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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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CLO
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Cali Alfonso B. Aragon Intl are usually found in September or August, booked 18 days in advance, depart on a Wednesday or Tuesday and return on a Wednesday

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 September 16, 2025.

Round-trip from

$280
(FlightHub)

One-way from

$150
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$244
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. 17% potential increase in price ($99 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($32 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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 September 16, 2025.

This FlightHub deal was found by Cheapflights users on 9/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/3011:20 pmORD - CLO
1 stop10h 50mAvianca
Mon 11/178:40 amCLO - ORD
1 stop12h 40mAvianca
Deal found 9/16$280
This Copa Airlines deal was found by Cheapflights users on 9/14. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/297:59 amORD - CLO
1 stop15h 36mCopa Airlines
Wed 11/512:04 pmCLO - ORD
1 stop13h 01mCopa Airlines
Deal found 9/14$285
This Spirit Airlines deal was found by Cheapflights users on 9/14. 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 Spirit Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/105:05 amORD - CLO
1 stop8h 10mSpirit Airlines
Thu 11/133:21 pmCLO - ORD
1 stop19h 02mSpirit Airlines
Deal found 9/14$287
This Copa Airlines deal was found by Cheapflights users on 9/15. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/307:59 amORD - CLO
1 stop9h 30mCopa Airlines
Mon 11/1712:04 pmCLO - ORD
1 stop13h 01mCopa Airlines
Deal found 9/15$289
This American Airlines deal was found by Cheapflights users on 9/14. 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.
Thu 10/308:44 pmORD - CLO
2 stops16h 36mAmerican Airlines
Mon 11/173:20 pmCLO - ORD
1 stop18h 45mAmerican Airlines
Deal found 9/14$298
This Expedia deal was found by Cheapflights users on 9/15. 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.
Mon 10/65:05 amORD - CLO
1 stop8h 18mSpirit Airlines
Thu 10/302:20 pmCLO - ORD
1 stop10h 43mSpirit Airlines
Deal found 9/15$311
This Copa Airlines deal was found by Cheapflights users on 9/14. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/106:56 amORD - CLO
1 stop27h 05mCopa Airlines
Wed 11/124:52 amCLO - ORD
1 stop8h 54mCopa Airlines
Deal found 9/14$330
This FlightHub deal was found by Cheapflights users on 9/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/242:35 pmORD - CLO
1 stop8h 43mAvianca
Mon 10/2711:50 amCLO - ORD
1 stop9h 30mAvianca
Deal found 9/16$333
This Cheapflightsfares deal was found by Cheapflights users on 9/16. 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.
Sun 10/57:43 pmORD - CLO
1 stop17h 40mSpirit Airlines
Fri 10/102:20 pmCLO - ORD
2 stops19h 54mSpirit Airlines
Deal found 9/16$341
This Cheapflightsfares deal was found by Cheapflights users on 9/16. 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.
Tue 10/145:05 amORD - CLO
1 stop8h 18mSpirit Airlines
Fri 10/172:20 pmCLO - ORD
1 stop9h 25mSpirit Airlines
Deal found 9/16$346

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 September 16, 2025.
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

