$118+ 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 2/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJD
Oct 30 — Nov 61
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 June or September, booked 81 days in advance, depart on a Tuesday or Friday and return on a Monday
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 September 30, 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 September 30, 2026.
This Trip.com deal was found by Cheapflights users on 9/26. 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.
Tue 12/11:05 am -
1 stop13h 48m
Mon 12/78:15 am -
1 stop13h 45m
Deal found 9/26![Viva logo]()
$379
This Kiwi.com deal was found by Cheapflights users on 9/25. 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.
Tue 11/246:29 am -
1 stop9h 31m
Thu 11/268:49 am -
2 stops13h 06m
Deal found 9/25![Multiple Airlines logo]()
$382
This Kiwi.com deal was found by Cheapflights users on 9/25. 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.
Mon 11/96:29 am -
1 stop9h 31m
Thu 11/128:49 am -
2 stops13h 06m
Deal found 9/25![Multiple Airlines logo]()
$386
This Super.com deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 10/191:40 am -
1 stop10h 29m
Tue 10/273:53 pm -
1 stop11h 50m
Deal found 9/29![Volaris logo]()
$387
This Kiwi.com deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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 10/72:41 am -
2 stops37h 34m
Mon 10/123:15 pm -
1 stop7h 26m
Deal found 9/28![Multiple Airlines logo]()
$388
This Kiwi.com deal was found by Cheapflights users on 9/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/246:29 am -
1 stop9h 31m
Wed 11/253:15 pm -
1 stop8h 26m
Deal found 9/27![Volaris logo]()
$389
This Kiwi.com deal was found by Cheapflights users on 9/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/182:41 am -
2 stops19h 09m
Fri 11/277:27 am -
1 stop14h 23m
Deal found 9/27![Multiple Airlines logo]()
$390
This Super.com deal was found by Cheapflights users on 9/25. 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.
Sun 10/112:53 am -
1 stop10h 36m
Thu 10/1512:02 pm -
1 stop9h 45m
Deal found 9/25![Volaris logo]()
$397
This Kiwi.com deal was found by Cheapflights users on 9/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/246:29 am -
1 stop9h 31m
Fri 11/277:27 am -
1 stop14h 23m
Deal found 9/27![Multiple Airlines logo]()
$398
This Kiwi.com deal was found by Cheapflights users on 9/26. 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.
Fri 12/46:17 pm -
1 stop22h 51m
Tue 12/89:31 pm -
1 stop18h 16m
Deal found 9/26![Multiple Airlines logo]()
$530
This Kiwi.com deal was found by Cheapflights users on 9/26. 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.
Fri 11/66:17 pm -
1 stop21h 29m
Tue 11/109:31 pm -
1 stop18h 16m
Deal found 9/26![Multiple Airlines logo]()
$546
This Kiwi.com deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 11/16:17 pm -
1 stop13h 30m
Thu 11/59:31 pm -
1 stop18h 16m
Deal found 9/29![Multiple Airlines logo]()
$556
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 September 30, 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 September 30, 2026.
This Volaris deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/181:40 am -
1 stop10h 29m
Thu 10/227:47 pm -
1 stop8h 05m
Deal found 9/29![Volaris logo]()
$482
This Alaska Airlines deal was found by Cheapflights users on 9/26. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/17:57 pm -
2 stops18h 47m
Thu 11/55:10 pm -
2 stops24h 49m
Deal found 9/26![Alaska Airlines logo]()
$581
This Southwest deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 1/116:10 am -
2 stops8h 45m
Tue 1/1212:00 pm -
2 stops10h 00m
Deal found 9/29![Southwest logo]()
$583
This Delta deal was found by Cheapflights users on 9/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/126:00 am -
1 stop7h 59m
Tue 12/152:04 pm -
1 stop7h 50m
Deal found 9/27![Delta logo]()
$701
This Volaris deal was found by Cheapflights users on 9/25. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/71:40 am -
1 stop10h 29m
Mon 10/127:47 pm -
1 stop8h 05m
Deal found 9/25![Volaris logo]()
$524
This Alaska Airlines deal was found by Cheapflights users on 9/25. 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.
Mon 10/192:21 pm -
2 stops23h 14m
Thu 10/2210:43 am -
1 stop11h 16m
Deal found 9/25![Alaska Airlines logo]()
$584
This Volaris deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/196:29 am -
1 stop9h 31m
Tue 11/2411:15 am -
1 stop11h 29m
Deal found 9/28![Volaris logo]()
$541
This Alaska Airlines deal was found by Cheapflights users on 9/25. 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.
Sat 11/142:07 pm -
2 stops21h 38m
Tue 11/174:22 pm -
1 stop25h 37m
Deal found 9/25![Alaska Airlines logo]()
$589
This Southwest deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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 3/15:15 am -
2 stops8h 40m
Sat 3/611:00 am -
2 stops10h 45m
Deal found 9/28![Southwest logo]()
$649
This Alaska Airlines deal was found by Cheapflights users on 9/25. 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.
