$111+ 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 7/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJD
Jul 10 — Jul 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 June 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 June 10, 2026.
This FlightHub deal was found by Cheapflights users on 6/7. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/297:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Fri 7/312:02 pm
SJD
- ORD
1 stop9h 45m
Volaris
Deal found 6/7![Volaris logo]()
$384
This Kiwi.com deal was found by Cheapflights users on 6/8. 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 7/72:53 am
ORD
- SJD
1 stop10h 36m
Volaris
Mon 7/133:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 6/8![Volaris logo]()
$385
This FlightHub deal was found by Cheapflights users on 6/8. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/117:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Tue 6/1612:02 pm
SJD
- ORD
1 stop9h 45m
Volaris
Deal found 6/8![Volaris logo]()
$386
This FlightHub deal was found by Cheapflights users on 6/8. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/102:53 am
ORD
- SJD
1 stop7h 23m
Volaris
Sat 7/183:36 pm
SJD
- ORD
1 stop11h 05m
Volaris
Deal found 6/8![Volaris logo]()
$387
This Kiwi.com deal was found by Cheapflights users on 6/8. 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 7/91:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Sat 7/113:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 6/8![Volaris logo]()
$388
This Kiwi.com deal was found by Cheapflights users on 6/8. 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 7/62:53 am
ORD
- SJD
1 stop10h 36m
Volaris
Fri 7/103:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 6/8![Volaris logo]()
$389
This Kiwi.com deal was found by Cheapflights users on 6/9. 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.
Sat 9/127:35 am
ORD
- SJD
1 stop13h 29m
Multiple Airlines
Sat 9/198:05 am
SJD
- ORD
2 stops14h 50m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$390
This Kiwi.com deal was found by Cheapflights users on 6/8. 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 7/82:53 am
ORD
- SJD
1 stop7h 23m
Volaris
Mon 7/133:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 6/8![Volaris logo]()
$391
This Volaris deal was found by Cheapflights users on 6/10. 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.
Sun 10/257:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Sat 10/317:47 pm
SJD
- ORD
1 stop7h 49m
Volaris
Deal found 6/10![Volaris logo]()
$392
This Kiwi.com deal was found by Cheapflights users on 6/9. 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.
Thu 12/36:23 am
ORD
- SJD
1 stop10h 12m
Volaris
Fri 12/113:36 pm
SJD
- ORD
1 stop7h 03m
Volaris
Deal found 6/9![Volaris logo]()
$393
This FlightHub deal was found by Cheapflights users on 6/8. 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 FlightHub 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 6/8![Volaris logo]()
$394
This Kiwi.com deal was found by Cheapflights users on 6/8. 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 7/21:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Sun 7/53:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 6/8![Volaris logo]()
$395
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 June 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 June 10, 2026.
This Viva deal was found by Cheapflights users on 6/10. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/612:30 am
ORD
- SJD
1 stop8h 05m
Viva
Sat 12/121:10 pm
SJD
- ORD
1 stop8h 47m
Viva
Deal found 6/10![Viva logo]()
$397
This Volaris deal was found by Cheapflights users on 6/5. 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.
Tue 6/301:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Wed 7/812:02 pm
SJD
- ORD
1 stop9h 45m
Volaris
Deal found 6/5![Volaris logo]()
$443
This Delta deal was found by Cheapflights users on 6/9. 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 11/295:30 am
ORD
- SJD
1 stop7h 55m
Delta
Thu 12/1010:25 am
SJD
- ORD
1 stop11h 35m
Delta
Deal found 6/9![Delta logo]()
$470
This Southwest deal was found by Cheapflights users on 6/9. 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.
Mon 8/105:30 am
MDW
- SJD
2 stops9h 20m
Southwest
Fri 8/1410:40 am
SJD
- MDW
2 stops10h 40m
Southwest
Deal found 6/9![Southwest logo]()
$493
This United Airlines deal was found by Cheapflights users on 6/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/149:30 pm
ORD
- SJD
1 stop16h 40m
United Airlines
Tue 11/1712:50 pm
SJD
- ORD
Nonstop4h 13m
United Airlines
Deal found 6/9![United Airlines logo]()
$530
This Alaska Airlines deal was found by Cheapflights users on 6/8. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/122:18 pm
ORD
- SJD
2 stops21h 53m
Alaska Airlines
Sat 9/197:02 pm
SJD
- ORD
2 stops22h 19m
Alaska Airlines
Deal found 6/8![Alaska Airlines logo]()
$570
This Volaris deal was found by Cheapflights users on 6/7. 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 12/16:23 am
ORD
- SJD
1 stop10h 12m
Volaris
Tue 12/153:36 pm
SJD
- ORD
1 stop7h 03m
Volaris
Deal found 6/7![Volaris logo]()
$470
This Delta deal was found by Cheapflights users on 6/9. 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.
