$127+ 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 5/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CLO
May 14 — May 211
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Cali with Cheapflights
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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
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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 April 14, 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 April 14, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/9. 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 5/17:15 pm
ORD
- CLO
1 stop17h 43m
Multiple Airlines
Thu 5/79:26 pm
CLO
- ORD
2 stops26h 33m
Multiple Airlines
Deal found 4/9![Multiple Airlines logo]()
$375
This Mytrip deal was found by Cheapflights users on 4/10. 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.
Tue 4/217:15 pm
ORD
- CLO
1 stop17h 43m
Spirit Airlines
Fri 4/241:53 pm
CLO
- ORD
1 stop10h 31m
Spirit Airlines
Deal found 4/10![Spirit Airlines logo]()
$395
This Cheapflightsfares deal was found by Cheapflights users on 4/13. 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.
Fri 5/87:33 pm
ORD
- CLO
1 stop17h 34m
Spirit Airlines
Wed 5/132:02 pm
CLO
- ORD
1 stop18h 20m
Spirit Airlines
Deal found 4/13![Spirit Airlines logo]()
$401
This Kiwi.com deal was found by Cheapflights users on 4/12. 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 5/154:05 pm
ORD
- CLO
1 stop21h 02m
Multiple Airlines
Tue 5/197:25 pm
CLO
- ORD
2 stops41h 12m
Multiple Airlines
Deal found 4/12![Multiple Airlines logo]()
$411
This oojo deal was found by Cheapflights users on 4/9. 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.
Sat 4/1111:20 pm
ORD
- CLO
1 stop13h 55m
Avianca
Wed 4/158:00 am
CLO
- ORD
1 stop13h 20m
Avianca
Deal found 4/9![Avianca logo]()
$421
This Kiwi.com deal was found by Cheapflights users on 4/13. 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 5/103:44 pm
ORD
- CLO
2 stops46h 11m
Multiple Airlines
Sat 5/162:02 pm
CLO
- ORD
1 stop9h 13m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$425
This Cheapflightsfares deal was found by Cheapflights users on 4/11. 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 5/95:05 am
ORD
- CLO
1 stop8h 02m
Spirit Airlines
Sat 5/162:02 pm
CLO
- ORD
1 stop9h 13m
Spirit Airlines
Deal found 4/11![Spirit Airlines logo]()
$436
This Vliegwinkel deal was found by Cheapflights users on 4/13. 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 Vliegwinkel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2711:20 pm
ORD
- CLO
1 stop14h 50m
Avianca
Tue 5/56:15 am
CLO
- ORD
1 stop15h 05m
Avianca
Deal found 4/13![Avianca logo]()
$439
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 April 14, 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 April 14, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/9. 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 5/17:15 pm
ORD
- CLO
1 stop17h 43m
Multiple Airlines
Thu 5/79:26 pm
CLO
- ORD
2 stops26h 33m
Multiple Airlines
Deal found 4/9![Multiple Airlines logo]()
$375
This American Airlines deal was found by Cheapflights users on 4/9. 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.
Sun 5/246:08 am
ORD
- CLO
1 stop14h 52m
American Airlines
Sun 5/3111:59 pm
CLO
- ORD
1 stop9h 11m
American Airlines
Deal found 4/9![American Airlines logo]()
$475
This Copa Airlines deal was found by Cheapflights users on 4/9. 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 7/68:02 am
ORD
- CLO
1 stop9h 33m
Copa Airlines
Fri 7/1012:06 pm
CLO
- ORD
1 stop15h 54m
Copa Airlines
Deal found 4/9![Copa Airlines logo]()
$483
This Avianca deal was found by Cheapflights users on 4/9. 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.
Sat 4/1811:20 pm
ORD
- CLO
1 stop9h 40m
Avianca
Wed 4/228:25 am
CLO
- ORD
1 stop12h 55m
Avianca
Deal found 4/9![Avianca logo]()
$489
This Mytrip deal was found by Cheapflights users on 4/11. 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.
Sat 5/95:05 am
ORD
- CLO
2 stops16h 00m
Multiple Airlines
Sat 5/162:02 pm
CLO
- ORD
2 stops22h 21m
Multiple Airlines
Deal found 4/11![Multiple Airlines logo]()
$479
This Avianca deal was found by Cheapflights users on 4/13. 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.
