$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 4/26. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJD
Mar 28 — Apr 41
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
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
Cheapest
Best
Last-minute
One-way
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 February 26, 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 February 26, 2026.
This Mytrip deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/121:40 am
ORD
- SJD
2 stops15h 11m
Volaris
Sat 4/184:49 pm
SJD
- ORD
2 stops17h 20m
Volaris
Deal found 2/22![Volaris logo]()
$459
This Kiwi.com deal was found by Cheapflights users on 2/24. 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 2/2812:59 pm
ORD
- SJD
1 stop19h 01m
Multiple Airlines
Mon 3/24:34 pm
SJD
- ORD
2 stops17h 45m
Multiple Airlines
Deal found 2/24![Multiple Airlines logo]()
$460
This Mytrip deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/111:58 pm
ORD
- SJD
2 stops11h 38m
Volaris
Thu 3/512:59 pm
SJD
- ORD
2 stops21h 20m
Volaris
Deal found 2/22![Volaris logo]()
$461
This Alaska Airlines deal was found by Cheapflights users on 2/23. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/56:00 am
ORD
- SJD
1 stop10h 37m
Alaska Airlines
Sun 5/1012:54 pm
SJD
- ORD
2 stops22h 19m
Alaska Airlines
Deal found 2/23![Alaska Airlines logo]()
$462
This Southwest deal was found by Cheapflights users on 2/23. 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.
Mon 5/258:35 am
MDW
- SJD
1 stop6h 50m
Southwest
Thu 5/281:55 pm
SJD
- MDW
1 stop12h 40m
Southwest
Deal found 2/23![Southwest logo]()
$462
This Aeromexico deal was found by Cheapflights users on 2/25. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/52:00 am
ORD
- SJD
1 stop17h 50m
Aeromexico
Sun 5/106:40 pm
SJD
- ORD
2 stops21h 55m
Aeromexico
Deal found 2/25![Aeromexico logo]()
$463
This Aeromexico deal was found by Cheapflights users on 2/26. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/262:00 am
ORD
- SJD
1 stop13h 45m
Aeromexico
Sun 5/316:00 am
SJD
- ORD
1 stop16h 15m
Aeromexico
Deal found 2/26![Aeromexico logo]()
$464
This Alaska Airlines deal was found by Cheapflights users on 2/25. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/17:59 pm
ORD
- SJD
1 stop17h 45m
Alaska Airlines
Mon 5/410:41 am
SJD
- ORD
1 stop11h 02m
Alaska Airlines
Deal found 2/25![Alaska Airlines logo]()
$465
This Kiwi.com deal was found by Cheapflights users on 2/23. 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.
Thu 4/235:20 am
ORD
- SJD
2 stops35h 31m
Multiple Airlines
Mon 4/271:05 pm
SJD
- ORD
1 stop9h 34m
Multiple Airlines
Deal found 2/23![Multiple Airlines logo]()
$466
This Aeromexico deal was found by Cheapflights users on 2/25. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/25:59 pm
ORD
- SJD
2 stops21h 46m
Aeromexico
Sat 5/910:20 am
SJD
- ORD
2 stops11h 39m
Aeromexico
Deal found 2/25![Aeromexico logo]()
$467
This Aeromexico deal was found by Cheapflights users on 2/23. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/36:00 am
MDW
- SJD
1 stop7h 31m
Aeromexico
Sun 5/106:40 pm
SJD
- MDW
2 stops19h 32m
Aeromexico
Deal found 2/23![Aeromexico logo]()
$467
This American Airlines deal was found by Cheapflights users on 2/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/510:05 am
ORD
- SJD
Nonstop4h 45m
American Airlines
Sun 5/104:25 pm
SJD
- ORD
1 stop13h 06m
American Airlines
Deal found 2/26![American Airlines logo]()
$468
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 February 26, 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 February 26, 2026.
This Alaska Airlines deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/114:10 pm
ORD
- SJD
1 stop24h 38m
Alaska Airlines
Fri 4/172:30 pm
SJD
- ORD
2 stops21h 51m
Alaska Airlines
Deal found 2/22![Alaska Airlines logo]()
$486
This United Airlines deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/138:40 am
ORD
- SJD
Nonstop4h 45m
United Airlines
Sat 4/1811:52 am
SJD
- ORD
Nonstop4h 17m
United Airlines
Deal found 2/22![United Airlines logo]()
$515
This Delta deal was found by Cheapflights users on 2/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/195:30 am
ORD
- SJD
2 stops14h 13m
Delta
Thu 3/2612:35 pm
SJD
- ORD
1 stop9h 19m
Delta
Deal found 2/23![Delta logo]()
$529
This Southwest deal was found by Cheapflights users on 2/25. 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.
