$121+ 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 6/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJD
Jun 15 — Jun 221
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 August, booked 61 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 May 16, 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 May 16, 2026.
This Super.com deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 5/271:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Thu 5/283:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 5/11![Volaris logo]()
$386
This FlightHub deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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.
Thu 6/117:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Tue 6/167:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 5/12![Volaris logo]()
$387
This FlightHub deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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.
Sat 6/272:53 am
ORD
- SJD
1 stop10h 36m
Volaris
Wed 7/13:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 5/13![Volaris logo]()
$388
This FlightHub deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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.
Thu 6/187:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Mon 6/2212:02 pm
SJD
- ORD
1 stop9h 45m
Volaris
Deal found 5/11![Volaris logo]()
$389
This Super.com deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/232:53 am
ORD
- SJD
1 stop10h 36m
Volaris
Sat 6/2712:02 pm
SJD
- ORD
1 stop9h 45m
Volaris
Deal found 5/13![Volaris logo]()
$390
This FlightHub deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 7/132:53 am
ORD
- SJD
1 stop10h 36m
Volaris
Mon 7/203:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 5/11![Volaris logo]()
$391
This FlightHub deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 5/157:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Wed 5/2012:02 pm
SJD
- ORD
1 stop9h 45m
Volaris
Deal found 5/11![Volaris logo]()
$392
This Kiwi.com deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 6/31:40 am
ORD
- SJD
1 stop10h 29m
Multiple Airlines
Sun 6/78:20 am
SJD
- ORD
1 stop13h 35m
Multiple Airlines
Deal found 5/12![Multiple Airlines logo]()
$393
This Super.com deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 6/287:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Sat 7/412:06 pm
SJD
- ORD
1 stop10h 49m
Volaris
Deal found 5/11![Volaris logo]()
$394
This Justfly.com deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” 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.
Sat 6/137:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Wed 6/1712:02 pm
SJD
- ORD
1 stop9h 45m
Volaris
Deal found 5/15![Volaris logo]()
$395
This Kiwi.com deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 7/56:21 am
ORD
- SJD
1 stop7h 08m
Multiple Airlines
Fri 7/101:10 pm
SJD
- ORD
2 stops8h 45m
Multiple Airlines
Deal found 5/14![Multiple Airlines logo]()
$397
This Viva deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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.
Thu 8/2712:25 pm
ORD
- SJD
1 stop26h 00m
Viva
Sun 8/301:10 pm
SJD
- ORD
1 stop8h 45m
Viva
Deal found 5/11![Viva logo]()
$398
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 May 16, 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 May 16, 2026.
This Volaris deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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 8/121:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Sun 8/167:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 5/10![Volaris logo]()
$478
This Delta deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 8/216:05 am
MDW
- SJD
1 stop7h 02m
Delta
Fri 8/286:04 am
SJD
- MDW
2 stops14h 32m
Delta
Deal found 5/13![Delta logo]()
$564
This Alaska Airlines deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 6/276:20 am
ORD
- SJD
1 stop10h 19m
Alaska Airlines
Fri 7/310:45 am
SJD
- ORD
1 stop10h 51m
Alaska Airlines
Deal found 5/13![Alaska Airlines logo]()
$564
This Southwest deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” 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 9/68:50 pm
MDW
- SJD
2 stops18h 00m
Southwest
Sun 9/1311:40 am
SJD
- MDW
2 stops16h 00m
Southwest
Deal found 5/15![Southwest logo]()
$683
This Volaris deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 6/21:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Mon 6/87:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 5/14![Volaris logo]()
$512
This Delta deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 8/710:07 am
