$99+ 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 9/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJD
Jul 4 — Jul 111
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 41 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 June 4, 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 June 4, 2026.
This Super.com deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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 6/227:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Thu 6/2512:02 pm
SJD
- ORD
1 stop9h 45m
Volaris
Deal found 6/1![Volaris logo]()
$382
This Super.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 6/192:53 am
ORD
- SJD
1 stop10h 36m
Volaris
Tue 6/237:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 6/3![Volaris logo]()
$383
This Super.com deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 7/67:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Thu 7/93:36 pm
SJD
- ORD
1 stop11h 05m
Volaris
Deal found 6/2![Volaris logo]()
$384
This FlightHub deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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 6/163:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 6/1![Volaris logo]()
$385
This Kiwi.com deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 6/27:35 am
ORD
- SJD
1 stop13h 29m
Multiple Airlines
Tue 6/98:00 am
SJD
- ORD
2 stops14h 55m
Multiple Airlines
Deal found 5/30![Multiple Airlines logo]()
$386
This FlightHub deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 6/151:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Sat 6/207:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 5/30![Volaris logo]()
$387
This Gotogate deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/261:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Sun 11/14:08 pm
SJD
- ORD
1 stop11h 28m
Volaris
Deal found 5/30![Volaris logo]()
$388
This FlightHub deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 6/161:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Sun 6/217:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 5/30![Volaris logo]()
$389
This Super.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 6/274:03 am
ORD
- SJD
1 stop9h 26m
Volaris
Sat 7/412:02 pm
SJD
- ORD
1 stop9h 45m
Volaris
Deal found 6/3![Volaris logo]()
$391
This Kiwi.com deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 6/37:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Wed 6/102:02 pm
SJD
- ORD
2 stops32h 53m
Volaris
Deal found 5/30![Volaris logo]()
$392
This Volaris deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 10/257:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Sat 10/3112:02 pm
SJD
- ORD
1 stop9h 45m
Volaris
Deal found 6/2![Volaris logo]()
$393
This Kiwi.com deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 7/62:53 am
ORD
- SJD
1 stop10h 36m
Multiple Airlines
Fri 7/108:05 am
SJD
- ORD
2 stops14h 50m
Multiple Airlines
Deal found 5/30![Multiple Airlines logo]()
$394
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 June 4, 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 June 4, 2026.
This Volaris deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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 7/17:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Wed 7/83:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 5/31![Volaris logo]()
$472
This Alaska Airlines deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 7/307:59 pm
ORD
- SJD
1 stop18h 58m
Alaska Airlines
Tue 8/411:21 am
SJD
- ORD
1 stop16h 59m
Alaska Airlines
Deal found 5/30![Alaska Airlines logo]()
$588
This Delta deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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 11/1911:57 am
SJD
- MDW
1 stop8h 48m
Delta
Deal found 5/31![Delta logo]()
$614
This Southwest deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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 11/65:10 am
MDW
- SJD
1 stop7h 30m
Southwest
Fri 11/62:05 pm
SJD
- MDW
1 stop10h 00m
Southwest
Deal found 5/31![Southwest logo]()
$639
This Volaris deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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 6/111:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Mon 6/157:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 5/31![Volaris logo]()
$572
This Alaska Airlines deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 7/102:20 pm
ORD
- SJD
2 stops21h 51m
Alaska Airlines
Wed 7/152:07 pm
SJD
- ORD
1 stop21h 14m
Alaska Airlines
Deal found 5/30![Alaska Airlines logo]()
$606
This Delta deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 7/288:03 am
ORD
- SJD
2 stops16h 27m
Delta
Fri 8/712:12 pm
SJD
- ORD
1 stop9h 50m
Delta
Deal found 6/3![Delta logo]()
$624
This Southwest deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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 7/17:00 am
MDW
- SJD
1 stop7h 55m
Southwest
Wed 7/810:40 am
SJD
- MDW
1 stop8h 05m
Southwest
Deal found 5/31![Southwest logo]()
$643
This Volaris deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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.
