$114+ 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 11/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJD
Aug 29 — Sep 51
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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Best
Last-minute
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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 July 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 July 30, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/26. 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.
Wed 10/217:35 am
ORD
- SJD
1 stop13h 29m
Multiple Airlines
Wed 10/2812:36 pm
SJD
- ORD
2 stops33h 23m
Multiple Airlines
Deal found 7/26![Multiple Airlines logo]()
$348
This Super.com deal was found by Cheapflights users on 7/26. 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 8/242:53 am
ORD
- SJD
1 stop10h 36m
Volaris
Tue 9/112:06 pm
SJD
- ORD
1 stop10h 49m
Volaris
Deal found 7/26![Volaris logo]()
$349
This Super.com deal was found by Cheapflights users on 7/29. 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.
Sat 9/197:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Thu 9/247:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 7/29![Volaris logo]()
$350
This Viva deal was found by Cheapflights users on 7/27. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/172:40 pm
ORD
- SJD
1 stop19h 03m
Viva
Sat 10/241:20 pm
SJD
- ORD
1 stop8h 39m
Viva
Deal found 7/27![Viva logo]()
$351
This Kiwi.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/197:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Sat 10/243:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 7/28![Volaris logo]()
$352
This Super.com deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/187:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Tue 9/223:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 7/26![Volaris logo]()
$353
This Justfly.com deal was found by Cheapflights users on 7/26. 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 Justfly.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
Tue 9/157:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 7/26![Volaris logo]()
$354
This Kiwi.com deal was found by Cheapflights users on 7/29. 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 11/21:19 am
ORD
- SJD
1 stop10h 16m
Volaris
Tue 11/103:36 pm
SJD
- ORD
1 stop7h 03m
Volaris
Deal found 7/29![Volaris logo]()
$355
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 11/21:19 am
ORD
- SJD
1 stop10h 16m
Volaris
Fri 11/1311:16 am
SJD
- ORD
1 stop11h 23m
Volaris
Deal found 7/30![Volaris logo]()
$356
This Kiwi.com deal was found by Cheapflights users on 7/29. 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 11/61:19 am
ORD
- SJD
1 stop10h 16m
Volaris
Fri 11/1311:16 am
SJD
- ORD
1 stop11h 23m
Volaris
Deal found 7/29![Volaris logo]()
$357
This Kiwi.com deal was found by Cheapflights users on 7/28. 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.
Tue 9/12:53 am
ORD
- SJD
1 stop10h 36m
Volaris
Sat 9/53:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 7/28![Volaris logo]()
$358
This Kiwi.com deal was found by Cheapflights users on 7/26. 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.
Sun 10/187:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Fri 10/237:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 7/26![Volaris logo]()
$359
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 July 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 July 30, 2026.
This Volaris deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/187:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Tue 9/2212:02 pm
SJD
- ORD
1 stop9h 45m
Volaris
Deal found 7/25![Volaris logo]()
$448
This United Airlines deal was found by Cheapflights users on 7/25. 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 9/288:52 am
ORD
- SJD
Nonstop4h 33m
United Airlines
Wed 9/3011:52 am
SJD
- ORD
Nonstop4h 15m
United Airlines
Deal found 7/25![United Airlines logo]()
$493
This Delta deal was found by Cheapflights users on 7/27. 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
MDW
- SJD
1 stop7h 02m
Delta
Wed 9/3012:12 pm
SJD
- MDW
1 stop8h 32m
Delta
Deal found 7/27![Delta logo]()
$508
This Alaska Airlines deal was found by Cheapflights users on 7/28. 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.
