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$150+ Cheap flights from Chicago (CHI) to Cali (CLO)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/22. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CLO
Feb 7 — Feb 141
Sat 2/7
Sat 2/14
1 adult, Economy
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Cheap flight deals from Chicago to Cali

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Cali (CLO). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 8, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$254
(Cheapflightsfares)

One-way from

$141
(FlightHub)

Popular in

December

Cheapest in

September

Average price

$445
Provider with most accurate pricing for Chicago (CHI)-Cali Alfonso B. Aragon Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Cali Alfonso B. Aragon Intl flights.
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From Chicago (CHI) to Cali Alfonso B. Aragon Intl
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One-way flight from Chicago (CHI) to Cali Alfonso B. Aragon Intl
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Highest demand for flights based on searches. 21% potential increase in price ($127 potential increase over avg. RT price).
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Cheapest flight prices on average. 9% potential price decrease ($41 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Find flight deals from Chicago to Cali

Cheapest flights from Chicago to Cali
Explore the most affordable flight options available from Chicago to Cali. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 8, 2026.

This Cheapflightsfares deal was found by Cheapflights users on 1/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/75:32 pmORD - CLO
1 stop19h 43mSpirit Airlines
Sat 2/283:22 pmCLO - ORD
1 stop9h 25mSpirit Airlines
Deal found 1/7$254
This Kiwi.com deal was found by Cheapflights users on 1/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/2112:06 pmORD - CLO
1 stop25h 09mMultiple Airlines
Sat 2/283:22 pmCLO - ORD
1 stop9h 25mMultiple Airlines
Deal found 1/7$276
This Expedia deal was found by Cheapflights users on 1/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/218:59 amORD - CLO
2 stops28h 16mSpirit Airlines
Sat 2/283:22 pmCLO - ORD
1 stop9h 25mSpirit Airlines
Deal found 1/7$281
This Cheapflightsfares deal was found by Cheapflights users on 1/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/285:15 amORD - CLO
1 stop8h 00mSpirit Airlines
Fri 2/63:22 pmCLO - ORD
1 stop9h 25mSpirit Airlines
Deal found 1/8$292
This Mytrip deal was found by Cheapflights users on 1/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/510:20 pmORD - CLO
1 stop10h 10mAvianca
Fri 3/1311:50 amCLO - ORD
1 stop9h 30mAvianca
Deal found 1/7$331
This Avianca deal was found by Cheapflights users on 1/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/2210:20 pmORD - CLO
1 stop11h 45mAvianca
Mon 1/268:40 amCLO - ORD
1 stop12h 40mAvianca
Deal found 1/6$332
This Cheapflightsfares deal was found by Cheapflights users on 1/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/115:15 amORD - CLO
1 stop8h 00mSpirit Airlines
Wed 2/183:22 pmCLO - ORD
2 stops17h 32mSpirit Airlines
Deal found 1/7$333
This Orbitz deal was found by Cheapflights users on 1/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/18:43 pmORD - CLO
1 stop16h 32mSpirit Airlines
Sun 2/83:22 pmCLO - ORD
2 stops23h 55mSpirit Airlines
Deal found 1/7$341
This American Airlines deal was found by Cheapflights users on 1/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/108:58 pmORD - CLO
2 stops16h 22mAmerican Airlines
Tue 3/172:20 pmCLO - ORD
2 stops17h 05mAmerican Airlines
Deal found 1/5$345

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Cali 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, Cheapflights users made 2,558,603 searches. Data last updated January 8, 2026.
Use the filters below to find and compare flights from Chicago to Cali that are best for you.

