$166+ Cheap flights from Chicago (CHI) to San José del Cabo (SJD)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJD
Nov 24 — Dec 11
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to San José del Cabo 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.Cheapflights Tip: The best prices from Chicago to San José del Cabo Los Cabos are usually found in September or June, booked 11 days in advance, depart on a Tuesday or Friday and return on a Thursday
Cheap flight deals from Chicago to San José del Cabo
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Cheapest flights from Chicago to San José del CaboExplore the most affordable flight options available from Chicago to San José del Cabo. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 25, 2026.
Explore the most affordable flight options available from Chicago to San José del Cabo. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 25, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 11/41:24 am -
1 stop10h 11m
Sat 11/78:51 pm -
1 stop25h 09m
Deal found 10/20![Multiple Airlines logo]()
$453
This Air Canada deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/168:45 am -
1 stop30h 05m
Mon 11/232:45 pm -
2 stops40h 15m
Deal found 10/21![Air Canada logo]()
$454
This FlightHub deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/910:05 am -
1 stop28h 45m
Sun 12/138:15 am -
1 stop14h 06m
Deal found 10/23![Multiple Airlines logo]()
$455
This Kiwi.com deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/91:24 am -
1 stop10h 11m
Sat 11/148:51 pm -
1 stop25h 09m
Deal found 10/21![Multiple Airlines logo]()
$456
This Kiwi.com deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 12/212:25 am -
1 stop16h 43m
Sun 12/68:15 am -
1 stop13h 45m
Deal found 10/20![Viva logo]()
$460
This Orbitz deal was found by Cheapflights users on 10/22. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/17:27 am -
1 stop8h 07m
Tue 12/811:15 am -
1 stop11h 29m
Deal found 10/22![Multiple Airlines logo]()
$462
This FlightHub deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1812:50 pm -
1 stop26h 00m
Wed 11/252:45 pm -
2 stops16h 15m
Deal found 10/21![Air Canada logo]()
$464
This Kiwi.com deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 11/281:05 am -
1 stop13h 54m
Fri 12/2512:52 pm -
1 stop9h 08m
Deal found 10/20![Viva logo]()
$465
This Priceline deal was found by Cheapflights users on 10/22. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/66:00 am -
1 stop10h 44m
Sun 12/138:15 am -
1 stop14h 06m
Deal found 10/22![Multiple Airlines logo]()
$466
This Kiwi.com deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/71:24 am -
1 stop10h 11m
Sat 11/148:51 pm -
1 stop25h 09m
Deal found 10/21![Multiple Airlines logo]()
$467
This Kiwi.com deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 11/161:24 am -
1 stop10h 11m
Tue 11/244:40 pm -
2 stops53h 15m
Deal found 10/20![Multiple Airlines logo]()
$468
This Southwest deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/155:10 am -
1 stop10h 05m
Fri 11/202:45 pm -
1 stop8h 05m
Deal found 10/21![Southwest logo]()
$523
Best flights from Chicago to San José del CaboDiscover carefully curated flight deals from Chicago to San José del Cabo that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 25, 2026.
Discover carefully curated flight deals from Chicago to San José del Cabo that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 25, 2026.
This Alaska Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 12/92:08 pm -
1 stop23h 18m
Sun 12/137:42 pm -
2 stops19h 49m
Deal found 10/21![Alaska Airlines logo]()
$494
This United Airlines deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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.
Sun 11/159:03 am -
Nonstop5h 00m
Fri 11/2012:55 pm -
Nonstop4h 16m
Deal found 10/20![United Airlines logo]()
$504
This Delta deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 12/47:45 am -
1 stop8h 08m
Tue 12/86:02 am -
2 stops13h 51m
Deal found 10/20![Delta logo]()
$572
This Southwest deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 11/146:35 am -
1 stop6h 25m
Tue 11/172:45 pm -
1 stop7h 25m
Deal found 10/20![Southwest logo]()
$585
This Volaris deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 1/156:29 am -
1 stop9h 31m
Mon 1/183:38 pm -
1 stop12h 05m
Deal found 10/20![Volaris logo]()
$592
This United Airlines deal was found by Cheapflights users on 10/22. 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.
Fri 1/85:30 am -
1 stop7h 13m
Wed 1/1312:41 pm -
Nonstop4h 16m
Deal found 10/22![United Airlines logo]()
$615
This Southwest deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 1/205:25 am -
1 stop6h 40m
Mon 1/2512:35 pm -
1 stop8h 35m
Deal found 10/20![Southwest logo]()
$625
This Alaska Airlines deal was found by Cheapflights users on 10/24. 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.
