$130+ Cheap flights from Chicago (CHI) to San José del Cabo (SJD)
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 11/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJD
Sep 29 — Oct 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 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 August 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 August 30, 2026.
This Super.com deal was found by Cheapflights users on 8/26. 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.
Mon 10/197:35 am -
1 stop13h 29m
Fri 10/237:47 pm -
1 stop8h 05m
Deal found 8/26![Volaris logo]()
$349
This Super.com deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/67:35 am -
1 stop13h 29m
Sat 10/107:47 pm -
1 stop8h 05m
Deal found 8/25![Volaris logo]()
$350
This Super.com deal was found by Cheapflights users on 8/27. 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
Fri 12/113:21 pm -
1 stop7h 23m
Deal found 8/27![Volaris logo]()
$354
This Super.com deal was found by Cheapflights users on 8/28. 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.
Sat 10/37:35 am -
1 stop13h 29m
Sat 10/107:47 pm -
1 stop8h 05m
Deal found 8/28![Volaris logo]()
$356
This Super.com deal was found by Cheapflights users on 8/27. 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 10/77:35 am -
1 stop13h 29m
Wed 10/217:47 pm -
1 stop8h 05m
Deal found 8/27![Volaris logo]()
$357
This Super.com deal was found by Cheapflights users on 8/27. 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.
Fri 10/27:35 am -
1 stop13h 29m
Tue 10/67:47 pm -
1 stop8h 05m
Deal found 8/27![Volaris logo]()
$358
This FlightHub deal was found by Cheapflights users on 8/27. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/287:35 am -
1 stop13h 29m
Sat 10/37:47 pm -
1 stop8h 05m
Deal found 8/27![Volaris logo]()
$359
This Super.com deal was found by Cheapflights users on 8/28. 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 11/66:29 am -
1 stop9h 31m
Tue 11/103:21 pm -
1 stop7h 23m
Deal found 8/28![Volaris logo]()
$360
This Super.com deal was found by Cheapflights users on 8/25. 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.
Sat 12/56:29 am -
1 stop9h 31m
Wed 12/93:21 pm -
1 stop7h 23m
Deal found 8/25![Volaris logo]()
$361
This Kiwi.com deal was found by Cheapflights users on 8/29. 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.
Fri 10/238:23 pm -
1 stop20h 28m
Fri 12/47:26 am -
1 stop8h 21m
Deal found 8/29![Multiple Airlines logo]()
$524
This Delta deal was found by Cheapflights users on 8/25. 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.
Mon 10/196:04 am -
1 stop7h 16m
Fri 10/236:15 am -
2 stops14h 18m
Deal found 8/25![Delta logo]()
$541
This Southwest deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/85:55 am -
2 stops9h 20m
Wed 11/1111:50 am -
2 stops9h 45m
Deal found 8/26![Southwest logo]()
$546
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 August 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 August 30, 2026.
This Volaris deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/272:53 am -
1 stop10h 36m
Wed 11/43:21 pm -
1 stop7h 23m
Deal found 8/26![Volaris logo]()
$513
This Southwest deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/85:55 am -
2 stops9h 20m
Wed 11/112:45 pm -
1 stop7h 20m
Deal found 8/26![Southwest logo]()
$546
This United Airlines deal was found by Cheapflights users on 8/25. 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 10/195:00 am -
1 stop9h 05m
Fri 10/2311:52 am -
Nonstop4h 15m
Deal found 8/25![United Airlines logo]()
$553
This Alaska Airlines deal was found by Cheapflights users on 8/28. 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.
Sat 11/142:15 pm -
2 stops24h 29m
Sat 11/217:58 pm -
2 stops22h 01m
Deal found 8/28![Alaska Airlines logo]()
$596
This Delta deal was found by Cheapflights users on 8/27. 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 10/245:27 am -
1 stop7h 53m
Sat 10/316:02 am -
2 stops15h 55m
Deal found 8/27![Delta logo]()
$645
This Southwest deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/147:35 am -
1 stop7h 45m
Tue 11/172:05 pm -
1 stop9h 05m
Deal found 8/27![Southwest logo]()
$571
This Volaris deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/216:29 am -
1 stop9h 31m
Thu 11/2611:15 am -
1 stop11h 29m
Deal found 8/27![Volaris logo]()
$589
This Alaska Airlines deal was found by Cheapflights users on 8/25. 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.
