$190+ 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 11/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CLO
Oct 1 — Oct 81
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Cali with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to Cali
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Best
Last-minute
One-way
Cheapest flights from Chicago to CaliExplore 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 1, 2026.
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 1, 2026.
This United Airlines deal was found by Cheapflights users on 8/31. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/59:35 pm -
2 stops18h 57m
Thu 11/1212:05 pm -
2 stops13h 40m
Deal found 8/31![United Airlines logo]()
$431
This Delta deal was found by Cheapflights users on 8/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/45:27 am -
2 stops16h 18m
Wed 11/115:20 am -
2 stops19h 34m
Deal found 8/31![Delta logo]()
$436
This United Airlines deal was found by Cheapflights users on 9/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/155:45 pm -
2 stops29h 48m
Sat 10/2412:06 pm -
2 stops21h 04m
Deal found 9/1![United Airlines logo]()
$438
This Delta deal was found by Cheapflights users on 8/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/35:05 pm -
2 stops28h 40m
Mon 11/912:15 pm -
2 stops22h 07m
Deal found 8/31![Delta logo]()
$443
This LATAM Airlines deal was found by Cheapflights users on 8/31. 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 LATAM Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/85:27 am -
2 stops14h 48m
Thu 11/126:50 am -
2 stops26h 51m
Deal found 8/31![LATAM Airlines logo]()
$449
This United Airlines deal was found by Cheapflights users on 8/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/315:30 am -
2 stops12h 03m
Mon 9/2112:08 pm -
2 stops19h 47m
Deal found 8/28![United Airlines logo]()
$454
This LATAM Airlines deal was found by Cheapflights users on 8/31. 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 LATAM Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/76:08 pm -
2 stops26h 07m
Thu 11/126:50 am -
2 stops26h 51m
Deal found 8/31![LATAM Airlines logo]()
$456
This United deal was found by Cheapflights users on 9/1. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/912:40 pm -
2 stops16h 15m
Mon 11/1612:05 pm -
2 stops13h 40m
Deal found 9/1![Multiple Airlines logo]()
$461
This United Airlines deal was found by Cheapflights users on 8/31. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/75:30 am -
2 stops11h 02m
Tue 11/108:42 am -
2 stops17h 04m
Deal found 8/31![United Airlines logo]()
$464
This United Airlines deal was found by Cheapflights users on 8/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/306:30 am -
2 stops11h 03m
Sat 9/58:48 am -
2 stops16h 11m
Deal found 8/29![United Airlines logo]()
$467
This Copa Airlines deal was found by Cheapflights users on 8/28. 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.
Fri 10/233:20 pm -
1 stop22h 50m
Wed 10/2812:09 pm -
1 stop12h 56m
Deal found 8/28![Copa Airlines logo]()
$470
This United Airlines deal was found by Cheapflights users on 9/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/239:35 pm -
2 stops26h 02m
Wed 10/284:40 am -
2 stops20h 05m
Deal found 9/1![United Airlines logo]()
$472
Best flights from Chicago to CaliDiscover carefully curated flight deals from Chicago to Cali that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 1, 2026.
Discover carefully curated flight deals from Chicago to Cali that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 1, 2026.
This United Airlines deal was found by Cheapflights users on 8/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/65:30 am -
2 stops11h 02m
Wed 11/1112:05 pm -
2 stops23h 06m
Deal found 8/30![United Airlines logo]()
$431
This United deal was found by Cheapflights users on 9/1. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/912:40 pm -
2 stops16h 15m
Mon 11/1612:05 pm -
2 stops13h 40m
Deal found 9/1![Multiple Airlines logo]()
$461
This Copa Airlines deal was found by Cheapflights users on 8/28. 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.
Fri 10/233:20 pm -
1 stop22h 50m
Wed 10/2812:09 pm -
1 stop12h 56m
Deal found 8/28![Copa Airlines logo]()
$470
This United Airlines deal was found by Cheapflights users on 8/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:25 am -
2 stops17h 12m
Tue 10/278:46 am -
2 stops23h 05m
Deal found 8/29![United Airlines logo]()
$431
This United deal was found by Cheapflights users on 8/28. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/96:25 pm -
2 stops14h 35m
Mon 9/148:48 am -
2 stops16h 11m
Deal found 8/28![Multiple Airlines logo]()
$470
This Copa Airlines deal was found by Cheapflights users on 8/29. 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.