Fri 12/47:27 am -
1 stop8h 07m
Tue 12/86:40 pm -
2 stops22h 09m
Deal found 10/24![Alaska Airlines logo]()
$631
This Delta deal was found by Cheapflights users on 10/24. 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 12/76:00 am -
1 stop7h 59m
Thu 12/102:04 pm -
1 stop7h 50m
Deal found 10/24![Delta logo]()
$641
This Delta deal was found by Cheapflights users on 10/24. 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 12/15:30 am -
1 stop8h 29m
Tue 12/83:59 pm -
2 stops16h 27m
Deal found 10/24![Delta logo]()
$645
This Alaska Airlines deal was found by Cheapflights users on 10/24. 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.
Fri 12/47:27 am -
1 stop12h 05m
Mon 12/71:36 pm -
1 stop9h 23m
Deal found 10/24![Alaska Airlines logo]()
$663
This Southwest deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 1/16:05 am -
1 stop8h 05m
Wed 1/612:00 pm -
1 stop8h 00m
Deal found 10/20![Southwest logo]()
$686
This Delta deal was found by Cheapflights users on 10/24. 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 12/17:45 am -
1 stop8h 08m
Wed 12/93:59 pm -
2 stops15h 50m
Deal found 10/24![Delta logo]()
$645
This Southwest deal was found by Cheapflights users on 10/23. 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 3/1510:10 am -
Nonstop4h 45m
Sat 3/2012:20 pm -
1 stop14h 20m
Deal found 10/23![Southwest logo]()
$691
This Delta deal was found by Cheapflights users on 10/24. 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 12/76:00 am -
1 stop7h 59m
Fri 12/112:04 pm -
2 stops18h 33m
Deal found 10/24![Delta logo]()
$645
This Alaska Airlines deal was found by Cheapflights users on 10/24. 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.
Thu 12/37:58 pm -
1 stop19h 36m
Sun 12/67:42 pm -
2 stops21h 07m
Deal found 10/24![Alaska Airlines logo]()
$720
This Alaska Airlines deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 12/236:57 pm -
2 stops25h 52m
Tue 12/291:44 pm -
1 stop9h 15m
Deal found 10/20![Alaska Airlines logo]()
$724
This Alaska Airlines deal was found by Cheapflights users on 10/22. 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.
Wed 10/287:20 am -
1 stop30h 30m
Wed 11/44:22 pm -
1 stop19h 55m
Deal found 10/22![Alaska Airlines logo]()
$758
This Southwest deal was found by Cheapflights users on 10/22. 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.
Wed 2/106:10 am -
2 stops8h 45m
Mon 2/152:20 pm -
1 stop13h 10m
Deal found 10/22![Southwest logo]()
$914
This Southwest deal was found by Cheapflights users on 10/24. 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 12/289:35 pm -
2 stops15h 05m
Mon 1/44:30 pm -
1 stop10h 55m
Deal found 10/24![Southwest logo]()
$940
This Delta deal was found by Cheapflights users on 10/22. 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.
Mon 2/16:00 am -
2 stops12h 36m
Mon 2/81:30 pm -
1 stop7h 40m
Deal found 10/22![Delta logo]()
$1,017
This Southwest deal was found by Cheapflights users on 10/23. 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.
Fri 12/258:50 pm -
2 stops16h 40m
Mon 12/281:05 pm -
2 stops9h 45m
Deal found 10/23![Southwest logo]()
$1,023
This Delta deal was found by Cheapflights users on 10/24. 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.
