$107+ 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
Apr 27 — May 41
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 March 28, 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 March 28, 2026.
This Volaris deal was found by Cheapflights users on 3/24. 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.
Tue 5/57:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Sat 5/93:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 3/24![Volaris logo]()
$418
This Delta deal was found by Cheapflights users on 3/25. 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.
Sun 5/36:00 am
MDW
- SJD
1 stop9h 04m
Delta
Wed 5/612:36 pm
SJD
- MDW
1 stop7h 52m
Delta
Deal found 3/25![Delta logo]()
$418
This Volaris deal was found by Cheapflights users on 3/24. 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 10/87:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Mon 10/127:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 3/24![Volaris logo]()
$419
This Volaris deal was found by Cheapflights users on 3/27. 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 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 3/27![Volaris logo]()
$420
This Volaris deal was found by Cheapflights users on 3/24. 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.
Tue 5/192:35 am
ORD
- SJD
1 stop10h 57m
Volaris
Wed 5/277:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 3/24![Volaris logo]()
$421
This Volaris deal was found by Cheapflights users on 3/26. 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 4/101:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Sat 4/183:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 3/26![Volaris logo]()
$422
This American Airlines deal was found by Cheapflights users on 3/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/65:00 am
ORD
- SJD
1 stop7h 53m
American Airlines
Tue 5/1210:45 am
SJD
- ORD
1 stop11h 47m
American Airlines
Deal found 3/24![American Airlines logo]()
$423
This Kiwi.com deal was found by Cheapflights users on 3/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/122:35 am
ORD
- SJD
1 stop14h 19m
Volaris
Wed 5/2012:02 pm
SJD
- ORD
1 stop9h 45m
Volaris
Deal found 3/23![Volaris logo]()
$424
This lastminute.com deal was found by Cheapflights users on 3/25. 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 lastminute.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/96:23 am
MDW
- SJD
1 stop8h 27m
Aeromexico
Sat 5/166:07 am
SJD
- MDW
2 stops13h 02m
Aeromexico
Deal found 3/25![Aeromexico logo]()
$424
This American Airlines deal was found by Cheapflights users on 3/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/75:00 am
ORD
- SJD
1 stop8h 48m
American Airlines
Fri 6/1212:48 pm
SJD
- ORD
Nonstop4h 35m
American Airlines
Deal found 3/27![American Airlines logo]()
$425
This Kiwi.com deal was found by Cheapflights users on 3/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/102:35 am
ORD
- SJD
1 stop11h 50m
Multiple Airlines
Thu 5/211:05 pm
SJD
- ORD
1 stop9h 50m
Multiple Airlines
Deal found 3/23![Multiple Airlines logo]()
$426
This Kiwi.com deal was found by Cheapflights users on 3/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/111:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Mon 5/187:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 3/23![Volaris logo]()
$427
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 March 28, 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 March 28, 2026.
This Volaris deal was found by Cheapflights users on 3/26. 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.
Wed 5/277:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Sun 5/317:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 3/26![Volaris logo]()
$420
This Delta deal was found by Cheapflights users on 3/25. 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.
Sat 4/1811:19 am
ORD
- SJD
2 stops13h 09m
Delta
Fri 4/246:01 am
SJD
- ORD
2 stops12h 15m
Delta
Deal found 3/25![Delta logo]()
$445
This Viva deal was found by Cheapflights users on 3/23. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/172:15 am
ORD
- SJD
1 stop7h 45m
Viva
Sat 4/251:05 pm
SJD
- ORD
1 stop8h 40m
Viva
Deal found 3/23![Viva logo]()
$446
This United Airlines deal was found by Cheapflights users on 3/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/258:40 am
ORD
- SJD
Nonstop4h 45m
United Airlines
Sat 5/211:52 am
SJD
- ORD
Nonstop4h 17m
United Airlines
Deal found 3/26![United Airlines logo]()
$477
This Southwest deal was found by Cheapflights users on 3/27. 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 5/88:35 am
MDW
- SJD
1 stop6h 50m
Southwest
Mon 5/181:25 pm
SJD
- MDW
1 stop6h 30m
Southwest
Deal found 3/27![Southwest logo]()
$618
This Delta deal was found by Cheapflights users on 3/26. 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.