Sat 12/127:27 am -
1 stop12h 05m
Tue 12/156:40 pm -
2 stops22h 09m
Deal found 9/25![Alaska Airlines logo]()
$602
This Southwest deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 1/45:55 am -
1 stop8h 55m
Sun 2/2810:55 am -
1 stop11h 25m
Deal found 9/29![Southwest logo]()
$666
This Delta deal was found by Cheapflights users on 9/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/246:00 am -
1 stop7h 59m
Thu 11/266:02 am -
2 stops15h 52m
Deal found 9/27![Delta logo]()
$737
This Alaska Airlines deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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 10/297:49 pm -
1 stop22h 49m
Thu 11/511:55 am -
1 stop10h 54m
Deal found 9/28![Alaska Airlines logo]()
$619
This Delta deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 -
1 stop7h 25m
Mon 2/81:30 pm -
1 stop7h 40m
Deal found 9/29![Delta logo]()
$780
This Alaska Airlines deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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.
Mon 12/287:58 pm -
1 stop17h 46m
Thu 1/71:10 pm -
1 stop7h 58m
Deal found 9/29![Alaska Airlines logo]()
$626
This Southwest deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 10/165:15 am -
2 stops10h 25m
Tue 10/2011:05 am -
2 stops9h 15m
Deal found 9/29![Southwest logo]()
$763
This Delta deal was found by Cheapflights users on 9/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/316:00 am -
1 stop7h 52m
Sun 1/101:30 pm -
1 stop7h 40m
Deal found 9/27![Delta logo]()
$846
This Alaska Airlines deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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 12/96:00 am -
2 stops12h 30m
Sun 12/137:42 pm -
2 stops21h 07m
Deal found 9/28![Alaska Airlines logo]()
$667
This Delta deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 11/236:00 am -
2 stops17h 35m
Tue 12/12:04 pm -
1 stop7h 50m
Deal found 9/29![Delta logo]()
$882
This Delta deal was found by Cheapflights users on 9/26. 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.
Tue 10/206:04 am -
1 stop7h 16m
Fri 10/2312:25 pm -
1 stop8h 08m
Deal found 9/26![Delta logo]()
$917
This Delta deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 1/26:00 am -
2 stops14h 18m
Thu 1/71:30 pm -
1 stop7h 40m
Deal found 9/29![Delta logo]()
$977
This Delta deal was found by Cheapflights users on 9/26. 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 11/16:04 am -
1 stop7h 16m
Thu 11/51:25 pm -
1 stop8h 08m
Deal found 9/26![Delta logo]()
$981
Last-minute flights from Chicago to San José del CaboDiscover last-minute flight deals from Chicago to San José del Cabo. Data last updated September 30, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to San José del Cabo. Data last updated September 30, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 9/25. 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.
Tue 10/61:49 pm -
2 stops31h 35m
Fri 10/912:06 pm -
1 stop10h 49m
Deal found 9/25![Multiple Airlines logo]()
$454
This Cheapflightsfares deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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.
Tue 10/62:53 am -
1 stop10h 36m
Wed 10/2112:02 pm -
1 stop9h 45m
Deal found 9/28![Volaris logo]()
$459
This Kiwi.com deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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 10/72:41 am -
2 stops37h 34m
Mon 10/123:15 pm -
1 stop7h 26m
Deal found 9/28![Multiple Airlines logo]()
$388
This Super.com deal was found by Cheapflights users on 9/27. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/71:40 am -
1 stop10h 29m
Mon 10/127:47 pm -
1 stop8h 05m
Deal found 9/27![Volaris logo]()
$418
This Super.com deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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 10/71:40 am -
1 stop10h 29m
Thu 10/157:47 pm -
1 stop8h 05m
Deal found 9/28![Volaris logo]()
$423
This Kiwi.com deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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 10/71:49 pm -
2 stops22h 20m
Mon 10/123:15 pm -
1 stop7h 26m
Deal found 9/28![Volaris logo]()
$425
This Viva deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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 10/93:00 pm -
1 stop22h 43m
Tue 10/131:20 pm -
1 stop8h 39m
Deal found 9/28![Viva logo]()
$417
This Super.com deal was found by Cheapflights users on 9/26. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/97:35 am -
1 stop13h 29m
Mon 10/127:47 pm -
1 stop8h 05m
Deal found 9/26![Volaris logo]()
$443
This Super.com deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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 10/97:35 am -
1 stop13h 29m
Tue 10/137:47 pm -
1 stop8h 05m
Deal found 9/28![Volaris logo]()
$456
This Justfly.com deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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.
Fri 10/97:35 am -
1 stop13h 29m
Sat 10/1712:02 pm -
1 stop9h 45m
Deal found 9/28![Volaris logo]()
$462
This Kiwi.com deal was found by Cheapflights users on 9/25. 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.