Thu 10/295:46 pm -
2 stops20h 04m
Thu 11/55:10 pm -
2 stops24h 49m
Deal found 8/25![Alaska Airlines logo]()
$632
This Southwest deal was found by Cheapflights users on 8/25. 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.
Tue 10/276:05 am -
1 stop8h 00m
Sun 11/14:30 pm -
1 stop10h 55m
Deal found 8/25![Southwest logo]()
$582
This Delta deal was found by Cheapflights users on 8/29. 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.
Wed 10/287:29 am -
1 stop7h 56m
Wed 11/41:25 pm -
2 stops17h 16m
Deal found 8/29![Delta logo]()
$648
This United Airlines deal was found by Cheapflights users on 8/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/278:52 am -
Nonstop4h 33m
Sat 10/311:52 am -
Nonstop4h 15m
Deal found 8/27![United Airlines logo]()
$677
This Volaris deal was found by Cheapflights users on 8/29. 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.
Fri 11/206:29 am -
1 stop9h 31m
Fri 11/2711:15 am -
1 stop11h 29m
Deal found 8/29![Volaris logo]()
$645
This Alaska Airlines deal was found by Cheapflights users on 8/25. 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 10/97:20 am -
1 stop11h 18m
Fri 10/165:48 pm -
2 stops23h 05m
Deal found 8/25![Alaska Airlines logo]()
$672
This Southwest deal was found by Cheapflights users on 8/28. 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 10/56:45 am -
1 stop7h 20m
Wed 10/211:30 pm -
1 stop7h 45m
Deal found 8/28![Southwest logo]()
$643
This Alaska Airlines deal was found by Cheapflights users on 8/25. 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.
Sun 10/187:20 am -
1 stop11h 18m
Mon 11/25:10 pm -
2 stops29h 49m
Deal found 8/25![Alaska Airlines logo]()
$690
This Southwest deal was found by Cheapflights users on 8/29. 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.
Sat 10/36:35 am -
2 stops8h 15m
Tue 10/611:05 am -
2 stops9h 15m
Deal found 8/29![Southwest logo]()
$673
This Alaska Airlines deal was found by Cheapflights users on 8/27. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/302:14 pm -
2 stops21h 19m
Fri 11/64:06 pm -
2 stops12h 34m
Deal found 8/27![Alaska Airlines logo]()
$690
This Southwest deal was found by Cheapflights users on 8/29. 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.
Wed 10/146:05 am -
2 stops9h 35m
Mon 1/1112:00 pm -
2 stops10h 00m
Deal found 8/29![Southwest logo]()
$698
This Southwest deal was found by Cheapflights users on 8/28. 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.
Fri 11/275:20 am -
2 stops9h 55m
Tue 12/111:50 am -
2 stops8h 40m
Deal found 8/28![Southwest logo]()
$725
This Southwest deal was found by Cheapflights users on 8/28. 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.
Sun 9/67:50 am -
1 stop7h 20m
Sat 9/121:10 pm -
1 stop6h 50m
Deal found 8/28![Southwest logo]()
$830
This Southwest deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/255:30 am -
2 stops9h 20m
Sun 9/272:05 pm -
1 stop8h 25m
Deal found 8/25![Southwest logo]()
$870
This Southwest deal was found by Cheapflights users on 8/29. 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.
Thu 11/59:25 pm -
2 stops15h 15m
Sun 11/83:45 pm -
1 stop13h 00m
Deal found 8/29![Southwest logo]()
$905
Last-minute flights from Chicago to San José del CaboDiscover last-minute flight deals from Chicago to San José del Cabo. Data last updated August 30, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to San José del Cabo. Data last updated August 30, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/37:35 am -
1 stop13h 29m
Tue 9/2912:06 pm -
1 stop10h 49m
Deal found 8/25![Volaris logo]()
$456
This Super.com deal was found by Cheapflights users on 8/27. 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.
Thu 9/37:35 am -
1 stop13h 29m
Thu 9/103:36 pm -
1 stop7h 19m
Deal found 8/27![Volaris logo]()
$472
This Super.com deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/47:35 am -
1 stop13h 29m
Tue 9/87:47 pm -
1 stop8h 05m
Deal found 8/25![Volaris logo]()
$434
This Super.com deal was found by Cheapflights users on 8/26. 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.