Fri 9/112:18 pm
ORD
- SJD
2 stops21h 53m
Alaska Airlines
Fri 9/185:50 pm
SJD
- ORD
2 stops23h 31m
Alaska Airlines
Deal found 7/28![Alaska Airlines logo]()
$527
This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/237:10 am
MDW
- SJD
1 stop7h 00m
Southwest
Tue 10/271:30 pm
SJD
- MDW
1 stop7h 40m
Southwest
Deal found 7/29![Southwest logo]()
$543
This Volaris deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/161:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Sat 10/243:36 pm
SJD
- ORD
1 stop7h 19m
Volaris
Deal found 7/28![Volaris logo]()
$455
This Volaris deal was found by Cheapflights users on 7/29. 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.
Sat 9/127:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Sat 9/197:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 7/29![Volaris logo]()
$469
This Delta deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/141:54 am
ORD
- SJD
1 stop12h 54m
Delta
Sun 9/202:27 pm
SJD
- ORD
2 stops16h 03m
Delta
Deal found 7/29![Delta logo]()
$543
This Alaska Airlines deal was found by Cheapflights users on 7/27. 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.
Sat 9/127:20 am
ORD
- SJD
2 stops28h 51m
Alaska Airlines
Sat 9/197:02 pm
SJD
- ORD
2 stops26h 57m
Alaska Airlines
Deal found 7/27![Alaska Airlines logo]()
$552
This Southwest deal was found by Cheapflights users on 7/28. 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 9/115:25 am
MDW
- SJD
1 stop6h 20m
Southwest
Fri 9/1810:40 am
SJD
- MDW
2 stops10h 45m
Southwest
Deal found 7/28![Southwest logo]()
$580
This Delta deal was found by Cheapflights users on 7/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:05 am
MDW
- SJD
2 stops13h 30m
Delta
Fri 10/26:15 am
SJD
- MDW
2 stops14h 29m
Delta
Deal found 7/28![Delta logo]()
$543
This Alaska Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/282:21 pm
ORD
- SJD
1 stop28h 17m
Alaska Airlines
Wed 11/45:03 pm
SJD
- ORD
2 stops24h 57m
Alaska Airlines
Deal found 7/29![Alaska Airlines logo]()
$562
This Southwest deal was found by Cheapflights users on 7/29. 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 10/177:20 am
MDW
- SJD
1 stop7h 30m
Southwest
Sat 10/242:10 pm
SJD
- MDW
1 stop12h 20m
Southwest
Deal found 7/29![Southwest logo]()
$588
This Southwest deal was found by Cheapflights users on 7/26. 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.
Wed 9/96:00 am
MDW
- SJD
2 stops8h 50m
Southwest
Wed 9/1611:40 am
SJD
- MDW
2 stops8h 15m
Southwest
Deal found 7/26![Southwest logo]()
$612
This Delta deal was found by Cheapflights users on 7/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:05 am
MDW
- SJD
2 stops13h 30m
Delta
Fri 9/186:11 am
SJD
- MDW
2 stops14h 33m
Delta
Deal found 7/28![Delta logo]()
$616
This Delta deal was found by Cheapflights users on 7/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/126:05 am
MDW
- SJD
1 stop7h 02m
Delta
Sat 9/1912:12 pm
SJD
- MDW
1 stop8h 32m
Delta
Deal found 7/28![Delta logo]()
$639
This Southwest deal was found by Cheapflights users on 7/29. 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 9/196:35 am
MDW
- SJD
2 stops7h 40m
Southwest
Sat 9/2610:25 am
SJD
- MDW
1 stop9h 40m
Southwest
Deal found 7/29![Southwest logo]()
$645
This Southwest deal was found by Cheapflights users on 7/29. 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 10/247:00 pm
MDW
- SJD
2 stops20h 15m
Southwest
Sat 11/712:15 pm
SJD
- MDW
2 stops16h 25m
Southwest
Deal found 7/29![Southwest logo]()
$645
Last-minute flights from Chicago to San José del CaboDiscover last-minute flight deals from Chicago to San José del Cabo. Data last updated July 30, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to San José del Cabo. Data last updated July 30, 2026 and is based on user searches.