Sat 4/115:10 am
MDW
- SJD
1 stop7h 30m
Southwest
Sat 4/181:55 pm
SJD
- MDW
1 stop6h 50m
Southwest
Deal found 2/25![Southwest logo]()
$534
This United Airlines deal was found by Cheapflights users on 2/24. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/267:15 am
ORD
- SJD
Nonstop4h 53m
United Airlines
Thu 4/21:17 pm
SJD
- ORD
1 stop9h 13m
United Airlines
Deal found 2/24![United Airlines logo]()
$525
This Delta deal was found by Cheapflights users on 2/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/115:59 pm
ORD
- SJD
2 stops15h 41m
Delta
Sat 4/1810:20 am
SJD
- ORD
2 stops11h 39m
Delta
Deal found 2/23![Delta logo]()
$534
This Southwest deal was found by Cheapflights users on 2/23. 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 4/157:30 am
MDW
- SJD
1 stop7h 55m
Southwest
Mon 4/201:55 pm
SJD
- MDW
1 stop12h 40m
Southwest
Deal found 2/23![Southwest logo]()
$583
This Alaska Airlines deal was found by Cheapflights users on 2/24. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/282:20 pm
ORD
- SJD
2 stops21h 59m
Alaska Airlines
Fri 7/310:45 am
SJD
- ORD
1 stop10h 54m
Alaska Airlines
Deal found 2/24![Alaska Airlines logo]()
$597
This Delta deal was found by Cheapflights users on 2/24. 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 5/156:24 am
ORD
- SJD
2 stops13h 26m
Delta
Wed 5/2010:25 am
SJD
- ORD
2 stops11h 34m
Delta
Deal found 2/24![Delta logo]()
$547
This United Airlines deal was found by Cheapflights users on 2/24. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/157:00 am
ORD
- SJD
1 stop8h 43m
United Airlines
Mon 4/2011:52 am
SJD
- ORD
Nonstop4h 17m
United Airlines
Deal found 2/24![United Airlines logo]()
$547
This United Airlines deal was found by Cheapflights users on 2/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/267:15 am
ORD
- SJD
Nonstop4h 53m
United Airlines
Mon 3/3011:32 am
SJD
- ORD
1 stop11h 13m
United Airlines
Deal found 2/25![United Airlines logo]()
$551
This Delta deal was found by Cheapflights users on 2/24. 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 3/3112:47 pm
MDW
- SJD
2 stops20h 53m
Delta
Sat 4/48:35 am
SJD
- MDW
2 stops11h 56m
Delta
Deal found 2/24![Delta logo]()
$563
This Southwest deal was found by Cheapflights users on 2/23. 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 5/137:25 am
MDW
- SJD
1 stop6h 45m
Southwest
Sun 5/1712:40 pm
SJD
- MDW
1 stop13h 55m
Southwest
Deal found 2/23![Southwest logo]()
$675
This Delta deal was found by Cheapflights users on 2/24. 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.
Wed 4/16:00 am
MDW
- SJD
1 stop7h 30m
Delta
Sat 4/48:35 am
SJD
- MDW
2 stops11h 56m
Delta
Deal found 2/24![Delta logo]()
$563
This United Airlines deal was found by Cheapflights users on 2/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/165:40 am
ORD
- SJD
1 stop7h 03m
United Airlines
Thu 3/1911:50 am
SJD
- ORD
Nonstop4h 09m
United Airlines
Deal found 2/25![United Airlines logo]()
$598
This Southwest deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/206:05 am
MDW
- SJD
1 stop8h 15m
Southwest
Tue 3/241:50 pm
SJD
- MDW
2 stops13h 30m
Southwest
Deal found 2/22![Southwest logo]()
$684
This Delta deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/76:00 am
ORD
- SJD
2 stops13h 50m
Delta
Wed 5/1310:25 am
SJD
- ORD
2 stops11h 34m
Delta
Deal found 2/22![Delta logo]()
$602
This Southwest deal was found by Cheapflights users on 2/24. 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.
Sun 4/55:00 am
MDW
- SJD
2 stops9h 00m
Southwest
Fri 4/1010:45 am
SJD
- MDW
1 stop9h 10m
Southwest
Deal found 2/24![Southwest logo]()
$689
This Southwest deal was found by Cheapflights users on 2/24. 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.
Wed 3/1810:40 am
MDW
- SJD
Nonstop4h 55m
Southwest
Fri 3/2011:55 am
SJD
- MDW
Nonstop4h 00m
Southwest
Deal found 2/24![Southwest logo]()
$786
This Delta deal was found by Cheapflights users on 2/25. 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.
Tue 5/512:52 pm
MDW
- SJD
2 stops11h 33m
Delta
Sun 5/106:00 am
SJD
- MDW
2 stops13h 09m
Delta
Deal found 2/25![Delta logo]()
$742
This Southwest deal was found by Cheapflights users on 2/24. 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.