Sun 5/311:20 pm
ORD
- CLO
1 stop14h 50m
Avianca
Thu 5/78:00 am
CLO
- ORD
1 stop13h 20m
Avianca
Deal found 4/13![Avianca logo]()
$489
This oojo deal was found by Cheapflights users on 4/10. 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.
Sat 4/2511:20 pm
ORD
- CLO
1 stop13h 05m
Avianca
Sun 5/39:20 pm
CLO
- ORD
1 stop24h 00m
Avianca
Deal found 4/10![Avianca logo]()
$491
This American Airlines deal was found by Cheapflights users on 4/9. 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.
Mon 7/64:05 pm
ORD
- CLO
1 stop21h 10m
American Airlines
Fri 7/1011:59 pm
CLO
- ORD
2 stops14h 21m
American Airlines
Deal found 4/9![American Airlines logo]()
$566
This Mytrip deal was found by Cheapflights users on 4/9. 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.
Sun 5/247:33 pm
ORD
- CLO
1 stop17h 34m
Multiple Airlines
Sun 5/317:53 pm
CLO
- ORD
3 stops27h 22m
Multiple Airlines
Deal found 4/9![Multiple Airlines logo]()
$544
This oojo deal was found by Cheapflights users on 4/12. 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.
Fri 4/2411:20 pm
ORD
- CLO
1 stop13h 05m
Avianca
Sun 4/267:00 am
CLO
- ORD
1 stop14h 20m
Avianca
Deal found 4/12![Avianca logo]()
$511
This Mytrip deal was found by Cheapflights users on 4/10. 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.
Fri 4/246:40 am
ORD
- CLO
3 stops30h 18m
Multiple Airlines
Mon 4/275:00 am
CLO
- ORD
3 stops19h 24m
Multiple Airlines
Deal found 4/10![Multiple Airlines logo]()
$572
This Avianca deal was found by Cheapflights users on 4/13. 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.
Wed 5/207:14 am
ORD
- CLO
2 stops12h 46m
Avianca
Sat 6/208:25 am
CLO
- ORD
1 stop12h 55m
Avianca
Deal found 4/13![Avianca logo]()
$581
Last-minute flights from Chicago to CaliDiscover last-minute flight deals from Chicago to Cali. Data last updated April 14, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Cali. Data last updated April 14, 2026 and is based on user searches.
This Mytrip deal was found by Cheapflights users on 4/10. 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.
Tue 4/217:15 pm
ORD
- CLO
1 stop17h 43m
Spirit Airlines
Fri 4/241:53 pm
CLO
- ORD
1 stop10h 31m
Spirit Airlines
Deal found 4/10![Spirit Airlines logo]()
$395
This American Airlines deal was found by Cheapflights users on 4/10. 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 4/219:01 pm
ORD
- CLO
2 stops16h 07m
American Airlines
Fri 4/242:15 pm
CLO
- ORD
2 stops18h 15m
American Airlines
Deal found 4/10![American Airlines logo]()
$450
This Mytrip deal was found by Cheapflights users on 4/10. 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.
Tue 4/217:15 pm
ORD
- CLO
3 stops27h 40m
Multiple Airlines
Fri 4/246:15 am
CLO
- ORD
2 stops18h 09m
Multiple Airlines
Deal found 4/10![Multiple Airlines logo]()
$461
This oojo deal was found by Cheapflights users on 4/12. 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.
Thu 4/2311:20 pm
ORD
- CLO
1 stop13h 05m
Avianca
Mon 4/279:20 pm
CLO
- ORD
1 stop24h 00m
Avianca
Deal found 4/12![Avianca logo]()
$441
This BusinessClass deal was found by Cheapflights users on 4/12. 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 BusinessClass is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/238:46 pm
ORD
- CLO
2 stops16h 22m
GOL
Mon 4/272:15 pm
CLO
- ORD
2 stops19h 56m
GOL
Deal found 4/12![GOL logo]()
$557
This American Airlines deal was found by Cheapflights users on 4/12. 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 4/238:46 pm
ORD
- CLO
2 stops16h 22m
American Airlines
Mon 4/272:15 pm
CLO
- ORD
1 stop23h 01m
American Airlines
Deal found 4/12![American Airlines logo]()
$568
This American Airlines deal was found by Cheapflights users on 4/10. 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.