Sat 3/276:00 am -
2 stops13h 41m
Sat 4/36:07 am -
2 stops14h 03m
Deal found 10/24![Delta logo]()
$1,049
Last-minute flights from Chicago to San José del CaboDiscover last-minute flight deals from Chicago to San José del Cabo. Data last updated October 25, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to San José del Cabo. Data last updated October 25, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 11/41:24 am -
1 stop10h 11m
Sat 11/78:51 pm -
1 stop25h 09m
Deal found 10/20![Multiple Airlines logo]()
$453
This Kiwi.com deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/71:24 am -
1 stop10h 11m
Sat 11/148:51 pm -
1 stop25h 09m
Deal found 10/21![Multiple Airlines logo]()
$467
This Kiwi.com deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/76:29 am -
1 stop9h 31m
Thu 11/124:12 pm -
2 stops31h 09m
Deal found 10/21![Multiple Airlines logo]()
$470
This Kiwi.com deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/91:24 am -
1 stop10h 11m
Sat 11/148:51 pm -
1 stop25h 09m
Deal found 10/21![Multiple Airlines logo]()
$456
This Justfly.com deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/91:24 am -
1 stop10h 11m
Sat 11/143:38 pm -
1 stop12h 05m
Deal found 10/21![Volaris logo]()
$462
This Mytrip deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/141:24 am -
1 stop10h 11m
Sun 11/221:28 pm -
1 stop9h 21m
Deal found 10/21![Multiple Airlines logo]()
$469
This Orbitz deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/147:20 am -
1 stop11h 28m
Tue 11/1711:15 am -
1 stop11h 29m
Deal found 10/21![Multiple Airlines logo]()
$471
This Air Canada deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/168:45 am -
1 stop30h 05m
Mon 11/232:45 pm -
2 stops40h 15m
Deal found 10/21![Air Canada logo]()
$454
This Kiwi.com deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 11/161:24 am -
1 stop10h 11m
Tue 11/244:40 pm -
2 stops53h 15m
Deal found 10/20![Multiple Airlines logo]()
$468
This FlightHub deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1812:50 pm -
1 stop26h 00m
Wed 11/252:45 pm -
2 stops16h 15m
Deal found 10/21![Air Canada logo]()
$464
This Kiwi.com deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” 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 11/281:05 am -
1 stop13h 54m
Wed 12/93:21 pm -
1 stop7h 23m
Deal found 10/19![Multiple Airlines logo]()
$460
This Kiwi.com deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 11/281:05 am -
1 stop13h 54m
Fri 12/2512:52 pm -
1 stop9h 08m
Deal found 10/20![Viva logo]()
$465
One-way flights from Chicago to San José del CaboSearch for one-way flight options from Chicago to San José del Cabo. Find affordable one-way fares based on user searches. Data last updated October 25, 2026.
Search for one-way flight options from Chicago to San José del Cabo. Find affordable one-way fares based on user searches. Data last updated October 25, 2026.
This Alaska Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/147:20 am -
1 stop11h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Alaska Airlines logo]()
$166
This Super.com deal was found by Cheapflights users on 10/22. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/106:29 am -
1 stop9h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Volaris logo]()
$172
This Super.com deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” 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 11/116:29 am -
1 stop9h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Volaris logo]()
$174
This Viva deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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.
Sat 10/3112:30 pm -
1 stop29h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Viva logo]()
$179
This American Airlines deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 11/176:00 am -
1 stop9h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![American Airlines logo]()
$181
This Viva deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” 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.
Tue 12/2912:49 pm -
1 stop28h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Viva logo]()
$189
This Super.com deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/81:24 am -
1 stop10h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Volaris logo]()
$192
This Kiwi.com deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/161:24 am -
1 stop10h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Volaris logo]()
$197
This Air Canada deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/254:30 pm -
1 stop22h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Air Canada logo]()
$203
This Kiwi.com deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” 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 11/1512:35 am -
2 stops13h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Multiple Airlines logo]()
$204
This Kiwi.com deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 11/3012:25 am -
1 stop16h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Viva logo]()
$205
This Kiwi.com deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/96:42 pm -
3 stops22h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Multiple Airlines logo]()
$236
Find flight deals from Chicago to San José del Cabo
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to San José del Cabo (SJD). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated October 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $452 (Kiwi.com) |
One-way from | $166 (Alaska Airlines) |
Popular in | December |
Cheapest in | September |
Average price | $681 |
Good round-trip deal | $687 or less |
Good one-way deal | $289 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to San José del Cabo 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 7,457,451 searches. Data last updated October 25, 2026.
Use the filters below to find and compare flights from Chicago to San José del Cabo that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSan José del Cabo
ORD Chicago O'Hare Intl - SJD San José del Cabo Los Cabos
ORDSJD
Chicago O'Hare Intl
Sat 11/14
7:20 am-5:48 pm
1 stop11h 28m
San José del Cabo Los Cabos
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$166
ChicagoSan José del Cabo
ORD Chicago O'Hare Intl - SJD San José del Cabo Los Cabos
ORDSJD
Chicago O'Hare Intl
Tue 12/29
12:49 pm-4:08 pm
1 stop28h 19m
San José del Cabo Los Cabos
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$189
ChicagoSan José del Cabo
ORD Chicago O'Hare Intl - SJD San José del Cabo Los Cabos
ORDSJD
Chicago O'Hare Intl
Wed 11/25
4:30 pm-1:50 pm
1 stop22h 20m
San José del Cabo Los Cabos
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$203