Thu 4/306:00 am
MDW
- SJD
2 stops9h 25m
Southwest
Sun 5/33:05 pm
SJD
- MDW
1 stop12h 40m
Southwest
Deal found 2/24![Southwest logo]()
$794
This Southwest deal was found by Cheapflights users on 2/25. 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 3/159:30 am
MDW
- SJD
Nonstop4h 55m
Southwest
Fri 3/203:20 pm
SJD
- MDW
1 stop12h 25m
Southwest
Deal found 2/25![Southwest logo]()
$798
Last-minute flights from Chicago to Los CabosDiscover last-minute flight deals from Chicago to Los Cabos. Data last updated February 26, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Los Cabos. Data last updated February 26, 2026 and is based on user searches.
This Booking.com deal was found by Cheapflights users on 2/23. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/271:20 am
ORD
- SJD
1 stop7h 40m
Viva
Sat 3/711:20 am
SJD
- ORD
1 stop10h 25m
Viva
Deal found 2/23![Viva logo]()
$463
This Mytrip deal was found by Cheapflights users on 2/24. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/271:20 am
ORD
- SJD
1 stop7h 40m
Multiple Airlines
Sat 3/78:20 pm
SJD
- ORD
2 stops23h 50m
Multiple Airlines
Deal found 2/24![Multiple Airlines logo]()
$472
This Kiwi.com deal was found by Cheapflights users on 2/24. 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 2/2812:59 pm
ORD
- SJD
1 stop19h 01m
Multiple Airlines
Mon 3/24:34 pm
SJD
- ORD
2 stops17h 45m
Multiple Airlines
Deal found 2/24![Multiple Airlines logo]()
$460
This Mytrip deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/111:58 pm
ORD
- SJD
2 stops11h 38m
Volaris
Thu 3/512:59 pm
SJD
- ORD
2 stops21h 20m
Volaris
Deal found 2/22![Volaris logo]()
$461
This Mytrip deal was found by Cheapflights users on 2/25. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/112:59 pm
ORD
- SJD
2 stops24h 15m
Volaris
Sat 3/73:59 pm
SJD
- ORD
2 stops17h 20m
Volaris
Deal found 2/25![Volaris logo]()
$462
This Mytrip deal was found by Cheapflights users on 2/24. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/211:58 pm
ORD
- SJD
3 stops15h 54m
Volaris
Tue 3/36:47 pm
SJD
- ORD
2 stops15h 32m
Volaris
Deal found 2/24![Volaris logo]()
$466
This Kiwi.com deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/512:15 am
ORD
- SJD
2 stops11h 21m
Multiple Airlines
Fri 3/137:40 am
SJD
- ORD
1 stop14h 05m
Multiple Airlines
Deal found 2/25![Multiple Airlines logo]()
$465
This Kiwi.com deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/512:15 am
ORD
- SJD
1 stop7h 45m
Multiple Airlines
Sat 3/145:47 pm
SJD
- ORD
2 stops15h 32m
Multiple Airlines
Deal found 2/25![Multiple Airlines logo]()
$467
This Kiwi.com deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/512:15 am
ORD
- SJD
1 stop7h 45m
Viva
Sun 3/1510:05 pm
SJD
- ORD
1 stop24h 40m
Viva
Deal found 2/25![Viva logo]()
$470
This Mytrip deal was found by Cheapflights users on 2/23. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/66:54 pm
MDW
- SJD
1 stop17h 36m
Volaris
Fri 3/132:59 pm
SJD
- MDW
2 stops25h 35m
Volaris
Deal found 2/23![Volaris logo]()
$570
This Mytrip deal was found by Cheapflights users on 2/24. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1212:59 pm
ORD
- SJD
2 stops24h 15m
Volaris
Wed 3/184:08 pm
SJD
- ORD
1 stop11h 28m
Volaris
Deal found 2/24![Volaris logo]()
$468
This Mytrip deal was found by Cheapflights users on 2/25. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/157:23 am
ORD
- SJD
1 stop9h 57m
Multiple Airlines
Fri 3/202:59 pm
SJD
- ORD
3 stops21h 17m
Multiple Airlines
Deal found 2/25![Multiple Airlines logo]()
$471
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 February 26, 2026.
