$106+ Cheap flights from Chicago (CHI) to Los Cabos
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 5/26. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJD
May 27 — Jun 31
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Los Cabos 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
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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 Los Cabos
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Cheapest flights from Chicago to Los CabosExplore the most affordable flight options available from Chicago to Los Cabos. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 27, 2026.
Explore the most affordable flight options available from Chicago to Los Cabos. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 27, 2026.
This FlightHub deal was found by Cheapflights users on 4/27. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/231:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Sat 10/313:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 4/27![Volaris logo]()
$379
This FlightHub deal was found by Cheapflights users on 4/22. 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.
Sun 5/37:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Sun 5/107:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 4/22![Volaris logo]()
$380
This FlightHub deal was found by Cheapflights users on 4/25. 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.
Tue 6/161:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Sun 6/213:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 4/25![Volaris logo]()
$381
This Viva deal was found by Cheapflights users on 4/22. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2912:20 pm
ORD
- SJD
1 stop19h 55m
Viva
Sun 5/37:40 am
SJD
- ORD
1 stop15h 05m
Viva
Deal found 4/22![Viva logo]()
$382
This Kiwi.com deal was found by Cheapflights users on 4/25. 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 5/37:35 am
ORD
- SJD
1 stop13h 29m
Multiple Airlines
Fri 5/88:40 am
SJD
- ORD
1 stop14h 05m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$383
This Kiwi.com deal was found by Cheapflights users on 4/26. 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.
Tue 5/267:35 am
ORD
- SJD
1 stop13h 29m
Multiple Airlines
Tue 6/21:10 pm
SJD
- ORD
1 stop8h 45m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$384
This Kiwi.com deal was found by Cheapflights users on 4/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/192:53 am
ORD
- SJD
1 stop10h 36m
Multiple Airlines
Thu 6/258:20 am
SJD
- ORD
1 stop13h 35m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$385
This Viva deal was found by Cheapflights users on 4/25. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/21:30 am
ORD
- SJD
1 stop8h 03m
Viva
Sat 10/107:55 pm
SJD
- ORD
1 stop13h 05m
Viva
Deal found 4/25![Viva logo]()
$386
This Justfly.com deal was found by Cheapflights users on 4/25. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/37:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Sun 6/77:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 4/25![Volaris logo]()
$387
This Viva deal was found by Cheapflights users on 4/26. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/71:30 am
ORD
- SJD
1 stop8h 00m
Viva
Fri 6/128:20 am
SJD
- ORD
1 stop13h 35m
Viva
Deal found 4/26![Viva logo]()
$388
This FlightHub deal was found by Cheapflights users on 4/24. 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.
Sat 5/237:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Tue 5/267:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 4/24![Volaris logo]()
$389
This Justfly.com deal was found by Cheapflights users on 4/22. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/27:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Sat 5/97:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 4/22![Volaris logo]()
$390
Best flights from Chicago to Los CabosDiscover carefully curated flight deals from Chicago to Los Cabos that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 27, 2026.
Discover carefully curated flight deals from Chicago to Los Cabos that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 27, 2026.
This Volaris deal was found by Cheapflights users on 4/22. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/157:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Tue 5/197:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 4/22![Volaris logo]()
$401
This Southwest deal was found by Cheapflights users on 4/24. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/65:15 am
MDW
- SJD
1 stop9h 05m
Southwest
Thu 7/910:40 am
SJD
- MDW
2 stops11h 55m
Southwest
Deal found 4/24![Southwest logo]()
$622
This Delta deal was found by Cheapflights users on 4/26. 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.
Sat 6/66:23 am
MDW
- SJD
1 stop8h 27m
Delta
Thu 6/1112:30 pm
SJD
- MDW
1 stop7h 47m
Delta
Deal found 4/26![Delta logo]()
$647
This Volaris deal was found by Cheapflights users on 4/26. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/202:53 am
ORD
- SJD
1 stop7h 23m
Volaris
Thu 6/257:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 4/26![Volaris logo]()
$403
This Volaris deal was found by Cheapflights users on 4/26. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/106:21 am
ORD
- SJD
1 stop10h 30m
Volaris
Wed 7/153:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 4/26![Volaris logo]()
$403
This Volaris deal was found by Cheapflights users on 4/26. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/162:53 am
ORD
- SJD
1 stop7h 23m
Volaris
Sun 6/217:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 4/26![Volaris logo]()
$411
This Volaris deal was found by Cheapflights users on 4/23. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/187:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Mon 6/227:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 4/23![Volaris logo]()
$431
This Delta deal was found by Cheapflights users on 4/25. 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.