Tue 11/242:13 pm -
1 stop25h 51m
Wed 12/212:02 pm -
1 stop13h 09m
Deal found 8/29![Copa Airlines logo]()
$470
This United Airlines deal was found by Cheapflights users on 8/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/65:30 am -
2 stops11h 02m
Mon 11/94:38 am -
2 stops17h 52m
Deal found 8/30![United Airlines logo]()
$431
This Copa Airlines deal was found by Cheapflights users on 8/30. 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.
Fri 11/62:13 pm -
1 stop26h 19m
Mon 11/94:38 am -
1 stop20h 33m
Deal found 8/30![Copa Airlines logo]()
$470
This United Airlines deal was found by Cheapflights users on 8/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/159:35 pm -
2 stops26h 02m
Tue 10/2012:06 pm -
2 stops12h 17m
Deal found 8/30![United Airlines logo]()
$438
This United Airlines deal was found by Cheapflights users on 8/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/115:00 am -
2 stops18h 33m
Mon 9/148:48 am -
2 stops24h 21m
Deal found 8/28![United Airlines logo]()
$464
Last-minute flights from Chicago to CaliDiscover last-minute flight deals from Chicago to Cali. Data last updated September 1, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Cali. Data last updated September 1, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/29. 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.
Wed 9/28:01 am -
1 stop9h 32m
Thu 9/312:08 pm -
1 stop12h 54m
Deal found 8/29![Copa Airlines logo]()
$518
This United Airlines deal was found by Cheapflights users on 8/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/31:30 pm -
2 stops28h 03m
Thu 9/1012:08 pm -
2 stops21h 01m
Deal found 8/30![United Airlines logo]()
$467
This KAYAK deal was found by Cheapflights users on 8/31. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/47:15 am -
2 stops16h 18m
Sun 9/68:48 am -
2 stops16h 11m
Deal found 8/31![Copa Airlines logo]()
$521
This United Airlines deal was found by Cheapflights users on 8/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/115:00 am -
2 stops18h 33m
Mon 9/148:48 am -
2 stops24h 21m
Deal found 8/28![United Airlines logo]()
$464
This United Airlines deal was found by Cheapflights users on 8/31. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/149:35 pm -
2 stops25h 58m
Thu 9/1712:08 pm -
2 stops19h 47m
Deal found 8/31![United Airlines logo]()
$473
This Ovago deal was found by Cheapflights users on 9/1. 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 Ovago is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/149:35 pm -
2 stops25h 58m
Thu 9/1712:08 pm -
2 stops12h 51m
Deal found 9/1![Copa Airlines logo]()
$496
This United Airlines deal was found by Cheapflights users on 9/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/155:45 pm -
2 stops29h 48m
Sat 10/2412:06 pm -
2 stops21h 04m
Deal found 9/1![United Airlines logo]()
$438
This Copa Airlines deal was found by Cheapflights users on 9/1. 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 9/213:20 pm -
1 stop19h 48m
Sat 10/2412:06 pm -
1 stop12h 51m
Deal found 9/1![Copa Airlines logo]()
$490
This Copa Airlines deal was found by Cheapflights users on 8/28. 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.
Fri 10/233:20 pm -
1 stop22h 50m
Wed 10/2812:09 pm -
1 stop12h 56m
Deal found 8/28![Copa Airlines logo]()
$470
This United Airlines deal was found by Cheapflights users on 9/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/239:35 pm -
2 stops26h 02m
Wed 10/284:40 am -
2 stops20h 05m
Deal found 9/1![United Airlines logo]()
$472
This United Airlines deal was found by Cheapflights users on 8/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:25 am -
2 stops17h 12m
Tue 10/278:46 am -
2 stops23h 05m
Deal found 8/27![United Airlines logo]()
$431
One-way flights from Chicago to CaliSearch for one-way flight options from Chicago to Cali. Find affordable one-way fares based on user searches. Data last updated September 1, 2026.
