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Cheap flights from Cali to Chicago from $250

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 5/14. 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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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 - 11:47 pm
CLO
-
ORD
9h 25m
1 stop
Spirit Airlines Logo
5:15 am - 2:15 pm
ORD
-
CLO
8h 00m
1 stop
$301Spirit Airlines
Wed, Feb 4 - Mon, Feb 9
Spirit Airlines Logo
3:22 pm - 6:16 pm
CLO
-
ORD
27h 54m
3 stops
Spirit Airlines Logo
5:15 am - 2:15 pm
ORD
-
CLO
8h 00m
1 stop
$350Spirit Airlines
Wed, Feb 4 - Mon, Feb 9
American Airlines Logo
3:20 pm - 12:37 am
CLO
-
ORD
10h 17m
1 stop
American Airlines Logo
6:59 pm - 1:20 pm
ORD
-
CLO
18h 21m
1 stop
$358American Airlines
Thu, Mar 5 - Mon, Mar 9
American Airlines Logo
3:20 pm - 7:24 am
CLO
-
ORD
17h 04m
2 stops
American Airlines Logo
6:59 pm - 1:20 pm
ORD
-
CLO
18h 21m
1 stop
$362American Airlines
Thu, Mar 5 - Mon, Mar 9
Multiple Airlines Logo
6:57 am - 11:47 pm
CLO
-
ORD
17h 50m
2 stops
Multiple Airlines Logo
5:15 am - 2:15 pm
ORD
-
CLO
8h 00m
1 stop
$368Multiple Airlines
Wed, Feb 4 - Mon, Feb 9
Delta Logo
5:17 am - 11:57 pm
CLO
-
ORD
18h 40m
2 stops
Delta Logo
7:10 am - 12:45 am
ORD
-
CLO
17h 35m
2 stops
$375Delta
Wed, Jul 8 - Mon, Jul 13
Multiple Airlines Logo
3:22 pm - 11:22 am
CLO
-
ORD
21h 00m
1 stop
Multiple Airlines Logo
12:06 pm - 2:15 pm
ORD
-
CLO
25h 09m
1 stop
$377Multiple Airlines
Tue, Feb 17 - Sat, Feb 28
Avianca Logo
4:24 am - 1:15 pm
CLO
-
ORD
8h 51m
1 stop
Avianca Logo
2:35 pm - 11:33 pm
ORD
-
CLO
8h 58m
1 stop
$379Avianca
Thu, May 14 - Mon, May 25
LATAM Airlines Logo
12:35 pm - 10:14 am
CLO
-
ORD
22h 39m
2 stops
LATAM Airlines Logo
5:25 am - 9:00 pm
ORD
-
CLO
14h 35m
2 stops
$382LATAM Airlines
Wed, Feb 11 - Wed, Feb 18
Copa Airlines Logo
12:03 pm - 12:04 am
CLO
-
ORD
13h 01m
1 stop
Copa Airlines Logo
7:34 am - 11:36 pm
ORD
-
CLO
15h 02m
1 stop
$383Copa Airlines
Wed, Feb 11 - Wed, Feb 18

American Airlines flights from Cali to Chicago

Our best American Airlines deals on Cali to Chicago flight tickets
American Airlines
Mar 5
CLO3:20 pmCali Alfonso B. Aragon Intl
10h 17m
1 stop
ORD12:37 amChicago O'Hare Intl
Mar 9
ORD6:59 pmChicago O'Hare Intl
18h 21m
1 stop
CLO1:20 pmCali Alfonso B. Aragon Intl
$358
American Airlines
Mar 5
CLO3:20 pmCali Alfonso B. Aragon Intl
17h 04m
2 stops
ORD7:24 amChicago O'Hare Intl
Mar 9
ORD6:59 pmChicago O'Hare Intl
18h 21m
1 stop
CLO1:20 pmCali Alfonso B. Aragon Intl
$362