Fly from

Chicago

Fly to

Cali

Route

Depart

Return

Price

ChicagoCali

ORD - CLO

ORDCLO

Chicago O'Hare Intl

Sun 2/8

8:43 pm-2:15 pm

1 stop16h 32m

Cali Alfonso B. Aragon Intl

Thu 2/26

3:22 pm-11:47 pm

1 stop9h 25m

$257

ChicagoCali

ORD - CLO

ORDCLO

Chicago O'Hare Intl

Mon 2/2

5:15 am-2:15 pm

1 stop8h 00m

Cali Alfonso B. Aragon Intl

Wed 2/25

3:22 pm-7:54 am

2 stops17h 32m

$271

ChicagoCali

ORD - CLO

ORDCLO

Chicago O'Hare Intl

Sat 2/21

12:06 pm-2:15 pm

1 stop25h 09m

Cali Alfonso B. Aragon Intl

Sat 2/28

3:22 pm-11:47 pm

1 stop9h 25m

$276

ChicagoCali

ORD - CLO

ORDCLO

Chicago O'Hare Intl

Wed 1/28

5:15 am-2:15 pm

1 stop8h 00m

Cali Alfonso B. Aragon Intl

Fri 2/6

3:22 pm-11:47 pm

1 stop9h 25m

$292

ChicagoCali

ORD - CLO

ORDCLO

Chicago O'Hare Intl

Sat 2/21

8:59 am-2:15 pm

2 stops28h 16m

Cali Alfonso B. Aragon Intl

Sat 2/28

3:22 pm-7:54 am

2 stops17h 32m

$311

ChicagoCali

ORD - CLO

ORDCLO

Chicago O'Hare Intl

Sat 1/31

10:20 pm-9:05 am

1 stop9h 45m

Cali Alfonso B. Aragon Intl

Sun 2/8

10:55 am-8:20 pm

1 stop10h 25m

$332

ChicagoCali

ORD - CLO

ORDCLO

Chicago O'Hare Intl

Thu 4/9

2:35 pm-11:18 pm

1 stop8h 43m

Cali Alfonso B. Aragon Intl

Sun 4/12

8:27 pm-1:15 pm

1 stop16h 48m

$332

ChicagoCali

ORD - CLO

ORDCLO

Chicago O'Hare Intl

Wed 2/11

5:15 am-2:15 pm

1 stop8h 00m

Cali Alfonso B. Aragon Intl

Wed 2/18

3:22 pm-7:54 am

2 stops17h 32m

$333

ChicagoCali

ORD - CLO

ORDCLO

Chicago O'Hare Intl

Sun 2/1

8:43 pm-2:15 pm

1 stop16h 32m

Cali Alfonso B. Aragon Intl

Sun 2/8

3:22 pm-2:17 pm

2 stops23h 55m

$341

ChicagoCali

ORD - CLO

ORDCLO

Chicago O'Hare Intl

Sat 1/31

12:00 pm-2:15 pm

1 stop25h 15m

Cali Alfonso B. Aragon Intl

Sun 2/8

3:22 pm-6:29 pm

2 stops28h 07m

$345

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/7

Showing 1-10 of 18 results
1
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Compare providers for flights from Chicago to Cali

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Cali in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
AranGrantPrice Accuracy2 starsTrust Score*3 stars
OvagoPrice Accuracy2 starsTrust Score*2 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Cali flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-Cali flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago-Cali flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Cali flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Cali flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to Cali

Have a flexible travel schedule? Discover the best time to fly to Cali from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Cali

How far ahead should I book a flight from Chicago to Cali?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Cali. Price data was last updated on January 2, 2026.

The price you pay for your flight from Chicago to Cali may vary depending on when you book. For the best chance of a lower fare, look to book 18 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Chicago to Cali?

Currently, September is the cheapest month in which you can book a flight from Chicago to Cali (average of $183). Flying from Chicago to Cali in August is currently the most expensive (average of $376). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What’s the top layover airport for flights from Chicago to Cali?

Share of 1-stop round-trip flights from Chicago to Cali chosen by Cheapflights users in the past 12 months, using the same layover each way.

Panama City (PTY) – chosen by Cheapflights users on 74% of 1-stop itineraries from Chicago to Cali on Cheapflights.

What’s the cheapest layover airport for flights from Chicago to Cali?

Average round-trip fare for 1-stop flights from Chicago to Cali, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Bogotá (BOG) is the most affordable 1-stop option, with an average round-trip price of $411.

What’s the fastest layover option from Chicago to Cali?

Shortest average travel time for 1-stop one-way flights from Chicago to Cali, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Panama City (PTY) have the shortest average one-way travel time for 1-stop routes: 9h 02m.

Which airport typically offers the quickest layover for flights from Chicago to Cali?

Average layover duration for 1-stop one-way flights from Chicago to Cali, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Bogotá (BOG) offer the fastest connection on this route, with an average layover time of 1h 51m.