Fri 5/156:24 am
ORD
- SJD
2 stops13h 24m
Delta
Wed 5/202:41 pm
SJD
- ORD
1 stop7h 29m
Delta
Deal found 3/26![Delta logo]()
$445
This Volaris deal was found by Cheapflights users on 3/23. 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.
Tue 4/72:35 am
ORD
- SJD
1 stop10h 57m
Volaris
Tue 4/143:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 3/23![Volaris logo]()
$454
This Volaris deal was found by Cheapflights users on 3/23. 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.
Sat 4/117:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Sat 4/2512:02 pm
SJD
- ORD
1 stop9h 45m
Volaris
Deal found 3/23![Volaris logo]()
$454
This Delta deal was found by Cheapflights users on 3/26. 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.
Wed 6/33:50 pm
ORD
- SJD
1 stop8h 35m
Delta
Sun 6/76:00 am
SJD
- ORD
2 stops14h 13m
Delta
Deal found 3/26![Delta logo]()
$468
This Volaris deal was found by Cheapflights users on 3/23. 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 5/77:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Sun 5/103:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 3/23![Volaris logo]()
$459
This Delta deal was found by Cheapflights users on 3/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/83:50 pm
ORD
- SJD
1 stop8h 40m
Delta
Sat 6/1310:20 am
SJD
- ORD
1 stop11h 55m
Delta
Deal found 3/24![Delta logo]()
$482
This Volaris deal was found by Cheapflights users on 3/24. 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 6/187:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Mon 6/2212:02 pm
SJD
- ORD
1 stop9h 45m
Volaris
Deal found 3/24![Volaris logo]()
$466
This Southwest deal was found by Cheapflights users on 3/26. 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.
Tue 7/77:00 am
MDW
- SJD
2 stops8h 40m
Southwest
Tue 7/1411:35 am
SJD
- MDW
2 stops10h 30m
Southwest
Deal found 3/26![Southwest logo]()
$627
This Volaris deal was found by Cheapflights users on 3/23. 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.
Fri 4/247:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Mon 4/273:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 3/23![Volaris logo]()
$469
This Southwest deal was found by Cheapflights users on 3/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/66:10 am
MDW
- SJD
1 stop8h 05m
Southwest
Sun 9/1310:25 am
SJD
- MDW
1 stop8h 15m
Southwest
Deal found 3/25![Southwest logo]()
$632
This Southwest deal was found by Cheapflights users on 3/23. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/207:25 am
MDW
- SJD
1 stop6h 45m
Southwest
Wed 5/2712:25 pm
SJD
- MDW
1 stop8h 55m
Southwest
Deal found 3/23![Southwest logo]()
$635
This Delta deal was found by Cheapflights users on 3/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:00 am
MDW
- SJD
2 stops13h 41m
Delta
Wed 9/1612:15 pm
SJD
- MDW
1 stop7h 31m
Delta
Deal found 3/24![Delta logo]()
$587
This Southwest deal was found by Cheapflights users on 3/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/15:25 am
MDW
- SJD
1 stop7h 20m
Southwest
Mon 5/411:40 am
SJD
- MDW
1 stop10h 00m
Southwest
Deal found 3/25![Southwest logo]()
$645
This Delta deal was found by Cheapflights users on 3/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/56:00 am
MDW
- SJD
1 stop7h 31m
Delta
Sun 5/106:02 am
SJD
- MDW
2 stops13h 07m
Delta
Deal found 3/24![Delta logo]()
$621
This Southwest deal was found by Cheapflights users on 3/27. 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.