Spirit Airlines flights from Cali to Chicago

Our best Spirit Airlines deals on Cali to Chicago flight tickets
Spirit Airlines
Feb 4
CLO3:22 pmCali Alfonso B. Aragon Intl
9h 25m
1 stop
ORD11:47 pmChicago O'Hare Intl
Feb 7
ORD5:15 amChicago O'Hare Intl
8h 00m
1 stop
CLO2:15 pmCali Alfonso B. Aragon Intl
$293
Spirit Airlines
Feb 4
CLO3:22 pmCali Alfonso B. Aragon Intl
9h 25m
1 stop
ORD11:47 pmChicago O'Hare Intl
Feb 9
ORD5:15 amChicago O'Hare Intl
8h 00m
1 stop
CLO2:15 pmCali Alfonso B. Aragon Intl
$301
Spirit Airlines
Feb 4
CLO3:22 pmCali Alfonso B. Aragon Intl
23h 55m
2 stops
ORD2:17 pmChicago O'Hare Intl
Feb 7
ORD5:15 amChicago O'Hare Intl
8h 00m
1 stop
CLO2:15 pmCali Alfonso B. Aragon Intl
$311

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 January 21, 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

CaliChicago

CLO - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Wed 2/4

3:22 pm-11:47 pm

1 stop9h 25m

Chicago O'Hare Intl

Mon 2/9

5:15 am-2:15 pm

1 stop8h 00m

$301

CaliChicago

CLO - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Wed 2/4

3:22 pm-6:16 pm

3 stops27h 54m

Chicago O'Hare Intl

Mon 2/9

5:15 am-2:15 pm

1 stop8h 00m

$350

CaliChicago

CLO - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Thu 3/5

3:20 pm-12:37 am

1 stop10h 17m

Chicago O'Hare Intl

Mon 3/9

6:59 pm-1:20 pm

1 stop18h 21m

$358

CaliChicago

CLO - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Thu 3/5

3:20 pm-7:24 am

2 stops17h 04m

Chicago O'Hare Intl

Mon 3/9

6:59 pm-1:20 pm

1 stop18h 21m

$362

CaliChicago

CLO - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Wed 2/4

6:57 am-11:47 pm

2 stops17h 50m

Chicago O'Hare Intl

Mon 2/9

5:15 am-2:15 pm

1 stop8h 00m

$368

CaliChicago

CLO - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Wed 7/8

5:17 am-11:57 pm

2 stops18h 40m

Chicago O'Hare Intl

Mon 7/13

7:10 am-12:45 am

2 stops17h 35m

$375

CaliChicago

CLO - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Tue 2/17

3:22 pm-11:22 am

1 stop21h 00m

Chicago O'Hare Intl

Sat 2/28

12:06 pm-2:15 pm

1 stop25h 09m

$377

CaliChicago

CLO - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Thu 5/14

4:24 am-1:15 pm

1 stop8h 51m

Chicago O'Hare Intl

Mon 5/25

2:35 pm-11:33 pm

1 stop8h 58m

$379

CaliChicago

CLO - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Wed 2/11

12:35 pm-10:14 am

2 stops22h 39m

Chicago O'Hare Intl

Wed 2/18

5:25 am-9:00 pm

2 stops14h 35m

$382

CaliChicago

CLO - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Wed 2/11

12:03 pm-12:04 am

1 stop13h 01m

Chicago O'Hare Intl

Wed 2/18

7:34 am-11:36 pm

1 stop15h 02m

$383

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 $418.

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 $470 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 January 2026, prices for Cali to Chicago flights are approximately 11% 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 51m

Direct flights

None
The fastest flight from Cali to Chicago takes 8h 51m
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 51m 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
2,496 reviews
Search Avianca flights
American AirlinesPriceFrom $403Free CancellationRating
7.2
11,169 reviews
Search American Airlines flights
Copa AirlinesPriceFrom $414Free CancellationRating
7.6
1,559 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
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