$90+ 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 4/26. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJD
Apr 4 — Apr 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 July, 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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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 March 5, 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 March 5, 2026.
This Mytrip deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” 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.
Wed 6/171:59 am
ORD
- SJD
3 stops19h 05m
Volaris
Mon 6/227:47 pm
SJD
- ORD
1 stop8h 05m
Volaris
Deal found 3/4![Volaris logo]()
$453
This Kiwi.com deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” 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 5/301:40 am
ORD
- SJD
2 stops12h 45m
Multiple Airlines
Thu 6/49:00 am
SJD
- ORD
2 stops12h 45m
Multiple Airlines
Deal found 3/4![Multiple Airlines logo]()
$455
This Expedia deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/229:16 pm
MDW
- SJD
1 stop15h 20m
Frontier
Sat 5/3011:58 am
SJD
- MDW
1 stop17h 02m
Frontier
Deal found 3/4![Frontier logo]()
$455
This Delta deal was found by Cheapflights users on 3/2. 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 4/279:48 am
ORD
- SJD
2 stops14h 42m
Delta
Fri 5/110:20 am
SJD
- ORD
2 stops11h 39m
Delta
Deal found 3/2![Delta logo]()
$456
This Aeromexico deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/196:00 am
MDW
- SJD
1 stop9h 04m
Aeromexico
Wed 4/226:00 am
SJD
- MDW
2 stops14h 28m
Aeromexico
Deal found 3/4![Aeromexico logo]()
$456
This Booking.com deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” 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.
Thu 4/212:20 pm
ORD
- SJD
1 stop26h 05m
Viva
Sun 4/128:15 pm
SJD
- ORD
1 stop26h 30m
Viva
Deal found 3/4![Viva logo]()
$457
This Kiwi.com deal was found by Cheapflights users on 3/3. 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 3/1711:59 pm
ORD
- SJD
2 stops12h 37m
Volaris
Sat 3/2112:11 pm
SJD
- ORD
1 stop8h 18m
Volaris
Deal found 3/3![Volaris logo]()
$458
This Alaska Airlines deal was found by Cheapflights users on 3/2. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/93:52 pm
ORD
- SJD
2 stops24h 45m
Alaska Airlines
Sat 5/1610:41 am
SJD
- ORD
1 stop24h 33m
Alaska Airlines
Deal found 3/2![Alaska Airlines logo]()
$459
This Kiwi.com deal was found by Cheapflights users on 3/3. 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 3/611:58 pm
ORD
- SJD
1 stop16h 22m
Multiple Airlines
Tue 3/105:05 pm
SJD
- ORD
1 stop28h 40m
Multiple Airlines
Deal found 3/3![Multiple Airlines logo]()
$460
This Kiwi.com deal was found by Cheapflights users on 2/28. 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.
Sun 3/112:15 am
ORD
- SJD
1 stop17h 10m
Multiple Airlines
Thu 3/512:11 pm
SJD
- ORD
1 stop9h 18m
Multiple Airlines
Deal found 2/28![Multiple Airlines logo]()
$461
This CheapOair deal was found by Cheapflights users on 3/3. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/78:48 pm
ORD
- SJD
1 stop19h 49m
Alaska Airlines
Wed 5/1311:20 am
SJD
- ORD
1 stop10h 39m
Alaska Airlines
Deal found 3/3![Alaska Airlines logo]()
$462
This Kiwi.com deal was found by Cheapflights users on 3/3. 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.
Mon 4/62:35 am
ORD
- SJD
1 stop10h 57m
Multiple Airlines
Sat 4/117:47 pm
SJD
- ORD
2 stops47h 33m
Multiple Airlines
Deal found 3/3![Multiple Airlines logo]()
$463
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 March 5, 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 March 5, 2026.
This Southwest deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” 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 4/296:10 am
MDW
- SJD
1 stop6h 40m
Southwest
Wed 4/292:20 pm
SJD
- MDW
1 stop12h 40m
Southwest
Deal found 3/4![Southwest logo]()
$476
This Alaska Airlines deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/258:48 pm
ORD
- SJD
1 stop19h 49m
Alaska Airlines
Sat 5/210:41 am
SJD
- ORD
1 stop24h 32m
Alaska Airlines
Deal found 2/28![Alaska Airlines logo]()
$478
This United Airlines deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” 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.
Wed 4/18:40 am
ORD
- SJD
Nonstop4h 45m
United Airlines
Wed 4/811:52 am
SJD
- ORD
Nonstop4h 17m
United Airlines
Deal found 3/4![United Airlines logo]()
$486
This Delta deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” 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 5/233:50 pm
ORD
- SJD
1 stop8h 35m
Delta
Sat 5/306:00 am
SJD
- ORD
2 stops15h 59m
Delta
Deal found 3/4![Delta logo]()
$530
This United Airlines deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” 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.
