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Cheap flights from Cali to Chicago from $231

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 4/22. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Spirit Airlines Logo
1:53 pm - 12:24 am
CLO
-
ORD
10h 31m
1 stop
Spirit Airlines Logo
7:15 pm - 12:58 pm
ORD
-
CLO
17h 43m
1 stop
$340Spirit Airlines
Fri, Apr 17 - Fri, Apr 24
Multiple Airlines Logo
9:45 am - 12:24 am
CLO
-
ORD
14h 39m
2 stops
Multiple Airlines Logo
5:05 am - 12:58 pm
ORD
-
CLO
7h 53m
1 stop
$387Multiple Airlines
Thu, May 14 - Mon, Jun 1
Multiple Airlines Logo
8:06 pm - 12:24 am
CLO
-
ORD
28h 18m
2 stops
Multiple Airlines Logo
5:05 am - 12:58 pm
ORD
-
CLO
7h 53m
1 stop
$390Multiple Airlines
Tue, Apr 21 - Sat, Apr 25
Spirit Airlines Logo
1:53 pm - 9:12 pm
CLO
-
ORD
31h 19m
2 stops
Spirit Airlines Logo
7:15 pm - 12:58 pm
ORD
-
CLO
17h 43m
1 stop
$398Spirit Airlines
Fri, Apr 17 - Fri, Apr 24
Multiple Airlines Logo
1:53 pm - 12:24 am
CLO
-
ORD
10h 31m
1 stop
Multiple Airlines Logo
11:20 pm - 12:25 pm
ORD
-
CLO
13h 05m
1 stop
$407Multiple Airlines
Wed, Jun 3 - Tue, Jun 9
American Airlines Logo
2:15 pm - 7:31 am
CLO
-
ORD
17h 16m
2 stops
American Airlines Logo
9:01 pm - 1:08 pm
ORD
-
CLO
16h 07m
2 stops
$410American Airlines
Fri, Apr 17 - Fri, Apr 24
American Airlines Logo
2:15 pm - 12:25 am
CLO
-
ORD
10h 10m
1 stop
American Airlines Logo
5:00 am - 1:08 pm
ORD
-
CLO
8h 08m
1 stop
$413American Airlines
Tue, Apr 21 - Tue, Apr 28
Copa Airlines Logo
8:46 am - 1:13 am
CLO
-
ORD
16h 27m
1 stop
Copa Airlines Logo
8:06 am - 5:36 pm
ORD
-
CLO
9h 30m
1 stop
$415Copa Airlines
Wed, Apr 22 - Wed, Apr 29
American Airlines Logo
2:15 pm - 12:25 am
CLO
-
ORD
10h 10m
1 stop
American Airlines Logo
9:01 pm - 1:08 pm
ORD
-
CLO
16h 07m
2 stops
$417American Airlines
Tue, Apr 21 - Sat, Apr 25
Copa Airlines Logo
8:46 am - 1:13 am
CLO
-
ORD
16h 27m
1 stop
Copa Airlines Logo
8:06 am - 5:36 pm
ORD
-
CLO
9h 30m
1 stop
$425Copa Airlines
Mon, Apr 13 - Sat, Apr 18

Copa Airlines flights from Cali to Chicago

Our best Copa Airlines deals on Cali to Chicago flight tickets
Copa Airlines
Apr 13
CLO8:46 amCali Alfonso B. Aragon Intl
16h 27m
1 stop
ORD1:13 amChicago O'Hare Intl
Apr 18
ORD8:06 amChicago O'Hare Intl
9h 30m
1 stop
CLO5:36 pmCali Alfonso B. Aragon Intl
$425
Copa Airlines
Apr 22
CLO8:46 amCali Alfonso B. Aragon Intl
16h 27m
1 stop
ORD1:13 amChicago O'Hare Intl
Apr 29
ORD3:05 pmChicago O'Hare Intl
8h 31m
1 stop
CLO11:36 pmCali Alfonso B. Aragon Intl
$437
Copa Airlines
Apr 18
CLO8:46 amCali Alfonso B. Aragon Intl
16h 27m
1 stop
ORD1:13 amChicago O'Hare Intl
Apr 26
ORD8:06 amChicago O'Hare Intl
9h 30m
1 stop
CLO5:36 pmCali Alfonso B. Aragon Intl
$447

