$94+ 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 5/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJD
May 10 — May 171
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 10, 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 10, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/287:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Thu 6/47:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 4/7![Volaris logo]()
$412
This Mytrip deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/97:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Sat 5/167:37 pm
SJD
- ORD
2 stops14h 32m
Volaris
Deal found 4/8![Volaris logo]()
$414
This Kiwi.com deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/77:35 am
ORD
- SJD
1 stop13h 29m
Multiple Airlines
Sun 5/107:50 pm
SJD
- ORD
3 stops17h 53m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$415
This Trip.com deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/127:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Fri 4/177:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 4/7![Volaris logo]()
$416
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.
Mon 4/277:35 am
ORD
- SJD
1 stop13h 29m
Multiple Airlines
Wed 5/61:05 pm
SJD
- ORD
1 stop8h 40m
Multiple Airlines
Deal found 4/9![Multiple Airlines logo]()
$417
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.
Tue 4/282:35 am
ORD
- SJD
1 stop11h 50m
Multiple Airlines
Thu 5/78:40 am
SJD
- ORD
1 stop14h 05m
Multiple Airlines
Deal found 4/9![Multiple Airlines logo]()
$418
This Volaris 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/281:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Wed 8/57:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 4/9![Volaris logo]()
$419
This Volaris deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/137:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Sun 5/177:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 4/7![Volaris logo]()
$420
This Kiwi.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/102:53 am
ORD
- SJD
1 stop10h 36m
Multiple Airlines
Thu 6/117:55 pm
SJD
- ORD
1 stop7h 57m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$421
This Trip.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/117:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Sat 4/183:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 4/6![Volaris logo]()
$422
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 4/241:40 am
ORD
- SJD
1 stop10h 29m
Multiple Airlines
Thu 5/78:40 am
SJD
- ORD
1 stop14h 05m
Multiple Airlines
Deal found 4/9![Multiple Airlines logo]()
$423
This Kiwi.com deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/52:35 am
ORD
- SJD
1 stop10h 57m
Volaris
Tue 5/127:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 4/8![Volaris logo]()
$424
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 10, 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 10, 2026.
This Volaris deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/252:53 am
ORD
- SJD
1 stop7h 23m
Volaris
Mon 6/2912:02 pm
SJD
- ORD
1 stop9h 45m
Volaris
Deal found 4/8![Volaris logo]()
$419
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/203:45 pm
ORD
- SJD
1 stop8h 43m
Delta
Wed 5/2710:24 am
SJD
- ORD
2 stops11h 35m
Delta
Deal found 4/9![Delta logo]()
$472
This Viva deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/302:15 am
ORD
- SJD
1 stop18h 45m
Viva
Sun 5/37:40 am
SJD
- ORD
1 stop15h 05m
Viva
Deal found 4/6![Viva logo]()
$473
This Southwest deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/105:25 am
MDW
- SJD
1 stop10h 15m
Southwest
Mon 6/1510:40 am
SJD
- MDW
2 stops11h 55m
Southwest
Deal found 4/6![Southwest logo]()
$666
This Volaris deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Volaris 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 4/5![Volaris logo]()
$430
This Volaris 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/277:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Sun 5/317:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 4/10![Volaris logo]()
$440
This Delta deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/2910:08 am
ORD
- SJD
2 stops14h 22m
Delta
Wed 8/510:10 am
SJD
- ORD
1 stop9h 37m
Delta
Deal found 4/5![Delta logo]()
$498
This Viva deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/131:30 am
ORD
- SJD
1 stop21h 00m
Viva
Mon 7/208:25 am
SJD
- ORD
1 stop13h 30m
Viva
Deal found 4/5![Viva logo]()
$531
This Volaris deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/28:49 pm