Fri 4/248:46 pm
ORD
- CLO
2 stops16h 22m
American Airlines
Mon 4/272:15 pm
CLO
- ORD
1 stop21h 56m
American Airlines
Deal found 4/10![American Airlines logo]()
$501
This oojo deal was found by Cheapflights users on 4/12. 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.
Fri 4/2411:20 pm
ORD
- CLO
1 stop13h 05m
Avianca
Sun 4/267:00 am
CLO
- ORD
1 stop14h 20m
Avianca
Deal found 4/12![Avianca logo]()
$511
This CheapOair deal was found by Cheapflights users on 4/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/2411:28 am
ORD
- CLO
2 stops25h 30m
Spirit Airlines
Mon 4/271:53 pm
CLO
- ORD
2 stops20h 30m
Spirit Airlines
Deal found 4/10![Spirit Airlines logo]()
$515
This Mytrip deal was found by Cheapflights users on 4/10. 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.
Fri 4/2411:28 am
ORD
- CLO
2 stops25h 30m
Multiple Airlines
Mon 4/275:00 am
CLO
- ORD
3 stops19h 24m
Multiple Airlines
Deal found 4/10![Multiple Airlines logo]()
$530
This Kiwi.com deal was found by Cheapflights users on 4/12. 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 4/245:05 am
ORD
- CLO
1 stop7h 53m
Multiple Airlines
Sun 4/266:15 am
CLO
- ORD
2 stops17h 40m
Multiple Airlines
Deal found 4/12![Multiple Airlines logo]()
$543
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 April 14, 2026.
Search for one-way flight options from Chicago to Cali. Find affordable one-way fares based on user searches. Data last updated April 14, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/12. 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.
Mon 5/115:05 am
ORD
- CLO
1 stop8h 02m
Spirit Airlines
Deal found 4/12![Spirit Airlines logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 4/12. 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 5/278:05 am
ORD
- CLO
2 stops35h 23m
Multiple Airlines
Deal found 4/12![Multiple Airlines logo]()
$133
This oojo deal was found by Cheapflights users on 4/12. 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 5/2711:20 pm
ORD
- CLO
1 stop13h 05m
Avianca
Deal found 4/12![Avianca logo]()
$171
This oojo deal was found by Cheapflights users on 4/14. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/2511:20 pm
ORD
- CLO
1 stop9h 40m
Avianca
Deal found 4/14![Avianca logo]()
$172
This Mytrip deal was found by Cheapflights users on 4/12. 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.
Mon 5/115:05 am
ORD
- CLO
3 stops25h 10m
Multiple Airlines
Deal found 4/12![Multiple Airlines logo]()
$188
This oojo deal was found by Cheapflights users on 4/13. 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.
Tue 8/255:15 pm
ORD
- CLO
2 stops28h 00m
Avianca
Deal found 4/13![Avianca logo]()
$195
This Avianca deal was found by Cheapflights users on 4/13. 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 4/2311:20 pm
ORD
- CLO
1 stop13h 05m
Avianca
Deal found 4/13![Avianca logo]()
$202
This eDestinos deal was found by Cheapflights users on 4/13. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/185:15 am
ORD
- CLO
2 stops12h 50m
LATAM Airlines
Deal found 4/13![LATAM Airlines logo]()
$206
This Copa Airlines deal was found by Cheapflights users on 4/13. 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 7/311:20 am
ORD
- CLO
1 stop16h 13m
Copa Airlines
Deal found 4/13![Copa Airlines logo]()
$214
This American Airlines deal was found by Cheapflights users on 4/9. 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.