This Mytrip deal was found by Cheapflights users on 7/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/98:23 pm
MDW
- SJD
1 stop13h 53m
Volaris
Sun 8/1612:02 pm
SJD
- MDW
3 stops26h 28m
Volaris
Deal found 7/29![Volaris logo]()
$636
This Delta deal was found by Cheapflights users on 7/27. 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.
Sun 8/96:05 am
MDW
- SJD
1 stop7h 02m
Delta
Wed 8/1912:12 pm
SJD
- MDW
1 stop8h 24m
Delta
Deal found 7/27![Delta logo]()
$656
This FlightHub deal was found by Cheapflights users on 7/28. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/191:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Sat 8/293:36 pm
SJD
- ORD
1 stop11h 05m
Volaris
Deal found 7/28![Volaris logo]()
$370
This Super.com deal was found by Cheapflights users on 7/27. 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 8/217:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Fri 8/287:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 7/27![Volaris logo]()
$357
This Super.com deal was found by Cheapflights users on 7/26. 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 8/221:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Sun 8/307:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 7/26![Volaris logo]()
$364
This Super.com deal was found by Cheapflights users on 7/30. 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 8/221:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Tue 8/2512:06 pm
SJD
- ORD
1 stop10h 49m
Volaris
Deal found 7/30![Volaris logo]()
$377
This FlightHub deal was found by Cheapflights users on 7/27. 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 8/247:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Mon 8/317:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 7/27![Volaris logo]()
$348
This Super.com deal was found by Cheapflights users on 7/26. 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 8/242:53 am
ORD
- SJD
1 stop10h 36m
Volaris
Tue 9/112:06 pm
SJD
- ORD
1 stop10h 49m
Volaris
Deal found 7/26![Volaris logo]()
$349
This Kiwi.com deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/267:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Wed 9/27:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 7/27![Volaris logo]()
$352
This Super.com deal was found by Cheapflights users on 7/29. 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.
Wed 8/261:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Sun 8/307:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 7/29![Volaris logo]()
$354
This Super.com deal was found by Cheapflights users on 7/30. 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.
Thu 8/271:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Thu 9/312:02 pm
SJD
- ORD
1 stop9h 45m
Volaris
Deal found 7/30![Volaris logo]()
$356
This Kiwi.com deal was found by Cheapflights users on 7/30. 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.
Fri 8/281:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Tue 9/17:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 7/30![Volaris logo]()
$375
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 July 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 July 30, 2026.
This Booking.com deal was found by Cheapflights users on 7/28. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/412:35 am
ORD
- SJD
1 stop21h 15m
Viva
Deal found 7/28![Viva logo]()
$114
This Booking.com deal was found by Cheapflights users on 7/27. 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 1/1312:30 am
ORD
- SJD
1 stop18h 09m
Viva
Deal found 7/27![Viva logo]()
$121
This Booking.com deal was found by Cheapflights users on 7/27. 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 1/2012:30 am
ORD
- SJD
1 stop8h 05m
Viva
Deal found 7/27![Viva logo]()
$123
This Booking.com deal was found by Cheapflights users on 7/26. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/195:20 pm
ORD
- SJD
1 stop16h 23m
Viva
Deal found 7/26![Viva logo]()
$127
This Super.com deal was found by Cheapflights users on 7/28. 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.
Tue 8/112:53 am
ORD
- SJD
1 stop7h 23m
Volaris
Deal found 7/28![Volaris logo]()
$129
This Super.com deal was found by Cheapflights users on 7/29. 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 9/287:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Deal found 7/29![Volaris logo]()
$130
This Viva deal was found by Cheapflights users on 7/26. 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 Viva is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/2412:30 am
ORD
- SJD
1 stop8h 05m
Viva
Deal found 7/26![Viva logo]()
$132
This Booking.com deal was found by Cheapflights users on 7/27. 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.