Mon 9/146:05 am
MDW
- SJD
2 stops13h 20m
Delta
Fri 9/186:15 am
SJD
- MDW
2 stops14h 10m
Delta
Deal found 6/9![Delta logo]()
$480
This Alaska Airlines deal was found by Cheapflights users on 6/6. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/282:17 pm
ORD
- SJD
1 stop26h 33m
Alaska Airlines
Wed 11/45:03 pm
SJD
- ORD
2 stops19h 20m
Alaska Airlines
Deal found 6/6![Alaska Airlines logo]()
$580
This Volaris deal was found by Cheapflights users on 6/9. 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.
Wed 7/11:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Sun 7/57:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 6/9![Volaris logo]()
$539
This Alaska Airlines deal was found by Cheapflights users on 6/5. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/276:20 am
ORD
- SJD
1 stop10h 19m
Alaska Airlines
Fri 7/310:45 am
SJD
- ORD
1 stop10h 51m
Alaska Airlines
Deal found 6/5![Alaska Airlines logo]()
$589
This Southwest deal was found by Cheapflights users on 6/9. 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.
Mon 7/135:45 am
MDW
- SJD
2 stops9h 55m
Southwest
Wed 7/1510:40 am
SJD
- MDW
1 stop8h 05m
Southwest
Deal found 6/9![Southwest logo]()
$648
This Volaris deal was found by Cheapflights users on 6/7. 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 7/87:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Sat 7/113:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 6/7![Volaris logo]()
$549
This Southwest deal was found by Cheapflights users on 6/9. 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.
Mon 7/205:45 am
MDW
- SJD
2 stops9h 55m
Southwest
Fri 7/319:45 am
SJD
- MDW
2 stops10h 15m
Southwest
Deal found 6/9![Southwest logo]()
$648
This Delta deal was found by Cheapflights users on 6/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/146:05 am
MDW
- SJD
2 stops13h 20m
Delta
Sat 9/1912:15 pm
SJD
- MDW
1 stop8h 10m
Delta
Deal found 6/6![Delta logo]()
$669
This Volaris deal was found by Cheapflights users on 6/8. 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.
Tue 6/232:53 am
ORD
- SJD
1 stop10h 36m
Volaris
Sun 6/2812:02 pm
SJD
- ORD
1 stop9h 45m
Volaris
Deal found 6/8![Volaris logo]()
$567
This Southwest deal was found by Cheapflights users on 6/9. 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 7/35:15 am
MDW
- SJD
1 stop9h 05m
Southwest
Fri 7/102:35 pm
SJD
- MDW
1 stop8h 05m
Southwest
Deal found 6/9![Southwest logo]()
$669
This Delta deal was found by Cheapflights users on 6/5. 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 7/296:00 am
MDW
- SJD
2 stops14h 40m
Delta
Sun 8/212:16 pm
SJD
- MDW
1 stop8h 00m
Delta
Deal found 6/5![Delta logo]()
$679
This Volaris deal was found by Cheapflights users on 6/7. 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.
Thu 11/126:23 am
ORD
- SJD
1 stop10h 12m
Volaris
Mon 11/163:36 pm
SJD
- ORD
1 stop7h 03m
Volaris
Deal found 6/7![Volaris logo]()
$577
This Southwest deal was found by Cheapflights users on 6/6. 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.