MDW
- SJD
1 stop13h 27m
Volaris
Fri 6/58:50 am
SJD
- MDW
1 stop8h 14m
Volaris
Deal found 4/6![Volaris logo]()
$457
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/266:00 am
MDW
- SJD
2 stops13h 49m
Delta
Wed 4/2912:36 pm
SJD
- MDW
1 stop7h 52m
Delta
Deal found 4/9![Delta logo]()
$504
This Volaris 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/97:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Sat 5/167:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 4/9![Volaris logo]()
$465
This Delta deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/57:07 am
ORD
- SJD
2 stops17h 19m
Delta
Tue 6/161:43 pm
SJD
- ORD
2 stops16h 22m
Delta
Deal found 4/5![Delta logo]()
$526
This Southwest deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/255:45 am
MDW
- SJD
1 stop7h 15m
Southwest
Mon 6/2910:40 am
SJD
- MDW
2 stops11h 55m
Southwest
Deal found 4/5![Southwest logo]()
$669
This Volaris deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/227:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Mon 5/257:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 4/5![Volaris logo]()
$473
This Delta deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/301:57 am
ORD
- SJD
1 stop9h 28m
Delta
Wed 8/510:10 am
SJD
- ORD
1 stop9h 37m
Delta
Deal found 4/5![Delta logo]()
$539
This Southwest deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/25:05 am
MDW
- SJD
1 stop7h 15m
Southwest
Thu 7/92:35 pm
SJD
- MDW
1 stop8h 00m
Southwest
Deal found 4/5![Southwest logo]()
$669
This Volaris deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/231:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Sun 6/287:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 4/7![Volaris logo]()
$479
This Delta deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/276:00 am
MDW
- SJD
1 stop7h 31m
Delta
Fri 5/112:36 pm
SJD
- MDW
1 stop7h 52m
Delta
Deal found 4/7![Delta logo]()
$544
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/296:00 am
MDW
- SJD
1 stop8h 30m
Southwest
Tue 6/22:20 pm
SJD
- MDW
2 stops13h 05m
Southwest
Deal found 4/9![Southwest logo]()
$684
This Delta deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/211:18 am
MDW
- SJD
2 stops13h 10m
Delta
Thu 5/76:07 am
SJD
- MDW
2 stops13h 02m
Delta
Deal found 4/7![Delta logo]()
$624
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/196:23 am
MDW
- SJD
2 stops13h 25m
Delta
Sun 5/246:02 am
SJD
- MDW
2 stops13h 07m
Delta
Deal found 4/9![Delta logo]()
$681
This Delta deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/136:00 am
MDW
- SJD
1 stop7h 31m
Delta
Tue 4/1412:36 pm
SJD
- MDW
2 stops18h 11m
Delta
Deal found 4/7![Delta logo]()
$689
This Delta deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/910:45 am
MDW
- SJD
2 stops13h 33m
Delta
Sat 5/166:07 am
SJD
- MDW
2 stops13h 02m
Delta
Deal found 4/5![Delta logo]()
$694
Last-minute flights from Chicago to Los CabosDiscover last-minute flight deals from Chicago to Los Cabos. Data last updated April 10, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Los Cabos. Data last updated April 10, 2026 and is based on user searches.
This Trip.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/117:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Sat 4/183:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 4/6![Volaris logo]()
$422
This Trip.com deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/127:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Fri 4/177:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 4/7![Volaris logo]()
$416
This Volaris deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/167:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Wed 4/227:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 4/6![Volaris logo]()
$421
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 4/241:40 am
ORD
- SJD
1 stop10h 29m
Multiple Airlines
Fri 5/88:40 am
SJD
- ORD
1 stop14h 05m
Multiple Airlines
Deal found 4/9![Multiple Airlines logo]()
$423
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.
Mon 4/277:35 am
ORD
- SJD
1 stop13h 29m
Multiple Airlines
Wed 5/61:05 pm
SJD
- ORD
1 stop8h 40m
Multiple Airlines
Deal found 4/9![Multiple Airlines logo]()
$417
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.
Mon 4/271:40 am
ORD
- SJD
1 stop10h 29m
Multiple Airlines
Sun 5/37:40 am
SJD
- ORD
1 stop15h 05m
Multiple Airlines
Deal found 4/9![Multiple Airlines logo]()
$419
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.