Mon 10/128:23 pm -
1 stop17h 06m
Thu 10/1512:06 pm -
1 stop28h 58m
Deal found 9/25![Volaris logo]()
$575
This Delta deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 10/206:04 am -
1 stop7h 16m
Fri 10/236:15 am -
2 stops14h 18m
Deal found 9/29![Delta logo]()
$579
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 September 30, 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 September 30, 2026.
This Viva deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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.
Wed 11/412:25 am -
1 stop16h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Viva logo]()
$118
This Kiwi.com deal was found by Cheapflights users on 9/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/131:24 am -
1 stop15h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![Multiple Airlines logo]()
$141
This Viva deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 3/91:10 am -
1 stop13h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Viva logo]()
$151
This Viva deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 12/51:05 am -
1 stop13h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Viva logo]()
$154
This Super.com deal was found by Cheapflights users on 9/25. 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 10/122:53 am -
1 stop10h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Volaris logo]()
$158
This Super.com deal was found by Cheapflights users on 9/27. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/62:53 am -
1 stop10h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![Volaris logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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 10/52:41 am -
3 stops31h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Multiple Airlines logo]()
$161
This FlightHub deal was found by Cheapflights users on 9/25. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/121:24 am -
1 stop10h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Volaris logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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 10/51:40 am -
1 stop10h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Volaris logo]()
$168
This Super.com deal was found by Cheapflights users on 9/27. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/66:29 am -
1 stop9h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![Volaris logo]()
$169
This Kiwi.com deal was found by Cheapflights users on 9/25. 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 11/262:28 pm -
2 stops50h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Multiple Airlines logo]()
$204
This Kiwi.com deal was found by Cheapflights users on 9/25. 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.
Fri 11/278:07 am -
2 stops33h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Multiple Airlines logo]()
$206
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 September 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $378 (FlightHub) |
One-way from | $118 (Viva) |
Popular in | December |
Cheapest in | June |
Average price | $497 |
Good round-trip deal | $653 or less |
Good one-way deal | $256 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 September 30, 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
Fri 2/12
12:25 am-1:07 pm
1 stop13h 42m
San José del Cabo Los Cabos
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$118
ChicagoSan José del Cabo
ORD Chicago O'Hare Intl - SJD San José del Cabo Los Cabos
ORDSJD
Chicago O'Hare Intl
Fri 12/25
12:25 am-4:08 pm
1 stop16h 43m
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 11/30
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
$263
ChicagoSan José del Cabo
ORD Chicago O'Hare Intl - SJD San José del Cabo Los Cabos
ORDSJD
Chicago O'Hare Intl
Sun 3/28
2:19 am-10:35 am
1 stop10h 16m
San José del Cabo Los Cabos
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$265
ChicagoSan José del Cabo
MDW Chicago Midway - SJD San José del Cabo Los Cabos
MDWSJD
Chicago Midway
Mon 10/26
5:31 pm-1:25 pm
2 stops21h 54m
San José del Cabo Los Cabos
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$268
ChicagoSan José del Cabo
MDW Chicago Midway - SJD San José del Cabo Los Cabos
MDWSJD
Chicago Midway
Wed 10/28
6:25 am-12:35 pm
1 stop8h 10m
San José del Cabo Los Cabos
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$268
ChicagoSan José del Cabo
MDW Chicago Midway - SJD San José del Cabo Los Cabos
MDWSJD
Chicago Midway
Mon 10/26
7:10 am-12:10 pm
1 stop7h 00m
San José del Cabo Los Cabos
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$268
ChicagoSan José del Cabo
MDW Chicago Midway - SJD San José del Cabo Los Cabos
MDWSJD
Chicago Midway
Mon 11/30
9:35 pm-12:50 pm
2 stops16h 15m
San José del Cabo Los Cabos
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$274
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-6:26 pm
1 stop23h 28m
San José del Cabo Los Cabos
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$287
ChicagoSan José del Cabo
MDW Chicago Midway - SJD San José del Cabo Los Cabos
MDWSJD
Chicago Midway
Tue 3/23
6:00 am-11:30 am
1 stop7h 30m
San José del Cabo Los Cabos
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$289
Showing 1-10 of 40 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 September.
| 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 $492). Flying from Chicago to San José del Cabo in December is currently the most expensive (average of $721). 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 September 30, 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 September 30, 2026.
The most flights from CHI to SJD are scheduled on a Monday (2 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 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 $487 and $731 in January.The cheapest round-trip price found within the last 5 days was $378 on Volaris (Jan 31-Feb 8).
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 September 30, 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.
Food
7.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Overall
8.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Overall
8.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Overall
8.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Overall
8.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Overall
8.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Overall
8.0
Comfort
8.0
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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San José del Cabo flight routes
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 September 30, 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 September 30, 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 September 30, 2026.
Top 4 airlines flying from Chicago to San José del Cabo
Discover the top 4 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 September 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$207 | Average$403 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$435 | Average$669 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$464 | Average$678 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$475 | Average$718 | FlexibilityNo cancel fee | On-time63% |