Search for one-way flight options from Chicago to Cali. Find affordable one-way fares based on user searches. Data last updated September 1, 2026.
This United Airlines deal was found by Cheapflights users on 8/31. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/59:35 pm -
2 stops18h 57m
Deal found 8/31![United Airlines logo]()
$190
This United deal was found by Cheapflights users on 8/31. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/710:34 am -
2 stops18h 21m
Deal found 8/31![Multiple Airlines logo]()
$196
This United Airlines deal was found by Cheapflights users on 8/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/188:40 pm -
2 stops25h 52m
Deal found 8/28![United Airlines logo]()
$203
This Kiwi.com deal was found by Cheapflights users on 8/28. 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 9/512:44 am -
3 stops53h 33m
Deal found 8/28![Multiple Airlines logo]()
$213
This Viajes Falabella deal was found by Cheapflights users on 9/1. 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 Viajes Falabella is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/306:15 pm -
2 stops26h 00m
Deal found 9/1![LATAM Airlines logo]()
$216
This United Airlines deal was found by Cheapflights users on 8/31. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/195:55 am -
2 stops16h 37m
Deal found 8/31![United Airlines logo]()
$223
This United deal was found by Cheapflights users on 8/28. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:30 am -
2 stops15h 35m
Deal found 8/28![Multiple Airlines logo]()
$224
This United Airlines deal was found by Cheapflights users on 8/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/49:35 pm -
2 stops19h 58m
Deal found 8/29![United Airlines logo]()
$228
This United deal was found by Cheapflights users on 8/30. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/217:52 pm -
2 stops16h 08m
Deal found 8/30![Multiple Airlines logo]()
$229
This Kiwi.com deal was found by Cheapflights users on 8/30. 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.
Sun 9/205:30 am -
2 stops24h 35m
Deal found 8/30![LATAM Airlines logo]()
$237
This oojo deal was found by Cheapflights users on 8/28. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/183:26 pm -
1 stop26h 04m
Deal found 8/28![Aeromexico logo]()
$246
This Kiwi.com deal was found by Cheapflights users on 8/29. 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.
Fri 10/23:20 pm -
2 stops30h 13m
Deal found 8/29![Multiple Airlines logo]()
$248
Find 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 1, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $431 (United Airlines) |
One-way from | $190 (United Airlines) |
Popular in | December |
Cheapest in | February |
Average price | $446 |
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 7,457,451 searches. Data last updated September 1, 2026.
Use the filters below to find and compare flights from Chicago to Cali that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoCali
ORD Chicago O'Hare Intl - CLO Cali Alfonso B. Aragon Intl
ORDCLO
Chicago O'Hare Intl
Fri 11/6
5:30 am-5:32 pm
2 stops11h 02m
Cali Alfonso B. Aragon Intl
Wed 11/11
12:05 pm-10:11 am
2 stops23h 06m
$431
ChicagoCali
ORD Chicago O'Hare Intl - CLO Cali Alfonso B. Aragon Intl
ORDCLO
Chicago O'Hare Intl
Sat 10/24
6:25 am-11:37 pm
2 stops17h 12m
Cali Alfonso B. Aragon Intl
Tue 10/27
8:46 am-7:51 am
2 stops23h 05m
$431
Quickest round-trip
ChicagoCali
ORD Chicago O'Hare Intl - CLO Cali Alfonso B. Aragon Intl
ORDCLO
Chicago O'Hare Intl
Fri 11/6
5:30 am-5:32 pm
2 stops11h 02m
Cali Alfonso B. Aragon Intl
Mon 11/9
4:38 am-9:30 pm
2 stops17h 52m
$431
ChicagoCali
ORD Chicago O'Hare Intl - CLO Cali Alfonso B. Aragon Intl
ORDCLO
Chicago O'Hare Intl
Thu 10/15
9:35 pm-11:37 pm
2 stops26h 02m
Cali Alfonso B. Aragon Intl
Tue 10/20
12:06 pm-12:23 am
2 stops12h 17m
$438
ChicagoCali
ORD Chicago O'Hare Intl - CLO Cali Alfonso B. Aragon Intl
ORDCLO
Chicago O'Hare Intl
Mon 11/9
12:40 pm-5:55 am
2 stops16h 15m