Tue 4/78:40 am
ORD
- SJD
Nonstop4h 45m
United Airlines
Sat 4/111:17 pm
SJD
- ORD
1 stop7h 41m
United Airlines
Deal found 3/4![United Airlines logo]()
$497
This Alaska Airlines deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/73:52 pm
ORD
- SJD
2 stops21h 37m
Alaska Airlines
Sun 5/1012:54 pm
SJD
- ORD
2 stops22h 19m
Alaska Airlines
Deal found 2/28![Alaska Airlines logo]()
$517
This Southwest deal was found by Cheapflights users on 3/1. 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.
Sat 4/255:00 am
MDW
- SJD
1 stop6h 30m
Southwest
Sat 5/211:35 am
SJD
- MDW
1 stop9h 10m
Southwest
Deal found 3/1![Southwest logo]()
$525
This Delta deal was found by Cheapflights users on 3/1. 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.
Tue 5/59:50 am
ORD
- SJD
2 stops14h 35m
Delta
Sun 5/1010:25 am
SJD
- ORD
2 stops11h 34m
Delta
Deal found 3/1![Delta logo]()
$549
This United Airlines deal was found by Cheapflights users on 3/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/247:00 am
ORD
- SJD
1 stop7h 05m
United Airlines
Mon 4/2711:52 am
SJD
- ORD
Nonstop4h 17m
United Airlines
Deal found 3/3![United Airlines logo]()
$538
This Alaska Airlines deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” 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 5/289:00 am
ORD
- SJD
1 stop9h 36m
Alaska Airlines
Thu 6/410:41 am
SJD
- ORD
1 stop11h 14m
Alaska Airlines
Deal found 3/4![Alaska Airlines logo]()
$540
This Southwest deal was found by Cheapflights users on 3/1. 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.
Fri 3/278:15 am
MDW
- SJD
1 stop7h 20m
Southwest
Tue 3/3110:10 am
SJD
- MDW
Nonstop3h 55m
Southwest
Deal found 3/1![Southwest logo]()
$585
This Delta deal was found by Cheapflights users on 3/1. 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.
Wed 4/226:00 am
MDW
- SJD
1 stop9h 04m
Delta
Sat 4/2512:36 pm
SJD
- MDW
1 stop7h 52m
Delta
Deal found 3/1![Delta logo]()
$598
This Southwest deal was found by Cheapflights users on 2/28. 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.
Sat 4/116:00 am
MDW
- SJD
2 stops9h 00m
Southwest
Wed 4/152:20 pm
SJD
- MDW
2 stops13h 05m
Southwest
Deal found 2/28![Southwest logo]()
$596
This Delta deal was found by Cheapflights users on 3/1. 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.
Fri 3/277:20 am
ORD
- SJD
1 stop8h 35m
Delta
Tue 3/318:35 am
SJD
- ORD
2 stops13h 19m
Delta
Deal found 3/1![Delta logo]()
$605
This Southwest deal was found by Cheapflights users on 3/1. 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.
Fri 3/209:05 am
MDW
- SJD
Nonstop4h 55m
Southwest
Wed 3/2510:35 am
SJD
- MDW
Nonstop3h 55m
Southwest
Deal found 3/1![Southwest logo]()
$639
This Delta deal was found by Cheapflights users on 2/28. 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 4/116:00 am
MDW
- SJD
1 stop9h 14m
Delta
Wed 4/1512:36 pm
SJD
- MDW
1 stop7h 52m
Delta
Deal found 2/28![Delta logo]()
$653
This Southwest deal was found by Cheapflights users on 3/1. 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.
Fri 3/209:05 am
MDW
- SJD
Nonstop4h 55m
Southwest
Mon 3/2311:55 am
SJD
- MDW
Nonstop4h 00m
Southwest
Deal found 3/1![Southwest logo]()
$645
This Delta deal was found by Cheapflights users on 3/2. 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 3/306:00 am
MDW
- SJD
1 stop7h 30m
Delta
Sat 4/48:35 am
SJD
- MDW
2 stops11h 56m
Delta
Deal found 3/2![Delta logo]()
$680
This Delta deal was found by Cheapflights users on 3/1. 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.
Tue 5/56:00 am
MDW
- SJD
1 stop9h 04m
Delta
Sun 5/106:00 am
SJD
- MDW
2 stops13h 09m
Delta
Deal found 3/1![Delta logo]()
$684
Last-minute flights from Chicago to San José del CaboDiscover last-minute flight deals from Chicago to San José del Cabo. Data last updated March 5, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to San José del Cabo. Data last updated March 5, 2026 and is based on user searches.