Fri 7/106:00 am
MDW
- SJD
1 stop7h 11m
Delta
Wed 7/1512:16 pm
SJD
- MDW
1 stop7h 59m
Delta
Deal found 4/25![Delta logo]()
$647
This Volaris deal was found by Cheapflights users on 4/24. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/17:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Sat 8/87:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 4/24![Volaris logo]()
$450
This Southwest deal was found by Cheapflights users on 4/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/177:00 am
MDW
- SJD
1 stop7h 55m
Southwest
Mon 6/229:45 am
SJD
- MDW
2 stops10h 10m
Southwest
Deal found 4/26![Southwest logo]()
$689
This Volaris deal was found by Cheapflights users on 4/22. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/181:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Mon 5/257:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 4/22![Volaris logo]()
$452
This Southwest deal was found by Cheapflights users on 4/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/35:15 am
MDW
- SJD
1 stop9h 05m
Southwest
Sun 7/1211:05 am
SJD
- MDW
1 stop7h 45m
Southwest
Deal found 4/27![Southwest logo]()
$692
This Delta deal was found by Cheapflights users on 4/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/116:23 am
MDW
- SJD
2 stops13h 25m
Delta
Thu 5/146:07 am
SJD
- MDW
2 stops13h 02m
Delta
Deal found 4/27![Delta logo]()
$732
This Volaris deal was found by Cheapflights users on 4/26. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/171:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Thu 5/217:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 4/26![Volaris logo]()
$461
This Southwest deal was found by Cheapflights users on 4/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/235:15 am
MDW
- SJD
2 stops10h 25m
Southwest
Sun 7/261:55 pm
SJD
- MDW
1 stop13h 15m
Southwest
Deal found 4/22![Southwest logo]()
$697
This Southwest deal was found by Cheapflights users on 4/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/67:05 am
MDW
- SJD
1 stop9h 10m
Southwest
Sat 6/1311:05 am
SJD
- MDW
1 stop10h 05m
Southwest
Deal found 4/22![Southwest logo]()
$719
This Volaris deal was found by Cheapflights users on 4/23. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/86:21 am
ORD
- SJD
1 stop7h 08m
Volaris
Sat 7/117:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 4/23![Volaris logo]()
$492
This Volaris deal was found by Cheapflights users on 4/24. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/291:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Sun 8/27:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 4/24![Volaris logo]()
$500
This Southwest deal was found by Cheapflights users on 4/24. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/225:30 am
MDW
- SJD
2 stops8h 40m
Southwest
Fri 5/291:55 pm
SJD
- MDW
1 stop12h 40m
Southwest
Deal found 4/24![Southwest logo]()
$741
This Southwest deal was found by Cheapflights users on 4/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/45:30 am
MDW
- SJD
2 stops8h 40m
Southwest
Mon 5/1112:25 pm
SJD
- MDW
2 stops8h 20m
Southwest
Deal found 4/22![Southwest logo]()
$797
Last-minute flights from Chicago to Los CabosDiscover last-minute flight deals from Chicago to Los Cabos. Data last updated April 27, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Los Cabos. Data last updated April 27, 2026 and is based on user searches.
This Viva deal was found by Cheapflights users on 4/22. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2912:20 pm
ORD
- SJD
1 stop19h 55m
Viva
Sun 5/37:40 am
SJD
- ORD
1 stop15h 05m
Viva
Deal found 4/22![Viva logo]()
$382
This Justfly.com deal was found by Cheapflights users on 4/22. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/27:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Sat 5/97:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 4/22![Volaris logo]()
$390
This FlightHub deal was found by Cheapflights users on 4/22. 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.