Wed 10/29

7:59 am-11:35 pm

1 stop15h 36m

Cali Alfonso B. Aragon Intl

Wed 11/5

12:04 pm-12:05 am

1 stop13h 01m

$285

ChicagoCali

ORD - CLO

ORDCLO

Chicago O'Hare Intl

Mon 11/10

5:05 am-2:15 pm

1 stop8h 10m

Cali Alfonso B. Aragon Intl

Thu 11/13

3:21 pm-9:23 am

1 stop19h 02m

$287

ChicagoCali

ORD - CLO

ORDCLO

Chicago O'Hare Intl

Thu 10/30

7:59 am-5:29 pm

1 stop9h 30m

Cali Alfonso B. Aragon Intl

Mon 11/17

3:12 pm-12:05 am

1 stop9h 53m

$289

ChicagoCali

ORD - CLO

ORDCLO

Chicago O'Hare Intl

Thu 10/30

8:44 pm-1:20 pm

2 stops16h 36m

Cali Alfonso B. Aragon Intl

Mon 11/17

3:20 pm-9:05 am

1 stop18h 45m

$298

ChicagoCali

ORD - CLO

ORDCLO

Chicago O'Hare Intl

Mon 11/10

6:46 am-9:46 pm

2 stops14h 00m

Cali Alfonso B. Aragon Intl

Thu 11/13

3:20 pm-9:05 am

1 stop18h 45m

$298

ChicagoCali

ORD - CLO

ORDCLO

Chicago O'Hare Intl

Wed 11/12

6:46 am-9:46 pm

2 stops14h 00m

Cali Alfonso B. Aragon Intl

Mon 11/17

7:00 am-12:37 am

1 stop18h 37m

$298

ChicagoCali

ORD - CLO

ORDCLO

Chicago O'Hare Intl

Sat 11/15

5:05 am-7:14 am

2 stops25h 09m

$150

ChicagoCali

ORD - CLO

ORDCLO

Chicago O'Hare Intl

Sat 11/15

5:05 am-2:15 pm

1 stop8h 10m

$155

ChicagoCali

ORD - CLO

ORDCLO

Chicago O'Hare Intl

Tue 10/14

6:18 pm-1:23 pm

2 stops19h 05m

$205

ChicagoCali

ORD - CLO

ORDCLO

Chicago O'Hare Intl

Mon 12/1

10:20 pm-10:10 am

1 stop10h 50m

$218

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 13 results
1
2

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 September 12, 2025.

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, January is the cheapest month in which you can book a flight from Chicago to Cali (average of $351). Flying from Chicago to Cali in December is currently the most expensive (average of $669). 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 is the cheapest time of day to fly from CHI to CLO?

Find hourly flight availability from Chicago to Cali. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 16, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago to Cali in the morning. If you’re flexible enough to do this you can expect to save up to 12% on your trip compared to booking a flight in the afternoon.

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 69% 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 $384.

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 Bogotá (BOG) have the shortest average one-way travel time for 1-stop routes: 9h 09m.

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 September 16, 2025.
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
1,531 reviews

Food

6.8

Comfort

7.4

Entertainment

6.8

Overall

7.6

Boarding

7.8

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Juan Pablo,Sep 2025

MEX - PTY

never better, had a very plesent trip to panama, cant say the same thing of my trip, from panama to santa cruz... it was very poor, unconftrable and boring
Copa Airlines
7.6
Good
1,531 reviews
Copa Airlines
7.6
Good
1,531 reviews

Food

6.8

Comfort

7.4

Entertainment

6.8

Overall

7.6

Boarding

7.8

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Juan Pablo,Sep 2025

MEX - PTY

never better, had a very plesent trip to panama, cant say the same thing of my trip, from panama to santa cruz... it was very poor, unconftrable and boring
American Airlines
7.2
Good
10,000 reviews
Copa Airlines
7.6
Good
1,531 reviews

Food

6.8

Comfort

7.4

Entertainment

6.8

Overall

7.6

Boarding

7.8

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Juan Pablo,Sep 2025

MEX - PTY

never better, had a very plesent trip to panama, cant say the same thing of my trip, from panama to santa cruz... it was very poor, unconftrable and boring
Avianca
6.7
Okay
2,435 reviews
Copa Airlines
7.6
Good
1,531 reviews

Food

6.8

Comfort

7.4

Entertainment

6.8

Overall

7.6

Boarding

7.8

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Juan Pablo,Sep 2025

MEX - PTY

never better, had a very plesent trip to panama, cant say the same thing of my trip, from panama to santa cruz... it was very poor, unconftrable and boring
Spirit Airlines
6.3
Okay
8,019 reviews
Copa Airlines
7.6
Good
1,531 reviews

Food

6.8

Comfort

7.4

Entertainment

6.8

Overall

7.6

Boarding

7.8

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Juan Pablo,Sep 2025

MEX - PTY

never better, had a very plesent trip to panama, cant say the same thing of my trip, from panama to santa cruz... it was very poor, unconftrable and boring

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 8h 10m. Fly via Copa Airlines or Spirit Airlines to get the fastest option. There are 2748 mi between Chicago and Cali. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 $319 on this airline. Additional options worth looking into are Avianca and Copa Airlines, starting at $330 and $368 round-trip. Spirit Airlines is currently priced 30% 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, January is the cheapest month in which you can book a flight from Chicago to Cali (average of $351). Flying from Chicago to Cali in December is currently the most expensive (average of $669). 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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$319Average$541FlexibilityNo cancel feeOn-time65%
AviancaCheapest$330Average$518FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$368Average$463FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$406Average$620FlexibilityNo cancel feeOn-time71%
LATAM AirlinesCheapest$624Average$739FlexibilityNo cancel feeOn-time81%

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