This Mytrip deal was found by Cheapflights users on 3/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1112:58 am
ORD
- SJD
3 stops18h 09m
Multiple Airlines
Wed 3/184:08 pm
SJD
- ORD
2 stops20h 58m
Multiple Airlines
Deal found 3/3![Multiple Airlines logo]()
$462
This Mytrip deal was found by Cheapflights users on 3/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1112:58 am
ORD
- SJD
2 stops11h 38m
Volaris
Mon 3/1611:59 am
SJD
- ORD
2 stops21h 20m
Volaris
Deal found 3/3![Volaris logo]()
$478
This eDestinos deal was found by Cheapflights users on 3/3. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1212:59 pm
ORD
- SJD
2 stops24h 15m
Multiple Airlines
Sun 3/155:47 pm
SJD
- ORD
2 stops27h 58m
Multiple Airlines
Deal found 3/3![Multiple Airlines logo]()
$481
This Trip.com deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” 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.
Fri 3/1311:59 pm
ORD
- SJD
1 stop13h 31m
Multiple Airlines
Wed 3/188:40 am
SJD
- ORD
1 stop14h 05m
Multiple Airlines
Deal found 3/4![Multiple Airlines logo]()
$463
This Kiwi.com deal was found by Cheapflights users on 3/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/1311:59 pm
ORD
- SJD
2 stops16h 20m
Volaris
Wed 3/184:08 pm
SJD
- ORD
1 stop11h 28m
Volaris
Deal found 3/2![Volaris logo]()
$464
This CheapOair deal was found by Cheapflights users on 2/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/136:05 am
MDW
- SJD
1 stop30h 11m
Frontier
Sat 3/2111:31 am
SJD
- MDW
1 stop8h 38m
Frontier
Deal found 2/28![Frontier logo]()
$486
This Mytrip deal was found by Cheapflights users on 3/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/1411:59 pm
ORD
- SJD
2 stops12h 37m
Multiple Airlines
Mon 3/234:08 pm
SJD
- ORD
3 stops29h 09m
Multiple Airlines
Deal found 3/3![Multiple Airlines logo]()
$477
This Gotogate deal was found by Cheapflights users on 3/3. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/1411:59 pm
ORD
- SJD
1 stop13h 31m
Volaris
Mon 3/234:08 pm
SJD
- ORD
1 stop11h 28m
Volaris
Deal found 3/3![Volaris logo]()
$485
This Mytrip deal was found by Cheapflights users on 3/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/147:54 pm
MDW
- SJD
2 stops17h 20m
Volaris
Wed 3/182:59 pm
SJD
- MDW
2 stops25h 35m
Volaris
Deal found 3/3![Volaris logo]()
$525
This Kiwi.com deal was found by Cheapflights users on 3/3. 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.
Sun 3/1512:59 pm
ORD
- SJD
3 stops21h 26m
Multiple Airlines
Fri 3/203:36 pm
SJD
- ORD
1 stop17h 43m
Multiple Airlines
Deal found 3/3![Multiple Airlines logo]()
$470
This Kiwi.com deal was found by Cheapflights users on 3/1. 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.
Sun 3/157:23 am
ORD
- SJD
1 stop9h 57m
Volaris
Fri 3/203:36 pm
SJD
- ORD
1 stop17h 43m
Volaris
Deal found 3/1![Volaris logo]()
$473
This Kiwi.com deal was found by Cheapflights users on 3/3. 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.
Sun 3/1512:59 pm
ORD
- SJD
3 stops21h 26m
Multiple Airlines
Thu 3/193:36 pm
SJD
- ORD
1 stop30h 09m
Multiple Airlines
Deal found 3/3![Multiple Airlines logo]()
$479
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 March 5, 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 March 5, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/28. 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.
Sun 4/261:40 am
ORD
- SJD
1 stop10h 29m
Volaris
Deal found 2/28![Volaris logo]()
$90
This Kissandfly.com deal was found by Cheapflights users on 3/2. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/197:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Deal found 3/2![Volaris logo]()
$94
This Trip.com deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” 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 4/77:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Deal found 3/4![Volaris logo]()
$97
This Mytrip deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” 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 5/77:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Deal found 3/4![Volaris logo]()
$98
This Mytrip deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” 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.
Tue 5/57:35 am
ORD
- SJD
1 stop10h 20m
Volaris
Deal found 3/4![Volaris logo]()
$99
This Kiwi.com deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” 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 5/57:35 am
ORD
- SJD
2 stops30h 50m
Multiple Airlines
Deal found 3/4![Multiple Airlines logo]()
$100
This Booking.com deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” 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.
