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Cheap flights from Cali to Chicago from $203

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 1/26. 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
0 bags

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Find the cheapest flights from Cali to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Spirit Airlines Logo
3:22 pm - 11:46 pm
CLO
-
ORD
9h 24m1 stop
Spirit Airlines Logo
8:43 pm - 2:15 pm
ORD
-
CLO
16h 32m1 stop
$303Spirit Airlines
Thu, Jan 22 - Thu, Jan 29
Copa Airlines Logo
5:00 am - 1:58 pm
CLO
-
ORD
8h 58m1 stop
Copa Airlines Logo
3:21 pm - 11:36 pm
ORD
-
CLO
8h 15m1 stop
$324Copa Airlines
Wed, Apr 22 - Wed, Apr 29
Copa Airlines Logo
3:11 pm - 12:04 am
CLO
-
ORD
9h 53m1 stop
Copa Airlines Logo
2:22 pm - 11:36 pm
ORD
-
CLO
8h 14m1 stop
$348Copa Airlines
Wed, Feb 11 - Wed, Feb 18
Copa Airlines Logo
5:03 am - 12:31 pm
CLO
-
ORD
8h 28m1 stop
Copa Airlines Logo
7:34 am - 11:36 pm
ORD
-
CLO
15h 02m1 stop
$349Copa Airlines
Wed, Feb 11 - Wed, Feb 18
LATAM Airlines Logo
9:50 pm - 7:01 pm
CLO
-
ORD
21h 11m2 stops
LATAM Airlines Logo
6:00 am - 6:05 pm
ORD
-
CLO
12h 05m2 stops
$351LATAM Airlines
Wed, Apr 22 - Wed, Apr 29
Spirit Airlines Logo
3:22 pm - 2:17 pm
CLO
-
ORD
23h 55m2 stops
Spirit Airlines Logo
8:43 pm - 2:15 pm
ORD
-
CLO
16h 32m1 stop
$365Spirit Airlines
Thu, Jan 22 - Thu, Jan 29
Multiple Airlines Logo
12:40 pm - 8:20 pm
CLO
-
ORD
8h 40m1 stop
Multiple Airlines Logo
3:26 pm - 12:30 am
ORD
-
CLO
32h 04m1 stop
$368Multiple Airlines
Thu, Dec 18 - Thu, Jan 1
Multiple Airlines Logo
12:40 pm - 8:20 pm
CLO
-
ORD
8h 40m1 stop
Multiple Airlines Logo
3:26 pm - 12:30 am
ORD
-
CLO
32h 04m1 stop
$373Multiple Airlines
Thu, Dec 18 - Thu, Jan 1
Avianca Logo
9:50 am - 8:20 pm
CLO
-
ORD
11h 30m1 stop
Avianca Logo
11:20 pm - 9:05 am
ORD
-
CLO
9h 45m1 stop
$377Avianca
Fri, Jan 30 - Thu, Mar 12
American Airlines Logo
2:30 pm - 8:48 am
CLO
-
ORD
18h 18m1 stop
American Airlines Logo
2:50 pm - 1:00 pm
ORD
-
CLO
22h 10m1 stop
$394American Airlines
Wed, Apr 22 - Wed, Apr 29

American Airlines flights from Cali to Chicago

Our best American Airlines deals on Cali to Chicago flight tickets
American Airlines
Apr 22
CLO2:30 pmCali Alfonso B. Aragon Intl
18h 18m
1 stop
ORD8:48 amChicago O'Hare Intl
Apr 29
ORD2:50 pmChicago O'Hare Intl
22h 10m
1 stop
CLO1:00 pmCali Alfonso B. Aragon Intl
$394
Find similar
American Airlines
Feb 18
CLO3:20 pmCali Alfonso B. Aragon Intl
18h 42m
1 stop
ORD9:02 amChicago O'Hare Intl
Feb 25
ORD12:32 pmChicago O'Hare Intl
24h 48m
1 stop
CLO2:20 pmCali Alfonso B. Aragon Intl
$397
Find similar
American Airlines
Feb 11
CLO3:20 pmCali Alfonso B. Aragon Intl
17h 00m
2 stops
ORD7:20 amChicago O'Hare Intl
Feb 18
ORD5:26 pmChicago O'Hare Intl
19h 54m
1 stop
CLO2:20 pmCali Alfonso B. Aragon Intl
$398
Find similar