Mon 6/157:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Mon 6/223:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 6/2![Volaris logo]()
$599
This Delta deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 7/76:00 am
MDW
- SJD
1 stop7h 11m
Delta
Tue 7/1412:16 pm
SJD
- MDW
1 stop7h 59m
Delta
Deal found 6/3![Delta logo]()
$624
This Southwest deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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 11/309:30 pm
MDW
- SJD
2 stops15h 10m
Southwest
Sun 12/611:50 am
SJD
- MDW
2 stops9h 50m
Southwest
Deal found 6/1![Southwest logo]()
$673
This Delta deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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
Sun 8/1612:12 pm
SJD
- MDW
1 stop8h 24m
Delta
Deal found 5/31![Delta logo]()
$639
This Southwest deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 7/235:15 am
MDW
- SJD
2 stops10h 25m
Southwest
Tue 7/2811:35 am
SJD
- MDW
2 stops10h 35m
Southwest
Deal found 6/3![Southwest logo]()
$673
This Delta deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 9/1010:35 am
MDW
- SJD
2 stops13h 52m
Delta
Wed 9/1612:15 pm
SJD
- MDW
1 stop8h 10m
Delta
Deal found 6/2![Delta logo]()
$640
This Delta deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 8/96:05 am
MDW
- SJD
1 stop7h 02m
Delta
Sun 8/1612:12 pm
SJD
- MDW
1 stop8h 24m
Delta
Deal found 5/30![Delta logo]()
$668
This Delta deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 10/46:05 am
MDW
- SJD
1 stop7h 05m
Delta
Sat 10/1011:57 am
SJD
- MDW
1 stop7h 48m
Delta
Deal found 5/30![Delta logo]()
$668
This Delta deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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 7/106:00 am
MDW
- SJD
2 stops14h 35m
Delta
Wed 7/1512:16 pm
SJD
- MDW
1 stop7h 59m
Delta
Deal found 5/31![Delta logo]()
$668
This Delta deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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 9/126:00 am
MDW
- SJD
2 stops14h 33m
Delta
Sat 9/196:15 am
SJD
- MDW
2 stops14h 10m
Delta
Deal found 6/1![Delta logo]()
$694
Last-minute flights from Chicago to San José del CaboDiscover last-minute flight deals from Chicago to San José del Cabo. Data last updated June 4, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to San José del Cabo. Data last updated June 4, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 6/107:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Sun 6/147:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 5/30![Volaris logo]()
$391
This FlightHub deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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 6/163:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 6/1![Volaris logo]()
$385
This Super.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 6/112:53 am
ORD
- SJD
1 stop10h 36m
Volaris
Sat 6/2012:02 pm
SJD
- ORD
1 stop9h 45m
Volaris
Deal found 6/3![Volaris logo]()
$406
This FlightHub deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 6/121:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Wed 6/173:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 6/3![Volaris logo]()
$386
This Super.com deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 6/132:53 am
ORD
- SJD
1 stop10h 36m
Volaris
Sun 6/217:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 5/30![Volaris logo]()
$396
This Kiwi.com deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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 6/228:23 pm
MDW
- SJD
1 stop17h 06m
Multiple Airlines
Fri 6/267:50 pm
SJD
- MDW
3 stops20h 15m
Multiple Airlines
Deal found 5/31![Multiple Airlines logo]()
$602
This Southwest deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 6/296:40 am
MDW
- SJD
1 stop9h 45m
Southwest
Tue 7/73:15 pm
SJD
- MDW
1 stop6h 55m
Southwest
Deal found 5/30![Southwest logo]()
$643
This Delta deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 7/66:00 am
MDW
- SJD
1 stop7h 25m
Delta
Tue 7/1412:16 pm
SJD
- MDW
1 stop7h 59m
Delta
Deal found 6/2![Delta logo]()
$644
This Delta deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 7/76:00 am
MDW
- SJD
1 stop7h 11m
Delta
Fri 7/1012:16 pm
SJD
- MDW
1 stop7h 59m
Delta
Deal found 6/3![Delta logo]()
$624
This Kiwi.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 7/108:23 pm
MDW
- SJD
1 stop13h 53m
Multiple Airlines
Tue 7/147:47 pm
SJD
- MDW
2 stops18h 03m
Multiple Airlines
Deal found 6/3![Multiple Airlines logo]()
$588
This Kiwi.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 7/188:49 pm
MDW
- SJD
1 stop13h 27m
Volaris
Sat 7/257:47 pm
SJD
- MDW
2 stops22h 45m
Volaris
Deal found 6/3![Volaris logo]()
$620
This Gotogate deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 7/238:49 pm
MDW
- SJD
1 stop13h 27m
Volaris
Mon 7/278:50 am
SJD
- MDW
1 stop8h 14m
Volaris
Deal found 6/2![Volaris logo]()
$604
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 June 4, 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 June 4, 2026.