Tue 4/282:35 am
ORD
- SJD
1 stop11h 50m
Multiple Airlines
Thu 5/78:40 am
SJD
- ORD
1 stop14h 05m
Multiple Airlines
Deal found 4/9![Multiple Airlines logo]()
$418
This Kiwi.com deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/52:35 am
ORD
- SJD
1 stop10h 57m
Volaris
Tue 5/127:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 4/8![Volaris logo]()
$424
This Kiwi.com deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/77:35 am
ORD
- SJD
1 stop13h 29m
Multiple Airlines
Sun 5/107:50 pm
SJD
- ORD
3 stops17h 53m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$415
This Mytrip deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/97:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Sat 5/167:37 pm
SJD
- ORD
2 stops14h 32m
Volaris
Deal found 4/8![Volaris logo]()
$414
This Volaris deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/137:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Sun 5/177:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 4/7![Volaris logo]()
$420
This Cheapflightsfares deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/287:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Thu 6/47:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 4/7![Volaris logo]()
$412
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 10, 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 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
Volaris
Deal found 4/8![Volaris logo]()
$94
This Kiwi.com deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/277:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Deal found 4/8![Volaris logo]()
$104
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/62:53 am
ORD
- SJD
1 stop10h 36m
Volaris
Deal found 4/10![Volaris logo]()
$107
This Trip.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.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
Deal found 4/5![Volaris logo]()
$111
This Trip.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/57:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Deal found 4/5![Volaris logo]()
$114
This Trip.com deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/161:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Deal found 4/7![Volaris logo]()
$121
This Trip.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/181:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Deal found 4/6![Volaris logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/101:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Deal found 4/8![Volaris logo]()
$124
This Kiwi.com deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/93:07 pm
MDW
- SJD
3 stops45h 46m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$190
This Cheapflightsfares deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/138:49 pm
MDW
- SJD
1 stop13h 27m
Volaris
Deal found 4/7![Volaris logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/63:07 pm
MDW
- SJD
3 stops45h 46m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$199
This Kiwi.com deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/46:20 am
MDW
- SJD
3 stops29h 49m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$202
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 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $412 (Cheapflightsfares) |
One-way from | $94 (Kiwi.com) |
Popular in | March |
Cheapest in | September |
Average price | $562 |
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 10, 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
Thu 6/25
2:53 am-8:16 am
1 stop7h 23m
San José del Cabo Los Cabos
Mon 6/29
12:02 pm-11:47 pm
1 stop9h 45m
$419
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Sun 5/3
7:35 am-7:04 pm
1 stop13h 29m
San José del Cabo Los Cabos
Sun 5/10
7:47 pm-5:52 am
1 stop8h 05m
$430
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Wed 5/27
7:35 am-7:04 pm
1 stop13h 29m
San José del Cabo Los Cabos
Sun 5/31
7:47 pm-5:52 am
1 stop8h 05m
$440
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Tue 6/2
8:49 pm-8:16 am
1 stop13h 27m
San José del Cabo Los Cabos
Fri 6/5
8:50 am-7:04 pm
1 stop8h 14m
$457
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Sat 5/9
7:35 am-7:04 pm
1 stop13h 29m
San José del Cabo Los Cabos
Sat 5/16
7:47 pm-5:52 am
1 stop8h 05m
$465
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Wed 5/20
3:45 pm-10:28 pm
1 stop8h 43m
San José del Cabo Los Cabos
Wed 5/27
10:24 am-11:59 pm
2 stops11h 35m
$472
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Thu 4/30
2:15 am-7:00 pm
1 stop18h 45m
San José del Cabo Los Cabos
Sun 5/3
7:40 am-12:45 am
1 stop15h 05m
$473
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Fri 5/22
7:35 am-7:04 pm
1 stop13h 29m
San José del Cabo Los Cabos
Mon 5/25
7:47 pm-5:52 am
1 stop8h 05m
$473
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Tue 6/23
1:40 am-10:09 am
1 stop10h 29m
San José del Cabo Los Cabos
Sun 6/28
7:47 pm-5:52 am
1 stop8h 05m
$479
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Wed 7/29
10:08 am-10:30 pm
2 stops14h 22m
San José del Cabo Los Cabos
Wed 8/5
10:10 am-9:47 pm
1 stop9h 37m
$498
Showing 1-10 of 44 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
What is the cheapest month to book a flight from Chicago to Los Cabos?
Currently, June is the cheapest month in which you can book a flight from Chicago to Los Cabos (average of $365). Flying from Chicago to Los Cabos in May is currently the most expensive (average of $420). 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 10, 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 10, 2026.
The most flights from CHI to zzKPG are scheduled on a Monday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (3 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 10, 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.
Food
7.0
Entertainment
7.5
Overall
8.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Entertainment
7.5
Overall
8.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Entertainment
7.5
Overall
8.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Entertainment
7.5
Overall
8.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Entertainment
7.5
Overall
8.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Entertainment
7.5
Overall
8.0
Comfort
8.0
Crew
8.6
Boarding
8.1
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
See prices for flight routes from nearby airports that may be better suited for you.
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 10, 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 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$177 | Average$439 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$184 | Average$500 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$185 | Average$384 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$415 | Average$620 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$416 | Average$612 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$475 | Average$692 | FlexibilityNo cancel fee | On-time63% |