26
Avianca Logo
11:10 am - 9:20 pm
CLO
-
ORD
10h 10m
1 stop
Avianca Logo
11:20 pm - 12:25 pm
ORD
-
CLO
13h 05m
1 stop
$485Avianca
Tue, Sep 1 - Sat, Sep 5
Avianca Logo
11:10 am - 9:20 pm
CLO
-
ORD
10h 10m
1 stop
Avianca Logo
11:20 pm - 9:00 am
ORD
-
CLO
9h 40m
1 stop
$486Avianca
Thu, Sep 3 - Thu, Sep 10
Avianca Logo
10:15 am - 9:20 pm
CLO
-
ORD
11h 05m
1 stop
Avianca Logo
11:20 pm - 12:00 pm
ORD
-
CLO
12h 40m
1 stop
$487Avianca
Thu, Sep 3 - Thu, Sep 10
Copa Airlines Logo
12:08 pm - 1:59 pm
CLO
-
ORD
25h 51m
1 stop
Copa Airlines Logo
8:01 am - 5:37 pm
ORD
-
CLO
9h 36m
1 stop
$488Copa Airlines
Thu, Sep 3 - Mon, Oct 5

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Avianca flights from Cali to Chicago

Our best Avianca deals on Cali to Chicago flight tickets
Avianca
Sep 1
CLO11:10 amCali Alfonso B. Aragon Intl
10h 10m
1 stop
ORD9:20 pmChicago O'Hare Intl
Sep 5
ORD11:20 pmChicago O'Hare Intl
13h 05m
1 stop
CLO12:25 pmCali Alfonso B. Aragon Intl
$485
Avianca
Sep 2
CLO11:10 amCali Alfonso B. Aragon Intl
10h 10m
1 stop
ORD9:20 pmChicago O'Hare Intl
Sep 6
ORD11:20 pmChicago O'Hare Intl
12h 40m
1 stop
CLO12:00 pmCali Alfonso B. Aragon Intl
$486
Avianca
Sep 3
CLO10:15 amCali Alfonso B. Aragon Intl
11h 05m
1 stop
ORD9:20 pmChicago O'Hare Intl
Sep 10
ORD11:20 pmChicago O'Hare Intl
12h 40m
1 stop
CLO12:00 pmCali Alfonso B. Aragon Intl
$487

Copa Airlines flights from Cali to Chicago

Our best Copa Airlines deals on Cali to Chicago flight tickets
Copa Airlines
Sep 21
CLO12:08 pmCali Alfonso B. Aragon Intl
12h 54m
1 stop
ORD1:02 amChicago O'Hare Intl
Sep 26
ORD3:20 pmChicago O'Hare Intl
22h 52m
1 stop
CLO2:12 pmCali Alfonso B. Aragon Intl
$471
Copa Airlines
Sep 3
CLO12:08 pmCali Alfonso B. Aragon Intl
25h 51m
1 stop
ORD1:59 pmChicago O'Hare Intl
Oct 5
ORD8:01 amChicago O'Hare Intl
9h 36m
1 stop
CLO5:37 pmCali Alfonso B. Aragon Intl
$488
Copa Airlines
Sep 1
CLO12:08 pmCali Alfonso B. Aragon Intl
25h 51m
1 stop
ORD1:59 pmChicago O'Hare Intl
Nov 18
ORD2:13 pmChicago O'Hare Intl
22h 53m
1 stop
CLO2:06 pmCali Alfonso B. Aragon Intl
$495

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 July 26, 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

Mon 12/21

3:20 pm-12:38 am

1 stop10h 18m

Chicago O'Hare Intl

Sun 1/24

7:10 pm-2:20 pm

1 stop18h 10m

$441

CaliChicago

CLO - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Mon 12/21

3:20 pm-7:42 am

1 stop17h 22m

Chicago O'Hare Intl

Sun 1/24

8:55 pm-2:20 pm

2 stops16h 25m

$446

CaliChicago

CLO - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Wed 9/2

8:55 am-11:57 pm

2 stops15h 02m

Chicago O'Hare Intl

Sun 9/6

5:30 am-12:45 am

2 stops19h 15m

$454

CaliChicago

CLO - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Tue 9/15

10:40 am-9:25 am

2 stops22h 45m

Chicago O'Hare Intl

Sun 10/4

5:30 am-6:10 am

2 stops24h 40m

$456

CaliChicago

CLO - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Wed 9/2

5:25 am-6:49 pm

2 stops13h 24m

Chicago O'Hare Intl

Sun 9/6

5:30 am-12:45 am

2 stops19h 15m

$457

CaliChicago

CLO - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Mon 9/21

12:08 pm-1:02 am

1 stop12h 54m

Chicago O'Hare Intl

Sat 9/26

3:20 pm-2:12 pm

1 stop22h 52m

$471

CaliChicago

CLO - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Tue 9/1

11:10 am-9:20 pm

1 stop10h 10m

Chicago O'Hare Intl

Sat 9/5

11:20 pm-12:25 pm

1 stop13h 05m

$485
Quickest round-trip

CaliChicago

CLO - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Thu 9/3

11:10 am-9:20 pm

1 stop10h 10m

Chicago O'Hare Intl

Thu 9/10

11:20 pm-9:00 am

1 stop9h 40m

$486

CaliChicago

CLO - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Thu 9/3

10:15 am-9:20 pm

1 stop11h 05m

Chicago O'Hare Intl

Thu 9/10

11:20 pm-12:00 pm

1 stop12h 40m

$487

CaliChicago

CLO - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Thu 9/3

12:08 pm-1:59 pm

1 stop25h 51m

Chicago O'Hare Intl

Mon 10/5

8:01 am-5:37 pm

1 stop9h 36m

$488

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 $530 to $666.
The lowest price recently found on this route was $441.

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 $426.

Can stopping save me money on Cali to Chicago flights?

You could potentially save up to 2% 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 July 2026, prices for Cali to Chicago flights are approximately 42% 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

11h 08m

Direct flights

None
The fastest flight from Cali to Chicago takes 11h 08m
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. 11h 08m 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
7.6
1,561 reviews
Search Copa Airlines flights
AviancaPriceFrom $427Free CancellationRating
6.5
2,519 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
Portage
Benton Harbor
Lansing
Saint Joseph
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

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