Sat 8/16:10 am
ORD
- CLO
1 stop14h 50m
American Airlines
Deal found 4/9![American Airlines logo]()
$222
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 April 14, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $375 (Kiwi.com) |
One-way from | $127 (Kiwi.com) |
Popular in | December |
Cheapest in | September |
Average price | $398 |
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 April 14, 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 - CLO
ORDCLO
Chicago O'Hare Intl
Fri 5/1
7:15 pm-12:58 pm
1 stop17h 43m
Cali Alfonso B. Aragon Intl
Thu 5/7
9:26 pm-11:59 pm
2 stops26h 33m
$375
ChicagoCali
ORD - CLO
ORDCLO
Chicago O'Hare Intl
Sun 5/24
6:08 am-9:00 pm
1 stop14h 52m
Cali Alfonso B. Aragon Intl
Sun 5/31
11:59 pm-9:10 am
1 stop9h 11m
$475
ChicagoCali
ORD - CLO
ORDCLO
Chicago O'Hare Intl
Sat 5/9
5:05 am-9:05 pm
2 stops16h 00m
Cali Alfonso B. Aragon Intl
Sat 5/16
2:02 pm-12:23 pm
2 stops22h 21m
$479
ChicagoCali
ORD - CLO
ORDCLO
Chicago O'Hare Intl
Mon 7/6
8:02 am-5:35 pm
1 stop9h 33m
Cali Alfonso B. Aragon Intl
Fri 7/10
12:06 pm-4:00 am
1 stop15h 54m
$483
Quickest round-trip
ChicagoCali
ORD - CLO
ORDCLO
Chicago O'Hare Intl
Sat 4/18
11:20 pm-9:00 am
1 stop9h 40m
Cali Alfonso B. Aragon Intl
Wed 4/22
8:25 am-9:20 pm
1 stop12h 55m
$489
ChicagoCali
ORD - CLO
ORDCLO
Chicago O'Hare Intl
Sun 5/3
11:20 pm-2:10 pm
1 stop14h 50m
Cali Alfonso B. Aragon Intl
Thu 5/7
8:00 am-9:20 pm
1 stop13h 20m
$489
ChicagoCali
ORD - CLO
ORDCLO
Chicago O'Hare Intl
Sat 4/25
11:20 pm-12:25 pm
1 stop13h 05m
Cali Alfonso B. Aragon Intl
Sun 5/3
9:20 pm-9:20 pm
1 stop24h 00m
$491
ChicagoCali
ORD - CLO
ORDCLO
Chicago O'Hare Intl
Fri 4/24
11:20 pm-12:25 pm
1 stop13h 05m
Cali Alfonso B. Aragon Intl
Sun 4/26
7:00 am-9:20 pm
1 stop14h 20m
$511
ChicagoCali
ORD - CLO
ORDCLO
Chicago O'Hare Intl
Sun 5/24
7:33 pm-1:07 pm
1 stop17h 34m
Cali Alfonso B. Aragon Intl
Sun 5/31
7:53 pm-11:15 pm
3 stops27h 22m
$544
ChicagoCali
ORD - CLO
ORDCLO
Chicago O'Hare Intl
Mon 7/6
4:05 pm-1:15 pm
1 stop21h 10m
Cali Alfonso B. Aragon Intl
Fri 7/10
11:59 pm-2:20 pm
2 stops14h 21m
$566
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 April.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*2 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
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 April 10, 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 3 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 June is currently the most expensive (average of $384). 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.
How much does it cost to fly round-trip from Chicago to Cali?
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 94% 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.
Panama City (PTY) is the most affordable 1-stop option, with an average round-trip price of $873.
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 2h 03m.
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 April 14, 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.
Overall
7.5
Comfort
7.4
Crew
8.1
Boarding
7.8
Entertainment
6.8
Food
6.8
Reviews
1 / 20
2.0
MediocreKaterine,Mar 2026
LAX - PTY
Overall
7.5
Comfort
7.4
Crew
8.1
Boarding
7.8
Entertainment
6.8
Food
6.8
Reviews
1 / 20
2.0
MediocreKaterine,Mar 2026
LAX - PTY
Overall
7.5
Comfort
7.4
Crew
8.1
Boarding
7.8
Entertainment
6.8
Food
6.8
Reviews
1 / 20
2.0
MediocreKaterine,Mar 2026
LAX - PTY
Overall
7.5
Comfort
7.4
Crew
8.1
Boarding
7.8
Entertainment
6.8
Food
6.8
Reviews
1 / 20
2.0
MediocreKaterine,Mar 2026
LAX - PTY
Overall
7.5
Comfort
7.4
Crew
8.1
Boarding
7.8
Entertainment
6.8
Food
6.8
Reviews
1 / 20
2.0
MediocreKaterine,Mar 2026
LAX - 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.
Browse thousands of different options on Cheapflights for your next trip
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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 April 14, 2026.
Complete your trip
Complete your trip to Cali by adding a car rental and/or hotel reservation to your travel itinerary.
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Chicago and Cali flights
Browse other Chicago and Cali flight options. Last updated on April 14, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on April 14, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 4 airlines flying from Chicago to Cali
Discover the top 4 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 April 14, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$126 | Average$341 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$288 | Average$432 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$295 | Average$603 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$330 | Average$543 | FlexibilityNo cancel fee | On-time71% |