Wed 5/206:30 am
MDW
- SJD
2 stops8h 55m
Southwest
Sun 5/242:35 pm
SJD
- MDW
1 stop7h 35m
Southwest
Deal found 3/27![Southwest logo]()
$648
Last-minute flights from Chicago to Los CabosDiscover last-minute flight deals from Chicago to Los Cabos. Data last updated March 28, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Los Cabos. Data last updated March 28, 2026 and is based on user searches.
This Gotogate deal was found by Cheapflights users on 3/23. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/27:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Tue 4/77:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 3/23![Volaris logo]()
$488
This Trip.com deal was found by Cheapflights users on 3/27. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/21:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Tue 4/77:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 3/27![Volaris logo]()
$517
This Trip.com deal was found by Cheapflights users on 3/26. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/47:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Tue 4/77:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 3/26![Volaris logo]()
$472
This Kiwi.com deal was found by Cheapflights users on 3/24. 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.
Sat 4/42:35 am
ORD
- SJD
1 stop10h 57m
Volaris
Wed 4/157:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 3/24![Volaris logo]()
$492
This Kiwi.com deal was found by Cheapflights users on 3/24. 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.
Sat 4/42:35 am
ORD
- SJD
1 stop10h 57m
Volaris
Tue 4/147:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 3/24![Volaris logo]()
$518
This Trip.com deal was found by Cheapflights users on 3/26. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/57:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Thu 4/912:02 pm
SJD
- ORD
1 stop9h 45m
Volaris
Deal found 3/26![Volaris logo]()
$467
This Kiwi.com deal was found by Cheapflights users on 3/24. 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 4/62:15 am
ORD
- SJD
2 stops9h 54m
Multiple Airlines
Wed 4/157:47 pm
SJD
- ORD
1 stop8h 05m
Multiple Airlines
Deal found 3/24![Multiple Airlines logo]()
$486
This Kiwi.com deal was found by Cheapflights users on 3/24. 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 4/62:15 am
ORD
- SJD
2 stops9h 54m
Multiple Airlines
Tue 4/147:47 pm
SJD
- ORD
1 stop8h 05m
Multiple Airlines
Deal found 3/24![Multiple Airlines logo]()
$516
This Trip.com deal was found by Cheapflights users on 3/24. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/77:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Fri 4/107:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 3/24![Volaris logo]()
$514
This Southwest deal was found by Cheapflights users on 3/24. 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 4/205:30 am
MDW
- SJD
2 stops8h 40m
Southwest
Sat 5/3012:40 pm
SJD
- MDW
1 stop13h 55m
Southwest
Deal found 3/24![Southwest logo]()
$547
This Delta deal was found by Cheapflights users on 3/25. 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 4/2412:52 pm
MDW
- SJD
2 stops11h 38m
Delta
Fri 5/112:36 pm
SJD
- MDW
1 stop7h 52m
Delta
Deal found 3/25![Delta logo]()
$445
This Delta deal was found by Cheapflights users on 3/26. 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 4/256:00 am
MDW
- SJD
2 stops13h 49m
Delta
Sat 5/212:36 pm
SJD
- MDW
1 stop7h 52m
Delta
Deal found 3/26![Delta logo]()
$472
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 March 28, 2026.
Search for one-way flight options from Chicago to Los Cabos. Find affordable one-way fares based on user searches. Data last updated March 28, 2026.
This Trip.com deal was found by Cheapflights users on 3/27. 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 Trip.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 3/27![Volaris logo]()
$107
This Kiwi.com deal was found by Cheapflights users on 3/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/261:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Deal found 3/23![Volaris logo]()
$109
This Super.com deal was found by Cheapflights users on 3/25. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/241:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Deal found 3/25![Volaris logo]()
$112
This Super.com deal was found by Cheapflights users on 3/25. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/291:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Deal found 3/25![Volaris logo]()
$114
This Super.com deal was found by Cheapflights users on 3/25. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/257:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Deal found 3/25![Volaris logo]()
$117
This Trip.com deal was found by Cheapflights users on 3/27. 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 Trip.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 3/27![Volaris logo]()
$121
This Trip.com deal was found by Cheapflights users on 3/27. 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 Trip.com 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
Deal found 3/27![Volaris logo]()
$125
This Super.com deal was found by Cheapflights users on 3/25. 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 Super.com 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
Deal found 3/25![Volaris logo]()
$127
This Super.com deal was found by Cheapflights users on 3/25. 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 Super.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 stop10h 36m
Volaris
Deal found 3/25![Volaris logo]()
$128
This Super.com deal was found by Cheapflights users on 3/25. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/259:53 pm
MDW
- SJD
1 stop11h 38m
Volaris
Deal found 3/25![Volaris logo]()
$150
This Delta deal was found by Cheapflights users on 3/26. 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.