Sat 9/57:35 am -
1 stop13h 29m
Wed 9/97:47 pm -
1 stop8h 05m
Deal found 8/26![Volaris logo]()
$426
This Super.com deal was found by Cheapflights users on 8/26. 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.
Sat 9/57:35 am -
1 stop13h 29m
Thu 9/103:36 pm -
1 stop7h 19m
Deal found 8/26![Volaris logo]()
$437
This Super.com deal was found by Cheapflights users on 8/28. 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.
Sun 9/67:35 am -
1 stop13h 29m
Sat 9/123:36 pm -
1 stop7h 19m
Deal found 8/28![Volaris logo]()
$419
This Super.com deal was found by Cheapflights users on 8/25. 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 9/71:40 am -
1 stop10h 29m
Fri 9/1112:02 pm -
1 stop9h 45m
Deal found 8/25![Volaris logo]()
$378
This FlightHub deal was found by Cheapflights users on 8/29. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/77:35 am -
1 stop13h 29m
Thu 9/103:36 pm -
1 stop7h 19m
Deal found 8/29![Volaris logo]()
$384
This Super.com deal was found by Cheapflights users on 8/29. 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 9/77:35 am -
1 stop13h 29m
Fri 9/1112:02 pm -
1 stop9h 45m
Deal found 8/29![Volaris logo]()
$467
This Southwest deal was found by Cheapflights users on 8/25. 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 9/196:50 am -
1 stop6h 15m
Wed 9/2311:40 am -
1 stop9h 35m
Deal found 8/25![Southwest logo]()
$582
This Kiwi.com deal was found by Cheapflights users on 8/25. 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 9/258:23 pm -
1 stop18h 03m
Fri 10/28:05 am -
2 stops32h 00m
Deal found 8/25![Multiple Airlines logo]()
$586
This Delta deal was found by Cheapflights users on 8/27. 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.
Mon 9/286:05 am -
1 stop7h 02m
Sat 10/36:15 am -
2 stops14h 29m
Deal found 8/27![Delta logo]()
$571
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 August 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 August 30, 2026.
This Booking.com deal was found by Cheapflights users on 8/27. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1112:35 am -
1 stop21h 15m
Deal found 8/27![Viva logo]()
$130
This Kiwi.com deal was found by Cheapflights users on 8/26. 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.
Tue 9/227:35 am -
1 stop13h 29m
Deal found 8/26![Volaris logo]()
$141
This Kiwi.com deal was found by Cheapflights users on 8/25. 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 9/217:35 am -
1 stop13h 29m
Deal found 8/25![Volaris logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 8/28. 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 9/281:40 am -
1 stop10h 29m
Deal found 8/28![Volaris logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 8/26. 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.
Mon 9/287:35 am -
1 stop13h 29m
Deal found 8/26![Volaris logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 8/29. 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.
Tue 9/87:35 am -
1 stop13h 29m
Deal found 8/29![Volaris logo]()
$155
This Jetabroad deal was found by Cheapflights users on 8/29. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/17:35 am -
1 stop13h 29m
Deal found 8/29![Volaris logo]()
$156
This Kiwi.com deal was found by Cheapflights users on 8/29. 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.
Fri 10/27:35 am -
1 stop13h 29m
Deal found 8/29![Volaris logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 8/29. 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.
Mon 9/288:23 pm -
1 stop18h 03m
Deal found 8/29![Multiple Airlines logo]()
$218
This Kiwi.com deal was found by Cheapflights users on 8/26. 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.
Sat 10/103:30 pm -
2 stops28h 30m
Deal found 8/26![Multiple Airlines logo]()
$228
This Kiwi.com deal was found by Cheapflights users on 8/25. 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 9/218:23 pm -
1 stop17h 06m
Deal found 8/25![Volaris logo]()
$235
This Kiwi.com deal was found by Cheapflights users on 8/27. 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.