Reviews of airlines servicing Cali

Get insights into the airlines that provide service to Cali. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Cali. Reviews last updated January 8, 2026.
Read reviews from past customers who have flown Copa Airlines, American Airlines, and Avianca from Chicago to Cali. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Copa Airlines
7.6
Good
1,562 reviews

Crew

8.1

Comfort

7.4

Boarding

7.8

Food

6.8

Overall

7.6

Entertainment

6.8

Reviews

1 / 20
2.0
Mediocre

Juan,Dec 2025

EZE - PTY

The outbound flight from Boston was awful. The handicapped services were the worst i have ever seen. NEVER AGAIN. THIS WAS NOT WORTH ANYWHERE NEAR $4K.
Copa Airlines
7.6
Good
1,562 reviews
Copa Airlines
7.6
Good
1,562 reviews

Crew

8.1

Comfort

7.4

Boarding

7.8

Food

6.8

Overall

7.6

Entertainment

6.8

Reviews

1 / 20
2.0
Mediocre

Juan,Dec 2025

EZE - PTY

The outbound flight from Boston was awful. The handicapped services were the worst i have ever seen. NEVER AGAIN. THIS WAS NOT WORTH ANYWHERE NEAR $4K.
American Airlines
7.2
Good
11,095 reviews
Copa Airlines
7.6
Good
1,562 reviews

Crew

8.1

Comfort

7.4

Boarding

7.8

Food

6.8

Overall

7.6

Entertainment

6.8

Reviews

1 / 20
2.0
Mediocre

Juan,Dec 2025

EZE - PTY

The outbound flight from Boston was awful. The handicapped services were the worst i have ever seen. NEVER AGAIN. THIS WAS NOT WORTH ANYWHERE NEAR $4K.
Avianca
6.6
Okay
2,494 reviews
Copa Airlines
7.6
Good
1,562 reviews

Crew

8.1

Comfort

7.4

Boarding

7.8

Food

6.8

Overall

7.6

Entertainment

6.8

Reviews

1 / 20
2.0
Mediocre

Juan,Dec 2025

EZE - PTY

The outbound flight from Boston was awful. The handicapped services were the worst i have ever seen. NEVER AGAIN. THIS WAS NOT WORTH ANYWHERE NEAR $4K.
Spirit Airlines
6.3
Okay
8,287 reviews
Copa Airlines
7.6
Good
1,562 reviews

Crew

8.1

Comfort

7.4

Boarding

7.8

Food

6.8

Overall

7.6

Entertainment

6.8

Reviews

1 / 20
2.0
Mediocre

Juan,Dec 2025

EZE - PTY

The outbound flight from Boston was awful. The handicapped services were the worst i have ever seen. NEVER AGAIN. THIS WAS NOT WORTH ANYWHERE NEAR $4K.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Cali. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Cali from Chicago?

    Located just 12.1 mi from the city center, Cali Alfonso B. Aragon Intl is the airport most travelers will use when flying to Cali from Chicago. Booking flights from Chicago to Alfonso B. Aragon Intl (CLO) should be relatively easy as there are 0 daily inbound flights from Chicago from 5 different airlines.

  • How long is the flight from Chicago to Cali?

    There are many flights that can get you from Chicago to Cali in 19h 43m. Fly via Spirit Airlines to get the fastest option. There are 2748 mi between Chicago and Cali.

  • What are the cheapest airlines flying from Chicago to Cali round-trip?

    Our cheapest airline available from Chicago to Cali is Spirit Airlines. Our recent data shows that you can find tickets from as low as $120 on this airline. Additional options worth looking into are Avianca and American Airlines, starting at $180 and $295 round-trip. Spirit Airlines is currently priced 73% below the average price you’ll pay for this route.

  • Can I find deals for flights from Chicago to Cali that include hotel bookings?

    Yes. In addition to deals on Chicago to Cali flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Cali?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Cali.

  • Can I find deals for business class flights from Chicago to Cali?

    Yes. Cheapflights offers flight deals from Chicago to Cali by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Cali?

    Currently, September is the cheapest month in which you can book a flight from Chicago to Cali (average of $183). Flying from Chicago to Cali in August is currently the most expensive (average of $376). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Chicago to Cali

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Chicago to Cali

Discover the top 5 airlines that operate flights from Chicago to Cali. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$126Average$613FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$295Average$620FlexibilityNo cancel feeOn-time71%
AviancaCheapest$330Average$541FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$341Average$459FlexibilityNo cancel feeOn-time70%
LATAM AirlinesCheapest$624Average$739FlexibilityNo cancel feeOn-time81%

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