Sun 5/37:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Sun 5/107:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 4/22![Volaris logo]()
$380
This Kiwi.com deal was found by Cheapflights users on 4/25. 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 5/37:35 am
ORD
- SJD
1 stop13h 29m
Multiple Airlines
Fri 5/88:40 am
SJD
- ORD
1 stop14h 05m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$383
This Gotogate deal was found by Cheapflights users on 4/22. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/47:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Mon 5/117:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 4/22![Volaris logo]()
$391
This Justfly.com deal was found by Cheapflights users on 4/22. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/41:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Fri 5/812:02 pm
SJD
- ORD
1 stop9h 45m
Volaris
Deal found 4/22![Volaris logo]()
$395
This Kiwi.com deal was found by Cheapflights users on 4/26. 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.
Tue 5/51:40 am
ORD
- SJD
1 stop10h 29m
Multiple Airlines
Tue 5/128:05 am
SJD
- ORD
2 stops14h 50m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$393
This Kiwi.com deal was found by Cheapflights users on 4/26. 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 5/67:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Mon 5/117:37 pm
SJD
- ORD
2 stops27h 18m
Volaris
Deal found 4/26![Volaris logo]()
$392
This Kiwi.com deal was found by Cheapflights users on 4/25. 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.
Thu 5/77:35 am
ORD
- SJD
1 stop13h 29m
Multiple Airlines
Sun 5/101:05 pm
SJD
- ORD
1 stop9h 50m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$398
This FlightHub deal was found by Cheapflights users on 4/22. 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 5/147:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Sun 5/177:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 4/22![Volaris logo]()
$394
This FlightHub deal was found by Cheapflights users on 4/24. 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.
Sat 5/237:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Tue 5/267:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 4/24![Volaris logo]()
$389
This Kiwi.com deal was found by Cheapflights users on 4/26. 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.
Tue 5/267:35 am
ORD
- SJD
1 stop13h 29m
Multiple Airlines
Tue 6/21:10 pm
SJD
- ORD
1 stop8h 45m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$384
One-way flights from Chicago to Los CabosSearch for one-way flight options from Chicago to Los Cabos. Find affordable one-way fares based on user searches. Data last updated April 27, 2026.
Search for one-way flight options from Chicago to Los Cabos. Find affordable one-way fares based on user searches. Data last updated April 27, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/267:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Deal found 4/27![Volaris logo]()
$106
This Kiwi.com deal was found by Cheapflights users on 4/24. 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 6/261:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Deal found 4/24![Volaris logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 4/22. 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 6/202:53 am
ORD
- SJD
1 stop7h 23m
Volaris
Deal found 4/22![Volaris logo]()
$115
This FlightHub deal was found by Cheapflights users on 4/25. 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.
Wed 5/67:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Deal found 4/25![Volaris logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 4/26. 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 5/47:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Deal found 4/26![Volaris logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 4/24. 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.
Tue 6/232:53 am
ORD
- SJD
1 stop7h 23m
Volaris
Deal found 4/24![Volaris logo]()
$129
This Mytrip deal was found by Cheapflights users on 4/26. 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 5/21:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Deal found 4/26![Volaris logo]()
$131
This Kiwi.com deal was found by Cheapflights users on 4/24. 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 5/181:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Deal found 4/24![Volaris logo]()
$132
This FlightHub deal was found by Cheapflights users on 4/22. 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.
Sat 6/68:49 pm
MDW
- SJD
1 stop13h 27m
Volaris
Deal found 4/22![Volaris logo]()
$159
This FlightHub deal was found by Cheapflights users on 4/25. 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.
Sat 6/278:49 pm
MDW
- SJD
1 stop13h 27m
Volaris
Deal found 4/25![Volaris logo]()
$170
This FlightHub deal was found by Cheapflights users on 4/23. 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 6/188:49 pm
MDW
- SJD
1 stop13h 27m
Volaris
Deal found 4/23![Volaris logo]()
$184
This Volaris deal was found by Cheapflights users on 4/24. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/238:49 pm
MDW
- SJD
1 stop13h 27m
Volaris
Deal found 4/24![Volaris logo]()
$226
Find flight deals from Chicago to Los Cabos
Keep the following information in mind while searching for Chicago to Los Cabos flight deals. Data was last updated April 27, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $371 (Kiwi.com) |
One-way from | $106 (Kiwi.com) |
Popular in | March |
Cheapest in | September |
Average price | $564 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Los Cabos 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 27, 2026.