Avianca flights from Cali to Chicago

Our best Avianca deals on Cali to Chicago flight tickets
Avianca
Apr 19
CLO8:00 amCali Alfonso B. Aragon Intl
13h 20m
1 stop
ORD9:20 pmChicago O'Hare Intl
Apr 26
ORD11:20 pmChicago O'Hare Intl
9h 40m
1 stop
CLO9:00 amCali Alfonso B. Aragon Intl
$438
Avianca
Apr 19
CLO8:00 amCali Alfonso B. Aragon Intl
13h 20m
1 stop
ORD9:20 pmChicago O'Hare Intl
Apr 25
ORD11:20 pmChicago O'Hare Intl
13h 55m
1 stop
CLO1:15 pmCali Alfonso B. Aragon Intl
$439
Avianca
Apr 18
CLO8:25 amCali Alfonso B. Aragon Intl
12h 55m
1 stop
ORD9:20 pmChicago O'Hare Intl
Apr 26
ORD11:20 pmChicago O'Hare Intl
13h 05m
1 stop
CLO12:25 pmCali Alfonso B. Aragon Intl
$440

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 March 8, 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

Fri 4/17

1:53 pm-12:24 am

1 stop10h 31m

Chicago O'Hare Intl

Fri 4/24

7:15 pm-12:58 pm

1 stop17h 43m

$340

CaliChicago

CLO - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Thu 5/14

9:45 am-12:24 am

2 stops14h 39m

Chicago O'Hare Intl

Mon 6/1

5:05 am-12:58 pm

1 stop7h 53m

$387

CaliChicago

CLO - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Tue 4/21

8:06 pm-12:24 am

2 stops28h 18m

Chicago O'Hare Intl

Sat 4/25

5:05 am-12:58 pm

1 stop7h 53m

$390

CaliChicago

CLO - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Fri 4/17

1:53 pm-9:12 pm

2 stops31h 19m

Chicago O'Hare Intl

Fri 4/24

7:15 pm-12:58 pm

1 stop17h 43m

$398

CaliChicago

CLO - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Wed 6/3

1:53 pm-12:24 am

1 stop10h 31m

Chicago O'Hare Intl

Tue 6/9

11:20 pm-12:25 pm

1 stop13h 05m

$407

CaliChicago

CLO - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Fri 4/17

2:15 pm-7:31 am

2 stops17h 16m

Chicago O'Hare Intl

Fri 4/24

9:01 pm-1:08 pm

2 stops16h 07m

$410
Quickest round-trip

CaliChicago

CLO - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Tue 4/21

2:15 pm-12:25 am

1 stop10h 10m

Chicago O'Hare Intl

Tue 4/28

5:00 am-1:08 pm

1 stop8h 08m

$413

CaliChicago

CLO - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Wed 4/22

8:46 am-1:13 am

1 stop16h 27m

Chicago O'Hare Intl

Wed 4/29

8:06 am-5:36 pm

1 stop9h 30m

$415

CaliChicago

CLO - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Tue 4/21

2:15 pm-12:25 am

1 stop10h 10m

Chicago O'Hare Intl

Sat 4/25

9:01 pm-1:08 pm

2 stops16h 07m

$417

CaliChicago

CLO - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Mon 4/13

8:46 am-1:13 am

1 stop16h 27m

Chicago O'Hare Intl

Sat 4/18

8:06 am-5:36 pm

1 stop9h 30m

$425

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 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 $399. If you’re not able to fly to Chicago in February, then November is your next best option. Flight prices from Cali to Chicago during November average around $415.

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Cali when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $476 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Cali for as low as $308 on momondo.

How have Cali to Chicago flight prices changed over time?

As of March 2026, prices for Cali to Chicago flights are approximately 74% 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

10h 10m

Direct flights

None
The fastest flight from Cali to Chicago takes 10h 10m
There are no direct flights from Cali to Chicago. There are no popular flight routes from Cali to Chicago.
Search flight deals

  • 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. 10h 10m 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 $330Free CancellationRating
6.5
2,494 reviews
Search Avianca flights
American AirlinesPriceFrom $403Free CancellationRating
7.1
11,399 reviews
Search American Airlines flights
Copa AirlinesPriceFrom $414Free CancellationRating
7.5
1,565 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
Benton Harbor
Saint Joseph
Portage
Lansing
Valparaiso
Schererville
Munster
Crown Point
Chesterton
Monticello
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