ORD
- SJD
2 stops14h 23m
Delta
Fri 8/146:04 am
SJD
- ORD
2 stops15h 54m
Delta
Deal found 5/13![Delta logo]()
$564
This Volaris deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” 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 7/192:53 am
ORD
- SJD
1 stop7h 23m
Volaris
Mon 7/273:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 5/15![Volaris logo]()
$516
This Alaska Airlines deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” 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 7/186:20 am
ORD
- SJD
1 stop10h 19m
Alaska Airlines
Thu 7/2310:45 am
SJD
- ORD
1 stop10h 51m
Alaska Airlines
Deal found 5/15![Alaska Airlines logo]()
$574
This Delta deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 8/126:05 am
MDW
- SJD
2 stops14h 37m
Delta
Sun 8/162:44 pm
SJD
- MDW
2 stops15h 56m
Delta
Deal found 5/12![Delta logo]()
$569
This Alaska Airlines deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 7/185:59 pm
ORD
- SJD
2 stops18h 12m
Alaska Airlines
Sat 7/2510:45 am
SJD
- ORD
1 stop24h 36m
Alaska Airlines
Deal found 5/13![Alaska Airlines logo]()
$583
This Volaris deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/272:53 am
ORD
- SJD
1 stop10h 36m
Volaris
Fri 7/33:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 5/13![Volaris logo]()
$533
This Delta deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 8/128:02 am
ORD
- SJD
2 stops12h 40m
Delta
Sun 8/162:44 pm
SJD
- ORD
2 stops15h 12m
Delta
Deal found 5/12![Delta logo]()
$569
This Southwest deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” 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 9/185:55 am
MDW
- SJD
1 stop8h 55m
Southwest
Sun 9/272:05 pm
SJD
- MDW
1 stop8h 20m
Southwest
Deal found 5/15![Southwest logo]()
$703
This Volaris deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 7/12:53 am
ORD
- SJD
1 stop7h 23m
Volaris
Sun 7/57:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 5/12![Volaris logo]()
$561
This Southwest deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 10/155:10 am
MDW
- SJD
2 stops10h 30m
Southwest
Sun 10/182:00 pm
SJD
- MDW
1 stop12h 30m
Southwest
Deal found 5/14![Southwest logo]()
$713
This Delta deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 8/126:05 am
MDW
- SJD
1 stop7h 02m
Delta
Mon 8/172:44 pm
SJD
- MDW
2 stops15h 56m
Delta
Deal found 5/12![Delta logo]()
$596
This Volaris deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” 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 6/31:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Sun 6/77:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 5/15![Volaris logo]()
$562
This Delta deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 8/156:05 am
MDW
- SJD
2 stops11h 03m
Delta
Sat 8/2212:12 pm
SJD
- MDW
1 stop8h 24m
Delta
Deal found 5/13![Delta logo]()
$609
This Volaris deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 6/232:53 am
ORD
- SJD
1 stop10h 36m
Volaris
Sun 6/2812:02 pm
SJD
- ORD
1 stop9h 45m
Volaris
Deal found 5/13![Volaris logo]()
$588
This Delta deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 11/96:00 am
MDW
- SJD
1 stop7h 25m
Delta
Thu 11/196:05 am
SJD
- MDW
2 stops14h 40m
Delta
Deal found 5/12![Delta logo]()
$643
This Delta deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 10/1710:35 am
MDW
- SJD
2 stops13h 53m
Delta
Sat 10/246:04 am
SJD
- MDW
2 stops13h 41m
Delta
Deal found 5/14![Delta logo]()
$693
This Delta deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” 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 9/66:00 am
MDW
- SJD
1 stop7h 22m
Delta
Sun 9/1312:15 pm
SJD
- MDW
1 stop7h 31m
Delta
Deal found 5/15![Delta logo]()
$705
Last-minute flights from Chicago to San José del CaboDiscover last-minute flight deals from Chicago to San José del Cabo. Data last updated May 16, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to San José del Cabo. Data last updated May 16, 2026 and is based on user searches.
This FlightHub deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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.
Tue 5/192:35 am
ORD
- SJD
1 stop10h 57m
Volaris
Wed 5/2712:02 pm
SJD
- ORD
1 stop9h 45m
Volaris
Deal found 5/12![Volaris logo]()
$408
This Super.com deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 5/192:35 am
ORD
- SJD
1 stop10h 57m
Volaris
Tue 5/2612:06 pm
SJD
- ORD
1 stop10h 49m
Volaris
Deal found 5/11![Volaris logo]()
$430
This FlightHub deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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.
