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Cheap flights from Cali to Chicago from $208

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 10/25. 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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Find the cheapest flights from Cali to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Spirit Airlines Logo
3:25 pm - 2:51 pmCLO-ORD
24h 26m2 stops
Spirit Airlines Logo
5:10 am - 2:08 pmORD-CLO
7h 58m1 stop
$331Spirit Airlines
Find Deal
Tue, Nov 11 - Tue, Nov 18
Spirit Airlines Logo
3:25 pm - 11:13 pmCLO-ORD
8h 48m1 stop
Spirit Airlines Logo
5:00 am - 2:30 pmORD-CLO
8h 30m1 stop
$332Spirit Airlines
Find Deal
Thu, Nov 20 - Sun, Nov 23
Delta Logo
5:07 am - 9:14 pmCLO-ORD
17h 07m2 stops
Delta Logo
5:50 am - 7:15 pmORD-CLO
12h 25m2 stops
$337Delta
Find Deal
Fri, Feb 13 - Tue, Feb 17
LATAM Airlines Logo
8:07 am - 8:32 amCLO-ORD
24h 25m2 stops
LATAM Airlines Logo
9:51 am - 7:21 amORD-CLO
20h 30m2 stops
$346LATAM Airlines
Find Deal
Wed, Oct 29 - Wed, Nov 12
Spirit Airlines Logo
3:25 pm - 12:27 amCLO-ORD
10h 02m1 stop
Spirit Airlines Logo
5:10 am - 2:08 pmORD-CLO
7h 58m1 stop
$347Spirit Airlines
Find Deal
Tue, Nov 11 - Tue, Nov 18
LATAM Airlines Logo
8:07 am - 8:32 amCLO-ORD
24h 25m2 stops
LATAM Airlines Logo
9:51 am - 8:31 amORD-CLO
21h 40m2 stops
$348LATAM Airlines
Find Deal
Wed, Oct 29 - Wed, Nov 12
Avianca Logo
11:55 am - 9:20 pmCLO-ORD
9h 25m1 stop
Avianca Logo
10:20 pm - 11:55 amORD-CLO
12h 35m1 stop
$395Avianca
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Sun, Oct 26 - Tue, Nov 11
Copa Airlines Logo
8:48 am - 12:56 amCLO-ORD
16h 08m1 stop
Copa Airlines Logo
6:56 am - 11:37 pmORD-CLO
15h 41m1 stop
$404Copa Airlines
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Wed, Oct 29 - Wed, Nov 12
Avianca Logo
10:15 am - 8:20 pmCLO-ORD
11h 05m1 stop
Avianca Logo
10:20 pm - 11:55 amORD-CLO
12h 35m1 stop
$406Avianca
Find Deal
Wed, Feb 11 - Wed, Feb 18
Copa Airlines Logo
6:37 pm - 12:52 pmCLO-ORD
19h 15m1 stop
Copa Airlines Logo
7:35 am - 11:34 pmORD-CLO
14h 59m1 stop
$494Copa Airlines
Find Deal
Fri, Dec 26 - Mon, Jan 19

Spirit Airlines flights from Cali to Chicago

Our best Spirit Airlines deals on Cali to Chicago flight tickets
Spirit Airlines
Nov 11
CLO3:25 pmCali Alfonso B. Aragon Intl
24h 26m
2 stops
ORD2:51 pmChicago O'Hare Intl
Nov 18
ORD5:10 amChicago O'Hare Intl
7h 58m
1 stop
CLO2:08 pmCali Alfonso B. Aragon Intl
$331
Find similar
Spirit Airlines
Nov 20
CLO3:25 pmCali Alfonso B. Aragon Intl
8h 48m
1 stop
ORD11:13 pmChicago O'Hare Intl
Nov 23
ORD5:00 amChicago O'Hare Intl
8h 30m
1 stop
CLO2:30 pmCali Alfonso B. Aragon Intl
$332
Find similar
Spirit Airlines
Nov 11
CLO3:25 pmCali Alfonso B. Aragon Intl
10h 02m
1 stop
ORD12:27 amChicago O'Hare Intl
Nov 18
ORD5:10 amChicago O'Hare Intl
7h 58m
1 stop
CLO2:08 pmCali Alfonso B. Aragon Intl
$347
Find similar