Sun 4/266:00 am
MDW
- SJD
2 stops13h 49m
Delta
Deal found 3/26![Delta logo]()
$187
This Volaris deal was found by Cheapflights users on 3/27. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/279:53 pm
MDW
- SJD
1 stop11h 38m
Volaris
Deal found 3/27![Volaris logo]()
$188
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 March 28, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $418 (Volaris) |
One-way from | $107 (Trip.com) |
Popular in | March |
Cheapest in | September |
Average price | $726 |
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 March 28, 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
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
$420
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Sat 4/18
11:19 am-10:28 pm
2 stops13h 09m
San José del Cabo Los Cabos
Fri 4/24
6:01 am-8:16 pm
2 stops12h 15m
$445
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Fri 5/15
6:24 am-5:48 pm
2 stops13h 24m
San José del Cabo Los Cabos
Wed 5/20
2:41 pm-12:10 am
1 stop7h 29m
$445
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Fri 4/17
2:15 am-8:00 am
1 stop7h 45m
San José del Cabo Los Cabos
Sat 4/25
1:05 pm-11:45 pm
1 stop8h 40m
$446
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Tue 4/7
2:35 am-11:32 am
1 stop10h 57m
San José del Cabo Los Cabos
Tue 4/14
3:36 pm-12:55 am
1 stop7h 19m
$454
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Sat 4/11
7:35 am-7:04 pm
1 stop13h 29m
San José del Cabo Los Cabos
Sat 4/25
12:02 pm-11:47 pm
1 stop9h 45m
$454
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Thu 5/7
7:35 am-7:04 pm
1 stop13h 29m
San José del Cabo Los Cabos
Sun 5/10
3:36 pm-12:55 am
1 stop7h 19m
$459
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
12:02 pm-11:47 pm
1 stop9h 45m
$466
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Wed 6/3
3:50 pm-10:25 pm
1 stop8h 35m
San José del Cabo Los Cabos
Sun 6/7
6:00 am-10:13 pm
2 stops14h 13m
$468
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Fri 4/24
7:35 am-7:04 pm
1 stop13h 29m
San José del Cabo Los Cabos
Mon 4/27
3:36 pm-12:55 am
1 stop7h 19m
$469
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
What is the cheapest month to book a flight from Chicago to Los Cabos?
Currently, April is the cheapest month in which you can book a flight from Chicago to Los Cabos (average of $315). Flying from Chicago to Los Cabos in February is currently the most expensive (average of $417). 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 March 28, 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 March 28, 2026.
The most flights from CHI to zzKPG are scheduled on a Thursday (6 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 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 March 28, 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.
Food
7.0
Entertainment
7.5
Comfort
8.0
Overall
8.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Entertainment
7.5
Comfort
8.0
Overall
8.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Entertainment
7.5
Comfort
8.0
Overall
8.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Entertainment
7.5
Comfort
8.0
Overall
8.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Entertainment
7.5
Comfort
8.0
Overall
8.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Entertainment
7.5
Comfort
8.0
Overall
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
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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 March 28, 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 March 28, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$177 | Average$376 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$184 | Average$500 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$185 | Average$386 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$415 | Average$618 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$416 | Average$612 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$475 | Average$655 | FlexibilityNo cancel fee | On-time63% |