Tue 5/192:35 am
ORD
- SJD
1 stop10h 57m
Volaris
Sun 5/2412:06 pm
SJD
- ORD
1 stop10h 49m
Volaris
Deal found 5/11![Volaris logo]()
$496
This Kiwi.com deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 5/201:40 am
ORD
- SJD
1 stop10h 29m
Multiple Airlines
Thu 5/281:05 pm
SJD
- ORD
1 stop8h 40m
Multiple Airlines
Deal found 5/12![Multiple Airlines logo]()
$478
This Kiwi.com deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 5/201:40 am
ORD
- SJD
1 stop10h 29m
Multiple Airlines
Mon 5/258:40 am
SJD
- ORD
1 stop14h 05m
Multiple Airlines
Deal found 5/12![Multiple Airlines logo]()
$479
This Kiwi.com deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 5/208:23 pm
MDW
- SJD
1 stop11h 52m
Multiple Airlines
Tue 5/267:47 pm
SJD
- MDW
2 stops21h 17m
Multiple Airlines
Deal found 5/11![Multiple Airlines logo]()
$579
This FlightHub deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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.
Thu 5/217:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Tue 5/2612:06 pm
SJD
- ORD
1 stop10h 49m
Volaris
Deal found 5/13![Volaris logo]()
$429
This Gotogate deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/217:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Sun 5/3112:02 pm
SJD
- ORD
1 stop9h 45m
Volaris
Deal found 5/12![Volaris logo]()
$468
This Super.com deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 5/217:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Sun 5/2412:06 pm
SJD
- ORD
1 stop10h 49m
Volaris
Deal found 5/13![Volaris logo]()
$502
This FlightHub deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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.
Sat 5/237:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Tue 5/2612:06 pm
SJD
- ORD
1 stop10h 49m
Volaris
Deal found 5/13![Volaris logo]()
$495
This Mytrip deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/48:49 pm
MDW
- SJD
1 stop16h 40m
Volaris
Sun 6/77:37 pm
SJD
- MDW
2 stops21h 27m
Volaris
Deal found 5/12![Volaris logo]()
$632
This Kiwi.com deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 6/118:49 pm
MDW
- SJD
1 stop17h 41m
Multiple Airlines
Sun 6/146:50 am
SJD
- MDW
1 stop10h 14m
Multiple Airlines
Deal found 5/12![Multiple Airlines logo]()
$631
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 May 16, 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 May 16, 2026.
This Super.com deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/161:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Deal found 5/11![Volaris logo]()
$121
This Kiwi.com deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 6/202:53 am
ORD
- SJD
1 stop10h 36m
Volaris
Deal found 5/13![Volaris logo]()
$124
This Kiwi.com deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 7/56:21 am
ORD
- SJD
1 stop7h 08m
Volaris
Deal found 5/13![Volaris logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 7/36:21 am
ORD
- SJD
1 stop10h 30m
Volaris
Deal found 5/11![Volaris logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 7/106:21 am
ORD
- SJD
1 stop7h 08m
Volaris
Deal found 5/13![Volaris logo]()
$131
This Super.com deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 10/237:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Deal found 5/13![Volaris logo]()
$132
This Super.com deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/222:53 am
ORD
- SJD
1 stop10h 36m
Volaris
Deal found 5/11![Volaris logo]()
$135
This Super.com deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/241:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Deal found 5/12![Volaris logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” 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 6/92:53 am
ORD
- SJD
1 stop10h 36m
Volaris
Deal found 5/15![Volaris logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 6/101:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Deal found 5/14![Volaris logo]()
$140
This Super.com deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” 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 7/218:49 pm
MDW
- SJD
1 stop13h 27m
Volaris
Deal found 5/15![Volaris logo]()
$153
This Trip.com deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 7/288:49 pm
MDW
- SJD
1 stop13h 27m
Volaris
Deal found 5/14![Volaris logo]()
$215
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 May 16, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $386 (Super.com) |
One-way from | $121 (Super.com) |
Popular in | March |
Cheapest in | September |
Average price | $616 |
Good round-trip deal | $627 or less |
Good one-way deal | $364 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 2,558,603 searches. Data last updated May 16, 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 - SJD
ORDSJD
Chicago O'Hare Intl
Wed 8/12
1:40 am-10:09 am
1 stop10h 29m
San José del Cabo Los Cabos
Sun 8/16
7:47 pm-5:52 am
1 stop8h 05m
$478
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Tue 6/2
1:40 am-10:09 am
1 stop10h 29m
San José del Cabo Los Cabos
Mon 6/8
7:47 pm-5:52 am
1 stop8h 05m
$512
Quickest round-trip