Mon 9/145:15 am
MDW
- SJD
2 stops9h 35m
Southwest
Sat 9/192:05 pm
SJD
- MDW
1 stop13h 35m
Southwest
Deal found 6/6![Southwest logo]()
$673
This Delta deal was found by Cheapflights users on 6/7. 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 9/126:00 am
MDW
- SJD
1 stop7h 10m
Delta
Sat 9/1912:15 pm
SJD
- MDW
1 stop8h 10m
Delta
Deal found 6/7![Delta logo]()
$694
This Southwest deal was found by Cheapflights users on 6/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/105:10 am
MDW
- SJD
2 stops10h 15m
Southwest
Wed 7/1511:35 am
SJD
- MDW
2 stops10h 35m
Southwest
Deal found 6/8![Southwest logo]()
$673
This Southwest deal was found by Cheapflights users on 6/5. 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.
Wed 7/297:00 am
MDW
- SJD
1 stop9h 15m
Southwest
Sun 8/211:05 am
SJD
- MDW
2 stops10h 35m
Southwest
Deal found 6/5![Southwest logo]()
$683
Last-minute flights from Chicago to Los CabosDiscover last-minute flight deals from Chicago to Los Cabos. Data last updated June 10, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Los Cabos. Data last updated June 10, 2026 and is based on user searches.
This FlightHub deal was found by Cheapflights users on 6/8. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/117:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Tue 6/1612:02 pm
SJD
- ORD
1 stop9h 45m
Volaris
Deal found 6/8![Volaris logo]()
$386
This Super.com deal was found by Cheapflights users on 6/7. 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 Super.com 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
Sun 6/217:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 6/7![Volaris logo]()
$393
This FlightHub deal was found by Cheapflights users on 6/8. 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 FlightHub 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 6/8![Volaris logo]()
$394
This FlightHub deal was found by Cheapflights users on 6/7. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/297:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Fri 7/312:02 pm
SJD
- ORD
1 stop9h 45m
Volaris
Deal found 6/7![Volaris logo]()
$384
This Super.com deal was found by Cheapflights users on 6/9. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/36:21 am
ORD
- SJD
1 stop10h 30m
Volaris
Sun 7/57:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 6/9![Volaris logo]()
$390
This Kiwi.com deal was found by Cheapflights users on 6/8. 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 7/62:53 am
ORD
- SJD
1 stop10h 36m
Volaris
Fri 7/103:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 6/8![Volaris logo]()
$389
This Kiwi.com deal was found by Cheapflights users on 6/8. 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 7/72:53 am
ORD
- SJD
1 stop10h 36m
Volaris
Mon 7/133:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 6/8![Volaris logo]()
$385
This Kiwi.com deal was found by Cheapflights users on 6/8. 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 7/82:53 am
ORD
- SJD
1 stop7h 23m
Volaris
Mon 7/133:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 6/8![Volaris logo]()
$391
This Kiwi.com deal was found by Cheapflights users on 6/8. 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 7/91:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Sat 7/113:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 6/8![Volaris logo]()
$388
This FlightHub deal was found by Cheapflights users on 6/8. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/102:53 am
ORD
- SJD
1 stop7h 23m
Volaris
Sat 7/183:36 pm
SJD
- ORD
1 stop11h 05m
Volaris
Deal found 6/8![Volaris logo]()
$387
This Super.com deal was found by Cheapflights users on 6/8. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/168:49 pm
MDW
- SJD
1 stop13h 27m
Volaris
Mon 7/208:50 am
SJD
- MDW
1 stop8h 14m
Volaris
Deal found 6/8![Volaris logo]()
$482
This Kiwi.com deal was found by Cheapflights users on 6/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/228:23 pm
MDW
- SJD
1 stop13h 53m
Multiple Airlines
Mon 7/277:47 pm
SJD
- MDW
2 stops19h 04m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$618
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 June 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 June 10, 2026.
This Super.com deal was found by Cheapflights users on 6/7. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/126:21 am
ORD
- SJD
1 stop10h 30m
Volaris
Deal found 6/7![Volaris logo]()
$111
This Super.com deal was found by Cheapflights users on 6/10. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/77:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Deal found 6/10![Volaris logo]()
$116
This Kiwi.com deal was found by Cheapflights users on 6/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/301:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Deal found 6/6![Volaris logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 6/10. 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.
Fri 7/106:21 am
ORD
- SJD
1 stop10h 30m
Volaris
Deal found 6/10![Volaris logo]()
$118
This CheapOair deal was found by Cheapflights users on 6/5. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Deal found 6/5![Volaris logo]()
$119
This Super.com deal was found by Cheapflights users on 6/10. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/257:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Deal found 6/10![Volaris logo]()
$122
This Kiwi.com deal was found by Cheapflights users on 6/9. 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.