LATAM Airlines flights from Cali to Chicago

Our best LATAM Airlines deals on Cali to Chicago flight tickets
LATAM Airlines
Oct 29
CLO8:07 amCali Alfonso B. Aragon Intl
24h 25m
2 stops
ORD8:32 amChicago O'Hare Intl
Nov 12
ORD9:51 amChicago O'Hare Intl
20h 30m
2 stops
CLO7:21 amCali Alfonso B. Aragon Intl
$346
Find similar
LATAM Airlines
Oct 29
CLO8:07 amCali Alfonso B. Aragon Intl
24h 25m
2 stops
ORD8:32 amChicago O'Hare Intl
Nov 12
ORD9:51 amChicago O'Hare Intl
21h 40m
2 stops
CLO8:31 amCali Alfonso B. Aragon Intl
$348
Find similar
LATAM Airlines
Feb 11
CLO10:45 pmCali Alfonso B. Aragon Intl
18h 54m
2 stops
ORD4:39 pmChicago O'Hare Intl
Feb 18
ORD7:10 amChicago O'Hare Intl
14h 55m
2 stops
CLO11:05 pmCali Alfonso B. Aragon Intl
$350
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 October 14, 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

Tue 11/11

3:25 pm-2:51 pm

2 stops24h 26m

Chicago O'Hare Intl

Tue 11/18

5:10 am-2:08 pm

1 stop7h 58m

$331

CaliChicago

CLO - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Thu 11/20

3:25 pm-11:13 pm

1 stop8h 48m

Chicago O'Hare Intl

Sun 11/23

5:00 am-2:30 pm

1 stop8h 30m

$332

CaliChicago

CLO - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Fri 2/13

5:07 am-9:14 pm

2 stops17h 07m

Chicago O'Hare Intl

Tue 2/17

5:50 am-7:15 pm

2 stops12h 25m

$337

CaliChicago

CLO - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Wed 10/29

8:07 am-8:32 am

2 stops24h 25m

Chicago O'Hare Intl

Wed 11/12

9:51 am-7:21 am

2 stops20h 30m

$346

CaliChicago

CLO - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Tue 11/11

3:25 pm-12:27 am

1 stop10h 02m

Chicago O'Hare Intl

Tue 11/18

5:10 am-2:08 pm

1 stop7h 58m

$347

CaliChicago

CLO - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Wed 10/29

8:07 am-8:32 am

2 stops24h 25m

Chicago O'Hare Intl

Wed 11/12

9:51 am-8:31 am

2 stops21h 40m

$348

CaliChicago

CLO - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Sun 10/26

11:55 am-9:20 pm

1 stop9h 25m

Chicago O'Hare Intl

Tue 11/11

10:20 pm-11:55 am

1 stop12h 35m

$395

CaliChicago

CLO - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Wed 10/29

8:48 am-12:56 am

1 stop16h 08m

Chicago O'Hare Intl

Wed 11/12

6:56 am-11:37 pm

1 stop15h 41m

$404

CaliChicago

CLO - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Wed 2/11

10:15 am-8:20 pm

1 stop11h 05m

Chicago O'Hare Intl

Wed 2/18

10:20 pm-11:55 am

1 stop12h 35m

$406

CaliChicago

CLO - ORD

CLOORD

Cali Alfonso B. Aragon Intl

Fri 12/26

6:37 pm-12:52 pm

1 stop19h 15m

Chicago O'Hare Intl

Mon 1/19

7:35 am-11:34 pm

1 stop14h 59m

$494

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 November is, on average, the cheapest month to fly to Chicago from Cali, with most prices found around $404. If you’re not able to fly to Chicago in November, then September is your next best option. Flight prices from Cali to Chicago during September average around $412.

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 $454 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 October 2025, prices for Cali to Chicago flights are approximately 24% 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

Direct flights

None
There are no direct flights from Cali to Chicago. There are no popular flight routes from Cali to Chicago.
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  • 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 40m 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
2,451 reviews
Search Avianca flights
Copa AirlinesPriceFrom $378Free CancellationRating
7.6
1,547 reviews
Search Copa Airlines flights
American AirlinesPriceFrom $403Free CancellationRating
7.2
11,043 reviews
Search American 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