Fri 1/1512:30 am
ORD
- SJD
1 stop8h 05m
Viva
Deal found 7/27![Viva logo]()
$133
This Super.com deal was found by Cheapflights users on 7/27. 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.
Mon 10/267:29 am
ORD
- SJD
1 stop9h 31m
Volaris
Deal found 7/27![Volaris logo]()
$135
This Super.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/261:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Deal found 7/28![Volaris logo]()
$136
This Kiwi.com deal was found by Cheapflights users on 7/29. 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.
Sat 9/267:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Deal found 7/29![Volaris logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 7/25. 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.
Sat 9/57:30 pm
MDW
- SJD
2 stops25h 53m
Multiple Airlines
Deal found 7/25![Multiple Airlines logo]()
$214
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 July 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $348 (Kiwi.com) |
One-way from | $114 (Booking.com) |
Popular in | March |
Cheapest in | September |
Average price | $608 |
Good round-trip deal | $659 or less |
Good one-way deal | $295 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 July 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 - SJD
ORDSJD
Chicago O'Hare Intl
Fri 9/18
7:35 am-7:04 pm
1 stop13h 29m
San José del Cabo Los Cabos
Tue 9/22
12:02 pm-11:47 pm
1 stop9h 45m
$448
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Fri 10/16
1:40 am-10:09 am
1 stop10h 29m
San José del Cabo Los Cabos
Sat 10/24
3:36 pm-12:55 am
1 stop7h 19m
$455
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Sat 9/12
7:35 am-7:04 pm
1 stop13h 29m
San José del Cabo Los Cabos
Sat 9/19
7:47 pm-5:52 am
1 stop8h 05m
$469
Quickest round-trip
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Mon 9/28
8:52 am-11:25 am
Nonstop4h 33m
San José del Cabo Los Cabos
Wed 9/30
11:52 am-6:07 pm
Nonstop4h 15m
$493
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Mon 9/28
6:05 am-11:07 am
1 stop7h 02m
San José del Cabo Los Cabos
Wed 9/30
12:12 pm-10:44 pm
1 stop8h 32m
$508
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Fri 9/11
2:18 pm-10:11 am
2 stops21h 53m
San José del Cabo Los Cabos
Fri 9/18
5:50 pm-7:21 pm
2 stops23h 31m
$527
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Fri 10/23
7:10 am-12:10 pm
1 stop7h 00m
San José del Cabo Los Cabos
Tue 10/27
1:30 pm-11:10 pm
1 stop7h 40m
$543
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Mon 9/14
1:54 am-12:48 pm
1 stop12h 54m
San José del Cabo Los Cabos
Sun 9/20
2:27 pm-8:30 am
2 stops16h 03m
$543
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Fri 9/25
6:05 am-5:35 pm
2 stops13h 30m
San José del Cabo Los Cabos
Fri 10/2
6:15 am-10:44 pm
2 stops14h 29m
$543
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Sat 9/12
7:20 am-10:11 am
2 stops28h 51m
San José del Cabo Los Cabos
Sat 9/19
7:02 pm-11:59 pm
2 stops26h 57m
$552
Showing 1-10 of 37 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 July.
| 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 $486). Flying from Chicago to San José del Cabo in March is currently the most expensive (average of $691). 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 July 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 $476 and $693 in October.The cheapest round-trip price found within the last 5 days was $348 on Multiple Airlines (Oct 20-Oct 24).
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.
Mexico City (MEX) – chosen by Cheapflights users on 71% 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.
Mexico City (MEX) is the most affordable 1-stop option, with an average round-trip price of $383.
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 July 30, 2026.
Peruse reviews from past customers who have flown with Southwest,United Airlines, andAmerican Airlines from Chicago to San José del Cabo to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
7.0
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
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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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 July 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 July 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 July 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 2,558,603 searches. Data last updated July 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$185 | Average$393 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$417 | Average$650 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$439 | Average$655 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$475 | Average$696 | FlexibilityNo cancel fee | On-time63% |