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Sun 7/19
2:53 am-8:16 am
1 stop7h 23m
San José del Cabo Los Cabos
Mon 7/27
3:36 pm-12:55 am
1 stop7h 19m
$516
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Sat 6/27
2:53 am-11:29 am
1 stop10h 36m
San José del Cabo Los Cabos
Fri 7/3
3:36 pm-12:55 am
1 stop7h 19m
$533
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Wed 7/1
2:53 am-8:16 am
1 stop7h 23m
San José del Cabo Los Cabos
Sun 7/5
7:47 pm-5:52 am
1 stop8h 05m
$561
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Wed 6/3
1:40 am-10:09 am
1 stop10h 29m
San José del Cabo Los Cabos
Sun 6/7
7:47 pm-5:52 am
1 stop8h 05m
$562
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Fri 8/21
6:05 am-11:07 am
1 stop7h 02m
San José del Cabo Los Cabos
Fri 8/28
6:04 am-10:36 pm
2 stops14h 32m
$564
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Sat 6/27
6:20 am-2:39 pm
1 stop10h 19m
San José del Cabo Los Cabos
Fri 7/3
10:45 am-11:36 pm
1 stop10h 51m
$564
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Fri 8/7
10:07 am-10:30 pm
2 stops14h 23m
San José del Cabo Los Cabos
Fri 8/14
6:04 am-11:58 pm
2 stops15h 54m
$564
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Wed 8/12
6:05 am-6:42 pm
2 stops14h 37m
San José del Cabo Los Cabos
Sun 8/16
2:44 pm-8:40 am
2 stops15h 56m
$569
Showing 1-10 of 42 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 May.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 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
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.
What is the cheapest month to book a flight from Chicago to San José del Cabo?
Currently, February is the cheapest month in which you can book a flight from Chicago to San José del Cabo (average of $131). Flying from Chicago to San José del Cabo in March is currently the most expensive (average of $1,184). 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 May 16, 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?
What’s the top layover airport for flights from Chicago to San José del Cabo?
Share of 1-stop round-trip flights from Chicago to San José del Cabo chosen by Cheapflights users in the past 12 months, using the same layover each way.
Houston (IAH) – chosen by Cheapflights users on 67% of 1-stop itineraries from Chicago to San José del Cabo on Cheapflights.
What’s the cheapest layover airport for flights from Chicago to San José del Cabo?
Average round-trip fare for 1-stop flights from Chicago to San José del Cabo, chosen by Cheapflights users in the past 12 months, with the same layover each way.
Houston (IAH) is the most affordable 1-stop option, with an average round-trip price of $607.
What’s the fastest layover option from Chicago to San José del Cabo?
Shortest average travel time for 1-stop one-way flights from Chicago to San José del Cabo, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.
Flights via Houston (IAH) have the shortest average one-way travel time for 1-stop routes: 6h 30m.
Which airport typically offers the quickest layover for flights from Chicago to San José del Cabo?
Average layover duration for 1-stop one-way flights from Chicago to San José del Cabo, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.
Flights via Houston (IAH) offer the fastest connection on this route, with an average layover time of 1h 09m.
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 May 16, 2026.
Peruse reviews from past customers who have flown with Southwest,Delta, andUnited 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.
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Overall
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Overall
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Overall
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Overall
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Overall
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Overall
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from Chicago to 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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Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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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 May 16, 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 May 16, 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 May 16, 2026.
Top 6 airlines flying from Chicago to San José del Cabo
Discover the top 6 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 2,558,603 searches. Data last updated May 16, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$184 | Average$543 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$185 | Average$390 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$318 | Average$470 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$413 | Average$624 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$415 | Average$629 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$475 | Average$695 | FlexibilityNo cancel fee | On-time63% |