United Airlines flights from Cali to Chicago

Our best United Airlines deals on Cali to Chicago flight tickets
United Airlines
Feb 6
CLO5:03 amCali Alfonso B. Aragon Intl
20h 25m
2 stops
ORD12:28 amChicago O'Hare Intl
Feb 9
ORD7:50 pmChicago O'Hare Intl
21h 00m
2 stops
CLO5:50 pmCali Alfonso B. Aragon Intl
$433
Find similar
United Airlines
Feb 6
CLO8:48 amCali Alfonso B. Aragon Intl
23h 59m
2 stops
ORD7:47 amChicago O'Hare Intl
Feb 9
ORD9:05 pmChicago O'Hare Intl
25h 31m
2 stops
CLO11:36 pmCali Alfonso B. Aragon Intl
$437
Find similar
United Airlines
Feb 6
CLO5:03 amCali Alfonso B. Aragon Intl
16h 10m
2 stops
ORD8:13 pmChicago O'Hare Intl
Feb 9
ORD9:02 amChicago O'Hare Intl
13h 34m
2 stops
CLO11:36 pmCali Alfonso B. Aragon Intl
$438
Find similar

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 December 5, 2025.
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

CaliChicago

CLO - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Thu 1/22

3:22 pm-11:46 pm

1 stop9h 24m

Chicago O'Hare Intl

Thu 1/29

8:43 pm-2:15 pm

1 stop16h 32m

$303

CaliChicago

CLO - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Wed 4/22

5:00 am-1:58 pm

1 stop8h 58m

Chicago O'Hare Intl

Wed 4/29

3:21 pm-11:36 pm

1 stop8h 15m

$324

CaliChicago

CLO - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Wed 2/11

3:11 pm-12:04 am

1 stop9h 53m

Chicago O'Hare Intl

Wed 2/18

2:22 pm-11:36 pm

1 stop8h 14m

$348

CaliChicago

CLO - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Wed 2/11

5:03 am-12:31 pm

1 stop8h 28m

Chicago O'Hare Intl

Wed 2/18

7:34 am-11:36 pm

1 stop15h 02m

$349

CaliChicago

CLO - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Wed 4/22

9:50 pm-7:01 pm

2 stops21h 11m

Chicago O'Hare Intl

Wed 4/29

6:00 am-6:05 pm

2 stops12h 05m

$351

CaliChicago

CLO - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Thu 1/22

3:22 pm-2:17 pm

2 stops23h 55m

Chicago O'Hare Intl

Thu 1/29

8:43 pm-2:15 pm

1 stop16h 32m

$365

CaliChicago

CLO - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Thu 12/18

12:40 pm-8:20 pm

1 stop8h 40m

Chicago O'Hare Intl

Thu 1/1

3:26 pm-12:30 am

1 stop32h 04m

$368

CaliChicago

CLO - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Thu 12/18

12:40 pm-8:20 pm

1 stop8h 40m

Chicago O'Hare Intl

Thu 1/1

3:26 pm-12:30 am

1 stop32h 04m

$373

CaliChicago

CLO - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Fri 1/30

9:50 am-8:20 pm

1 stop11h 30m

Chicago O'Hare Intl

Thu 3/12

11:20 pm-9:05 am

1 stop9h 45m

$377

CaliChicago

CLO - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Wed 4/22

2:30 pm-8:48 am

1 stop18h 18m

Chicago O'Hare Intl

Wed 4/29

2:50 pm-1:00 pm

1 stop22h 10m

$394

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 September is, on average, the cheapest month to fly to Chicago from Cali, with most prices found around $412. If you’re not able to fly to Chicago in September, then November is your next best option. Flight prices from Cali to Chicago during November average around $415.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $466. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Cali to Chicago for around $615.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Cali to Chicago during this time can be as low as $425. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $561.

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 $452 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 December 2025, prices for Cali to Chicago flights are approximately 26% 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

8h 28m

Direct flights

None
The fastest flight from Cali to Chicago takes 8h 28m
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. 8h 28m 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
6.6
2,479 reviews
Search Avianca flights
American AirlinesPriceFrom $403Free CancellationRating
7.2
11,044 reviews
Search American Airlines flights
Copa AirlinesPriceFrom $414Free CancellationRating
7.6
1,556 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
Schererville
Valparaiso
Crown Point
Munster
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