ChicagoSan José del Cabo
ORD Chicago O'Hare Intl - SJD San José del Cabo Los Cabos
ORDSJD
Chicago O'Hare Intl
Wed 11/4
12:35 am-4:10 pm
1 stop16h 35m
San José del Cabo Los Cabos
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$212
ChicagoSan José del Cabo
ORD Chicago O'Hare Intl - SJD San José del Cabo Los Cabos
ORDSJD
Chicago O'Hare Intl
Sun 11/15
7:20 am-4:00 pm
1 stop9h 40m
San José del Cabo Los Cabos
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$218
Quickest round-trip
ChicagoSan José del Cabo
ORD Chicago O'Hare Intl - SJD San José del Cabo Los Cabos
ORDSJD
Chicago O'Hare Intl
Mon 11/16
9:03 am-1:03 pm
Nonstop5h 00m
San José del Cabo Los Cabos
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$233
ChicagoSan José del Cabo
MDW Chicago Midway - SJD San José del Cabo Los Cabos
MDWSJD
Chicago Midway
Tue 11/17
5:20 am-11:40 am
1 stop7h 20m
San José del Cabo Los Cabos
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$240
ChicagoSan José del Cabo
MDW Chicago Midway - SJD San José del Cabo Los Cabos
MDWSJD
Chicago Midway
Tue 12/1
12:33 pm-8:51 pm
3 stops57h 18m
San José del Cabo Los Cabos
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$253
ChicagoSan José del Cabo
ORD Chicago O'Hare Intl - SJD San José del Cabo Los Cabos
ORDSJD
Chicago O'Hare Intl
Wed 12/30
7:58 pm-12:10 pm
1 stop17h 12m
San José del Cabo Los Cabos
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$259
ChicagoSan José del Cabo
MDW Chicago Midway - SJD San José del Cabo Los Cabos
MDWSJD
Chicago Midway
Sun 11/8
6:20 pm-4:31 pm
2 stops23h 11m
San José del Cabo Los Cabos
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$282
Showing 1-10 of 39 resultsSorted by cheapest first
Compare providers for flights from Chicago to San José del Cabo
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to San José del Cabo in October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago-San José del Cabo flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-San José del Cabo flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-San José del Cabo flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-San José del Cabo flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-San José del Cabo flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Chicago to San José del Cabo
Have a flexible travel schedule? Discover the best time to fly to San José del Cabo from Chicago with our price prediction graph.
CHI-SJD
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 San José del Cabo
CHI-SJD
ORD-SJD
MDW-SJD
What is the cheapest month to book a flight from Chicago to San José del Cabo?
Currently, September is the cheapest month in which you can book a flight from Chicago to San José del Cabo (average of $489). Flying from Chicago to San José del Cabo in December is currently the most expensive (average of $731). 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 SJD?
Find hourly flight availability from Chicago to San José del Cabo. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 25, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to San José del Cabo as you normally would.
Weekly flight availability from Chicago to San José del Cabo
Explore weekly flight availability from Chicago to San José del Cabo. 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 October 25, 2026.
The most flights from CHI to SJD are scheduled on a Friday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).
How much does it cost to fly round-trip from Chicago to San José del Cabo?
Airfare is below average for this route at the moment.
Chicago to San José del Cabo flights typically cost between $583 and $832 in January.The cheapest round-trip price found within the last 5 days was $452 on Viva (Jan 14-Jan 19).
How far ahead should I book a flight from Chicago to San José del Cabo?
Booking 16 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to San José del Cabo. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
Reviews of airlines servicing San José del Cabo
Get insights into the airlines that provide service to San José del Cabo. 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 San José del Cabo. Reviews last updated October 25, 2026.
Peruse reviews from past customers who have flown with Southwest,United Airlines, andAmerican Airlines from Chicago to San José del Cabo to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Entertainment
7.4
Comfort
8.0
Overall
7.9
Boarding
8.1
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Crew
8.6
Entertainment
7.4
Comfort
8.0
Overall
7.9
Boarding
8.1
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Crew
8.6
Entertainment
7.4
Comfort
8.0
Overall
7.9
Boarding
8.1
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Crew
8.6
Entertainment
7.4
Comfort
8.0
Overall
7.9
Boarding
8.1
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Crew
8.6
Entertainment
7.4
Comfort
8.0
Overall
7.9
Boarding
8.1
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Crew
8.6
Entertainment
7.4
Comfort
8.0
Overall
7.9
Boarding
8.1
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Related info for your journey
Find useful and relevant information for your journey from Chicago to San José del Cabo. 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 San José del Cabo
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Complete your trip
Complete your trip to San José del Cabo by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to San José del Cabo by cabin class
Find flights from Chicago to San José del Cabo, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and San José del Cabo flights
Browse other Chicago and San José del Cabo flight options. Last updated on October 25, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on October 25, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Other flights to San José del Cabo
Explore flights to San José del Cabo departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on October 25, 2026.
Top 5 airlines flying from Chicago to San José del Cabo
Discover the top 5 airlines that operate flights from Chicago to San José del Cabo. 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 7,457,451 searches. Data last updated October 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$207 | Average$412 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$223 | Average$434 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$434 | Average$671 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$475 | Average$700 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$483 | Average$687 | FlexibilityNo cancel fee | On-time71% |