Search for one-way flight options from Chicago to Los Cabos. Find affordable one-way fares based on user searches. Data last updated February 26, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/261:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Deal found 2/26![Volaris logo]()
$94
This Booking.com deal was found by Cheapflights users on 2/25. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/311:30 am
ORD
- SJD
1 stop19h 35m
Viva
Deal found 2/25![Viva logo]()
$106
This Booking.com deal was found by Cheapflights users on 2/23. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/111:30 am
ORD
- SJD
1 stop19h 35m
Viva
Deal found 2/23![Viva logo]()
$110
This Mytrip deal was found by Cheapflights users on 2/23. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/127:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Deal found 2/23![Volaris logo]()
$111
This Mytrip deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/207:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Deal found 2/26![Volaris logo]()
$112
This Gotogate deal was found by Cheapflights users on 2/26. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/27:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Deal found 2/26![Volaris logo]()
$120
This Cheapflightsfares deal was found by Cheapflights users on 2/25. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/17:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Deal found 2/25![Volaris logo]()
$122
This Booking.com deal was found by Cheapflights users on 2/23. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/41:30 am
ORD
- SJD
1 stop19h 35m
Viva
Deal found 2/23![Viva logo]()
$123
This Gotogate deal was found by Cheapflights users on 2/26. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/201:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Deal found 2/26![Volaris logo]()
$124
This Gotogate deal was found by Cheapflights users on 2/25. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/272:19 am
ORD
- SJD
1 stop11h 10m
Volaris
Deal found 2/25![Volaris logo]()
$125
This Cheapflightsfares deal was found by Cheapflights users on 2/24. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/202:19 am
ORD
- SJD
1 stop11h 10m
Volaris
Deal found 2/24![Volaris logo]()
$126
This Trip.com deal was found by Cheapflights users on 2/25. 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 Trip.com 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
Deal found 2/25![Volaris logo]()
$127
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 February 26, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $459 (Mytrip) |
One-way from | $94 (Kiwi.com) |
Popular in | March |
Cheapest in | September |
Average price | $626 |
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 February 26, 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
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Sat 4/11
4:10 pm-2:48 pm
1 stop24h 38m
San José del Cabo Los Cabos
Fri 4/17
2:30 pm-2:21 pm
2 stops21h 51m
$486
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Mon 4/13
8:40 am-11:25 am
Nonstop4h 45m
San José del Cabo Los Cabos
Sat 4/18
11:52 am-6:09 pm
Nonstop4h 17m
$515
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Thu 3/26
7:15 am-10:08 am
Nonstop4h 53m
San José del Cabo Los Cabos
Thu 4/2
1:17 pm-12:30 am
1 stop9h 13m
$525
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Thu 3/19
5:30 am-5:43 pm
2 stops14h 13m
San José del Cabo Los Cabos
Thu 3/26
12:35 pm-11:54 pm
1 stop9h 19m
$529
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Sat 4/11
5:10 am-10:40 am
1 stop7h 30m
San José del Cabo Los Cabos
Sat 4/18
1:55 pm-10:45 pm
1 stop6h 50m
$534
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Sat 4/11
5:59 pm-7:40 am
2 stops15h 41m
San José del Cabo Los Cabos
Sat 4/18
10:20 am-11:59 pm
2 stops11h 39m
$534
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Fri 5/15
6:24 am-5:50 pm
2 stops13h 26m
San José del Cabo Los Cabos
Wed 5/20
10:25 am-11:59 pm
2 stops11h 34m
$547
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Wed 4/15
7:00 am-1:43 pm
1 stop8h 43m
San José del Cabo Los Cabos
Mon 4/20
11:52 am-6:09 pm
Nonstop4h 17m
$547
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Thu 3/26
7:15 am-10:08 am
Nonstop4h 53m
San José del Cabo Los Cabos
Mon 3/30
11:32 am-12:45 am
1 stop11h 13m
$551
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Tue 3/31
12:47 pm-7:40 am
2 stops20h 53m
San José del Cabo Los Cabos
Sat 4/4
8:35 am-10:31 pm
2 stops11h 56m
$563
Showing 1-10 of 46 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 $322). 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 February 26, 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 February 26, 2026.
The most flights from CHI to zzKPG are scheduled on a Monday (4 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (1 on average).
Reviews of airlines servicing Los Cabos
Get insights into the airlines that provide service to Los Cabos. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Los Cabos. Reviews last updated February 26, 2026.
Peruse reviews from past customers who have flown with Southwest, United Airlines, and American 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.
Crew
8.6
Food
7.0
Boarding
8.1
Overall
8.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Food
7.0
Boarding
8.1
Overall
8.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Food
7.0
Boarding
8.1
Overall
8.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Food
7.0
Boarding
8.1
Overall
8.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Food
7.0
Boarding
8.1
Overall
8.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Food
7.0
Boarding
8.1
Overall
8.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
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.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
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 February 26, 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 February 26, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$184 | Average$500 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$252 | Average$388 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$266 | Average$358 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$416 | Average$623 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$416 | Average$606 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$485 | Average$692 | FlexibilityNo cancel fee | On-time63% |