Cali Alfonso B. Aragon Intl
Mon 11/16
12:05 pm-12:45 am
2 stops13h 40m
$461
ChicagoCali
ORD Chicago O'Hare Intl - CLO Cali Alfonso B. Aragon Intl
ORDCLO
Chicago O'Hare Intl
Fri 9/11
5:00 am-11:33 pm
2 stops18h 33m
Cali Alfonso B. Aragon Intl
Mon 9/14
8:48 am-9:09 am
2 stops24h 21m
$464
ChicagoCali
ORD Chicago O'Hare Intl - CLO Cali Alfonso B. Aragon Intl
ORDCLO
Chicago O'Hare Intl
Fri 10/23
3:20 pm-2:10 pm
1 stop22h 50m
Cali Alfonso B. Aragon Intl
Wed 10/28
12:09 pm-1:05 am
1 stop12h 56m
$470
ChicagoCali
ORD Chicago O'Hare Intl - CLO Cali Alfonso B. Aragon Intl
ORDCLO
Chicago O'Hare Intl
Wed 9/9
6:25 pm-9:00 am
2 stops14h 35m
Cali Alfonso B. Aragon Intl
Mon 9/14
8:48 am-12:59 am
2 stops16h 11m
$470
ChicagoCali
ORD Chicago O'Hare Intl - CLO Cali Alfonso B. Aragon Intl
ORDCLO
Chicago O'Hare Intl
Tue 11/24
2:13 pm-5:04 pm
1 stop25h 51m
Cali Alfonso B. Aragon Intl
Wed 12/2
12:02 pm-12:11 am
1 stop13h 09m
$470
ChicagoCali
ORD Chicago O'Hare Intl - CLO Cali Alfonso B. Aragon Intl
ORDCLO
Chicago O'Hare Intl
Fri 11/6
2:13 pm-5:32 pm
1 stop26h 19m
Cali Alfonso B. Aragon Intl
Mon 11/9
4:38 am-12:11 am
1 stop20h 33m
$470
Showing 1-10 of 18 resultsSorted by cheapest first
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 September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago-Cali flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Cali flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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.
CHI-CLO
ORD-CLO
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
CHI-CLO
ORD-CLO
What is the cheapest month to book a flight from Chicago to Cali?
Currently, February is the cheapest month in which you can book a flight from Chicago to Cali (average of $307). Flying from Chicago to Cali in December is currently the most expensive (average of $872). 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 83% 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 $457.
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: 8h 13m.
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 Panama City (PTY) offer the fastest connection on this route, with an average layover time of 1h 58m.
How far ahead should I book a flight from Chicago to Cali?
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 45 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
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 1, 2026.
Read reviews from past customers who have flown Copa Airlines,American Airlines, andAvianca 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.
Entertainment
6.8
Overall
7.6
Food
6.9
Crew
8.1
Boarding
7.8
Comfort
7.4
Reviews
1 / 20
2.0
MediocreAnonymous,Jul 2026
BOS - PTY
Entertainment
6.8
Overall
7.6
Food
6.9
Crew
8.1
Boarding
7.8
Comfort
7.4
Reviews
1 / 20
2.0
MediocreAnonymous,Jul 2026
BOS - PTY
Entertainment
6.8
Overall
7.6
Food
6.9
Crew
8.1
Boarding
7.8
Comfort
7.4
Reviews
1 / 20
2.0
MediocreAnonymous,Jul 2026
BOS - PTY
Entertainment
6.8
Overall
7.6
Food
6.9
Crew
8.1
Boarding
7.8
Comfort
7.4
Reviews
1 / 20
2.0
MediocreAnonymous,Jul 2026
BOS - PTY
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.
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Other flights to Cali
Explore flights to Cali departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 1, 2026.
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Chicago and Cali flights
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Other flights from Chicago
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Popular flight searches
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Top 3 airlines flying from Chicago to Cali
Discover the top 3 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 7,457,451 searches. Data last updated September 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$281 | Average$445 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$348 | Average$671 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$375 | Average$525 | FlexibilityNo cancel fee | On-time71% |