Wed 7/81:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Deal found 6/9![Volaris logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 6/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/301:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Deal found 6/6![Volaris logo]()
$124
This Kiwi.com deal was found by Cheapflights users on 6/5. 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.
Sun 7/56:21 am
ORD
- SJD
1 stop7h 08m
Volaris
Deal found 6/5![Volaris logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 6/10. 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.
Tue 9/87:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Deal found 6/10![Volaris logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 6/9. 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 7/62:53 am
ORD
- SJD
1 stop10h 36m
Volaris
Deal found 6/9![Volaris logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 6/9. 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.
Sun 7/51:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Deal found 6/9![Volaris logo]()
$128
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 June 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $384 (FlightHub) |
One-way from | $111 (Super.com) |
Popular in | March |
Cheapest in | September |
Average price | $603 |
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 June 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
Sun 12/6
12:30 am-7:35 am
1 stop8h 05m
San José del Cabo Los Cabos
Sat 12/12
1:10 pm-10:57 pm
1 stop8h 47m
$397
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Tue 6/30
1:40 am-10:09 am
1 stop10h 29m
San José del Cabo Los Cabos
Wed 7/8
12:02 pm-11:47 pm
1 stop9h 45m
$443
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Sun 11/29
5:30 am-12:25 pm
1 stop7h 55m
San José del Cabo Los Cabos
Thu 12/10
10:25 am-11:00 pm
1 stop11h 35m
$470
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Tue 12/1
6:23 am-3:35 pm
1 stop10h 12m
San José del Cabo Los Cabos
Tue 12/15
3:36 pm-11:39 pm
1 stop7h 03m
$470
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Mon 9/14
6:05 am-5:25 pm
2 stops13h 20m
San José del Cabo Los Cabos
Fri 9/18
6:15 am-10:25 pm
2 stops14h 10m
$480
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Mon 8/10
5:30 am-12:50 pm
2 stops9h 20m
San José del Cabo Los Cabos
Fri 8/14
10:40 am-11:20 pm
2 stops10h 40m
$493
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Sat 11/14
9:30 pm-1:10 pm
1 stop16h 40m
San José del Cabo Los Cabos
Tue 11/17
12:50 pm-6:03 pm
Nonstop4h 13m
$530
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Wed 7/1
1:40 am-10:09 am
1 stop10h 29m
San José del Cabo Los Cabos
Sun 7/5
7:47 pm-5:52 am
1 stop8h 05m
$539
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Wed 7/8
7:35 am-7:04 pm
1 stop13h 29m
San José del Cabo Los Cabos
Sat 7/11
3:36 pm-12:55 am
1 stop7h 19m
$549
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Tue 6/23
2:53 am-11:29 am
1 stop10h 36m
San José del Cabo Los Cabos
Sun 6/28
12:02 pm-11:47 pm
1 stop9h 45m
$567
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, 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 $1,121). 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 June 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 June 10, 2026.
The most flights from CHI to zzKPG are scheduled on a Monday (1 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).
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 16 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.
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 June 10, 2026.
Peruse reviews from past customers who have flown with Southwest,United Airlines, andAmerican 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
Food
7.0
Boarding
8.1
Overall
7.9
Crew
8.6
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Entertainment
7.5
Food
7.0
Boarding
8.1
Overall
7.9
Crew
8.6
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Entertainment
7.5
Food
7.0
Boarding
8.1
Overall
7.9
Crew
8.6
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Entertainment
7.5
Food
7.0
Boarding
8.1
Overall
7.9
Crew
8.6
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Entertainment
7.5
Food
7.0
Boarding
8.1
Overall
7.9
Crew
8.6
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Entertainment
7.5
Food
7.0
Boarding
8.1
Overall
7.9
Crew
8.6
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
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 June 10, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 5 airlines flying from Chicago to Los Cabos
Discover the top 5 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 June 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$185 | Average$391 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$223 | Average$470 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$417 | Average$640 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$417 | Average$633 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$475 | Average$695 | FlexibilityNo cancel fee | On-time63% |