Sat 9/261:06 pm -
2 stops30h 54m
Deal found 8/27![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 August 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $349 (Kiwi.com) |
One-way from | $130 (Booking.com) |
Popular in | March |
Cheapest in | September |
Average price | $593 |
Good round-trip deal | $615 or less |
Good one-way deal | $320 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 August 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
Tue 10/27
2:53 am-11:29 am
1 stop10h 36m
San José del Cabo Los Cabos
Wed 11/4
3:21 pm-11:44 pm
1 stop7h 23m
$513
ChicagoSan José del Cabo
MDW Chicago Midway - SJD San José del Cabo Los Cabos
MDWSJD
Chicago Midway
Sun 11/8
5:55 am-2:15 pm
2 stops9h 20m
San José del Cabo Los Cabos
Wed 11/11
2:45 pm-11:05 pm
1 stop7h 20m
$546
ChicagoSan José del Cabo
ORD Chicago O'Hare Intl - SJD San José del Cabo Los Cabos
ORDSJD
Chicago O'Hare Intl
Mon 10/19
5:00 am-12:05 pm
1 stop9h 05m
San José del Cabo Los Cabos
Fri 10/23
11:52 am-6:07 pm
Nonstop4h 15m
$553
ChicagoSan José del Cabo
MDW Chicago Midway - SJD San José del Cabo Los Cabos
MDWSJD
Chicago Midway
Sat 11/14
7:35 am-2:20 pm
1 stop7h 45m
San José del Cabo Los Cabos
Tue 11/17
2:05 pm-12:10 am
1 stop9h 05m
$571
ChicagoSan José del Cabo
MDW Chicago Midway - SJD San José del Cabo Los Cabos
MDWSJD
Chicago Midway
Tue 10/27
6:05 am-12:05 pm
1 stop8h 00m
San José del Cabo Los Cabos
Sun 11/1
4:30 pm-4:25 am
1 stop10h 55m
$582
ChicagoSan José del Cabo
ORD Chicago O'Hare Intl - SJD San José del Cabo Los Cabos
ORDSJD
Chicago O'Hare Intl
Sat 11/21
6:29 am-3:00 pm
1 stop9h 31m
San José del Cabo Los Cabos
Thu 11/26
11:15 am-11:44 pm
1 stop11h 29m
$589
ChicagoSan José del Cabo
ORD Chicago O'Hare Intl - SJD San José del Cabo Los Cabos
ORDSJD
Chicago O'Hare Intl
Sat 11/14
2:15 pm-1:44 pm
2 stops24h 29m
San José del Cabo Los Cabos
Sat 11/21
7:58 pm-6:59 pm
2 stops22h 01m
$596
ChicagoSan José del Cabo
ORD Chicago O'Hare Intl - SJD San José del Cabo Los Cabos
ORDSJD
Chicago O'Hare Intl
Thu 10/29
5:46 pm-11:50 am
2 stops20h 04m
San José del Cabo Los Cabos
Thu 11/5
5:10 pm-6:59 pm
2 stops24h 49m
$632
ChicagoSan José del Cabo
MDW Chicago Midway - SJD San José del Cabo Los Cabos
MDWSJD
Chicago Midway
Mon 10/5
6:45 am-12:05 pm
1 stop7h 20m
San José del Cabo Los Cabos
Wed 10/21
1:30 pm-11:15 pm
1 stop7h 45m
$643
ChicagoSan José del Cabo
ORD Chicago O'Hare Intl - SJD San José del Cabo Los Cabos
ORDSJD
Chicago O'Hare Intl
Sat 10/24
5:27 am-11:20 am
1 stop7h 53m
San José del Cabo Los Cabos
Sat 10/31
6:02 am-11:57 pm
2 stops15h 55m
$645
Showing 1-10 of 43 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 August.
| 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 Accuracy3 stars | 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 $477). Flying from Chicago to San José del Cabo in March is currently the most expensive (average of $694). 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 August 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.
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 $384 and $649 in October.The cheapest round-trip price found within the last 5 days was $349 on Volaris (Oct 19-Oct 23).
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 August 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.
Entertainment
7.5
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
8.0
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
8.0
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
8.0
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
8.0
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
8.0
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
8.0
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
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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 August 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 August 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 August 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 August 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$185 | Average$393 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$418 | Average$653 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$435 | Average$663 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$475 | Average$696 | FlexibilityNo cancel fee | On-time63% |