Use the filters below to find and compare flights from Chicago to Los Cabos that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Fri 5/15
7:35 am-7:04 pm
1 stop13h 29m
San José del Cabo Los Cabos
Tue 5/19
7:47 pm-5:52 am
1 stop8h 05m
$401
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Sat 6/20
2:53 am-8:16 am
1 stop7h 23m
San José del Cabo Los Cabos
Thu 6/25
7:47 pm-5:52 am
1 stop8h 05m
$403
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Fri 7/10
6:21 am-2:51 pm
1 stop10h 30m
San José del Cabo Los Cabos
Wed 7/15
3:36 pm-12:55 am
1 stop7h 19m
$403
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Tue 6/16
2:53 am-8:16 am
1 stop7h 23m
San José del Cabo Los Cabos
Sun 6/21
7:47 pm-5:52 am
1 stop8h 05m
$411
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Thu 6/18
7:35 am-7:04 pm
1 stop13h 29m
San José del Cabo Los Cabos
Mon 6/22
7:47 pm-5:52 am
1 stop8h 05m
$431
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Sat 8/1
7:35 am-7:04 pm
1 stop13h 29m
San José del Cabo Los Cabos
Sat 8/8
7:47 pm-5:52 am
1 stop8h 05m
$450
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Mon 5/18
1:40 am-10:09 am
1 stop10h 29m
San José del Cabo Los Cabos
Mon 5/25
7:47 pm-5:52 am
1 stop8h 05m
$452
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Sun 5/17
1:40 am-10:09 am
1 stop10h 29m
San José del Cabo Los Cabos
Thu 5/21
7:47 pm-5:52 am
1 stop8h 05m
$461
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Wed 7/8
6:21 am-11:29 am
1 stop7h 08m
San José del Cabo Los Cabos
Sat 7/11
7:47 pm-5:52 am
1 stop8h 05m
$492
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Wed 7/29
1:40 am-10:09 am
1 stop10h 29m
San José del Cabo Los Cabos
Sun 8/2
7:47 pm-5:52 am
1 stop8h 05m
$500
Showing 1-10 of 40 resultsSorted by cheapest first
Best time to book a flight from Chicago to Los Cabos
Have a flexible travel schedule? Discover the best time to fly to Los Cabos from Chicago with our price prediction graph.
ORD-SJD
MDW-SJD
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 Los Cabos
CHI-zzKPG
ORD-SJD
MDW-SJD
How far ahead should I book a flight from Chicago to Los Cabos?
The best time to book flights from Chicago to Los Cabos is 32 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest month to book a flight from Chicago to Los Cabos?
Currently, February is the cheapest month in which you can book a flight from Chicago to Los Cabos (average of $131). Flying from Chicago to Los Cabos in March is currently the most expensive (average of $1,110). 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 KPG?
Find hourly flight availability from Chicago to Los Cabos. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 27, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Los Cabos as you normally would.
Weekly flight availability from Chicago to Los Cabos
Explore weekly flight availability from Chicago to Los Cabos. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated April 27, 2026.
The most flights from CHI to zzKPG are scheduled on a Monday (3 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (1 on average).
Reviews of airlines servicing Los Cabos
Get insights into the airlines that provide service to Los Cabos. 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 Los Cabos. Reviews last updated April 27, 2026.
Peruse reviews from past customers who have flown with Southwest,Delta, andUnited Airlines from Chicago to Los Cabos to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from Chicago to Los Cabos. 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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Alternative routes for Chicago to Los Cabos
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Complete your trip
Complete your trip to Los Cabos by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Los Cabos by cabin class
Find flights from Chicago to Los Cabos, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Los Cabos flights
Browse other Chicago and Los Cabos flight options. Last updated on April 27, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 6 airlines flying from Chicago to Los Cabos
Discover the top 6 airlines that operate flights from Chicago to Los Cabos. 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 27, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$184 | Average$527 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$185 | Average$387 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$318 | Average$470 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$412 | Average$623 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$416 | Average$618 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$475 | Average$694 | FlexibilityNo cancel fee | On-time63% |