This Super.com deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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 9/117:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Deal found 5/31![Volaris logo]()
$99
This Super.com deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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 8/287:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Deal found 5/31![Volaris logo]()
$101
This Kiwi.com deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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 8/247:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Deal found 5/31![Volaris logo]()
$106
This Kiwi.com deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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 8/251:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Deal found 5/31![Volaris logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 9/17:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Deal found 6/3![Volaris logo]()
$110
This Super.com deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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 8/277:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Deal found 5/31![Volaris logo]()
$119
This Mytrip deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/142:53 am
ORD
- SJD
1 stop7h 23m
Volaris
Deal found 6/1![Volaris logo]()
$120
This Super.com deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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 6/267:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Deal found 5/31![Volaris logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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 8/292:53 am
ORD
- SJD
1 stop10h 36m
Volaris
Deal found 6/1![Volaris logo]()
$125
This Trip.com deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/238:49 pm
MDW
- SJD
1 stop13h 27m
Volaris
Deal found 6/2![Volaris logo]()
$174
This Mytrip deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/158:49 pm
MDW
- SJD
1 stop13h 27m
Volaris
Deal found 6/1![Volaris logo]()
$190
This Trip.com deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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.
Sat 7/258:49 pm
MDW
- SJD
1 stop13h 27m
Volaris
Deal found 5/31![Volaris logo]()
$193
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 June 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $382 (Super.com) |
One-way from | $99 (Super.com) |
Popular in | March |
Cheapest in | September |
Average price | $602 |
Good round-trip deal | $632 or less |
Good one-way deal | $335 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 June 4, 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 7/1
7:35 am-7:04 pm
1 stop13h 29m
San José del Cabo Los Cabos
Wed 7/8
3:36 pm-12:55 am
1 stop7h 19m
$472
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Thu 6/11
1:40 am-10:09 am
1 stop10h 29m
San José del Cabo Los Cabos
Mon 6/15
7:47 pm-5:52 am
1 stop8h 05m
$572
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Thu 7/30
7:59 pm-12:57 pm
1 stop18h 58m
San José del Cabo Los Cabos
Tue 8/4
11:21 am-6:20 am
1 stop16h 59m
$588
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Mon 6/15
7:35 am-7:04 pm
1 stop13h 29m
San José del Cabo Los Cabos
Mon 6/22
3:36 pm-12:55 am
1 stop7h 19m
$599
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Fri 7/10
2:20 pm-10:11 am
2 stops21h 51m
San José del Cabo Los Cabos
Wed 7/15
2:07 pm-1:21 pm
1 stop21h 14m
$606
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Mon 11/9
6:00 am-12:25 pm
1 stop7h 25m
San José del Cabo Los Cabos
Thu 11/19
11:57 am-9:45 pm
1 stop8h 48m
$614
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Tue 7/28
8:03 am-10:30 pm
2 stops16h 27m
San José del Cabo Los Cabos
Fri 8/7
12:12 pm-12:02 am
1 stop9h 50m
$624
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Tue 7/7
6:00 am-11:11 am
1 stop7h 11m
San José del Cabo Los Cabos
Tue 7/14
12:16 pm-10:15 pm
1 stop7h 59m
$624
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Fri 11/6
5:10 am-11:40 am
1 stop7h 30m
San José del Cabo Los Cabos
Fri 11/6
2:05 pm-1:05 am
1 stop10h 00m
$639
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Wed 8/12
6:05 am-11:07 am
1 stop7h 02m
San José del Cabo Los Cabos
Sun 8/16
12:12 pm-10:36 pm
1 stop8h 24m
$639
Showing 1-10 of 39 resultsSorted by cheapest first
Compare providers for flights from Chicago to San José del Cabo
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to San José del Cabo in June.
| 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
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 $1,134). 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 June 4, 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.
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 June 4, 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.
Comfort
8.0
Crew
8.6
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Comfort
8.0
Crew
8.6
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Comfort
8.0
Crew
8.6
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Comfort
8.0
Crew
8.6
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Comfort
8.0
Crew
8.6
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Comfort
8.0
Crew
8.6
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
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 June 4, 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 June 4, 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 June 4, 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 2,558,603 searches. Data last updated June 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$185 | Average$391 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$416 | Average$632 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$416 | Average$637 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$475 | Average$695 | FlexibilityNo cancel fee | On-time63% |