Tue 4/2112:20 pm
ORD
- SJD
1 stop26h 05m
Viva
Deal found 3/4![Viva logo]()
$101
This Gotogate deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” 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.
Wed 5/277:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Deal found 3/4![Volaris logo]()
$105
This Kiwi.com deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” 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 5/51:40 am
ORD
- SJD
2 stops12h 45m
Multiple Airlines
Deal found 3/4![Multiple Airlines logo]()
$106
This Trip.com deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” 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.
Mon 4/271:40 am
ORD
- SJD
1 stop16h 24m
Volaris
Deal found 3/4![Volaris logo]()
$107
This Mytrip deal was found by Cheapflights users on 2/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/107:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Deal found 2/28![Volaris logo]()
$110
This Mytrip deal was found by Cheapflights users on 3/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/37:35 am
ORD
- SJD
1 stop13h 29m
Volaris
Deal found 3/2![Volaris logo]()
$112
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 March 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $454 (Cheapflightsfares) |
One-way from | $90 (Kiwi.com) |
Popular in | March |
Cheapest in | September |
Average price | $719 |
Good round-trip deal | $540 or less |
Good one-way deal | $246 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 March 5, 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
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Wed 4/29
6:10 am-10:50 am
1 stop6h 40m
San José del Cabo Los Cabos
Wed 4/29
2:20 pm-5:00 am
1 stop12h 40m
$476
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Sat 4/25
8:48 pm-2:37 pm
1 stop19h 49m
San José del Cabo Los Cabos
Sat 5/2
10:41 am-1:13 pm
1 stop24h 32m
$478
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Wed 4/1
8:40 am-11:25 am
Nonstop4h 45m
San José del Cabo Los Cabos
Wed 4/8
11:52 am-6:09 pm
Nonstop4h 17m
$486
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Tue 4/7
8:40 am-11:25 am
Nonstop4h 45m
San José del Cabo Los Cabos
Sat 4/11
1:17 pm-10:58 pm
1 stop7h 41m
$497
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Thu 5/7
3:52 pm-11:29 am
2 stops21h 37m
San José del Cabo Los Cabos
Sun 5/10
12:54 pm-1:13 pm
2 stops22h 19m
$517
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Sat 4/25
5:00 am-9:30 am
1 stop6h 30m
San José del Cabo Los Cabos
Sat 5/2
11:35 am-10:45 pm
1 stop9h 10m
$525
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Sat 5/23
3:50 pm-10:25 pm
1 stop8h 35m
San José del Cabo Los Cabos
Sat 5/30
6:00 am-11:59 pm
2 stops15h 59m
$530
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Fri 4/24
7:00 am-12:05 pm
1 stop7h 05m
San José del Cabo Los Cabos
Mon 4/27
11:52 am-6:09 pm
Nonstop4h 17m
$538
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Thu 5/28
9:00 am-4:36 pm
1 stop9h 36m
San José del Cabo Los Cabos
Thu 6/4
10:41 am-11:55 pm
1 stop11h 14m
$540
ChicagoSan José del Cabo
ORD - SJD
ORDSJD
Chicago O'Hare Intl
Tue 5/5
9:50 am-10:25 pm
2 stops14h 35m
San José del Cabo Los Cabos
Sun 5/10
10:25 am-11:59 pm
2 stops11h 34m
$549
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 March.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*2 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
How far ahead should I book a flight from Chicago to San José del Cabo?
Use this chart to determine the optimal time to book a round-trip flight from Chicago to San José del Cabo. Price data was last updated on February 27, 2026.
Booking 41 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, March is the cheapest month in which you can book a flight from Chicago to San José del Cabo (average of $263). Flying from Chicago to San José del Cabo in September is currently the most expensive (average of $395). 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 March 5, 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 50% 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.
Guadalajara (GDL) is the most affordable 1-stop option, with an average round-trip price of $344.
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 March 5, 2026.
Peruse reviews from past customers who have flown with Southwest, United Airlines, and American 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
Food
7.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Boarding
8.1
Food
7.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Boarding
8.1
Food
7.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Boarding
8.1
Food
7.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Boarding
8.1
Food
7.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Boarding
8.1
Food
7.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
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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Complete your trip
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Search flights from Chicago to San José del Cabo by cabin class
Find flights from Chicago to San José del Cabo, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and San José del Cabo flights
Browse other Chicago and San José del Cabo flight options. Last updated on March 5, 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 March 5, 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 March 5, 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 March 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$184 | Average$500 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$252 | Average$388 | FlexibilityNo cancel fee | On-time79% | |
| Cheapest$266 | Average$358 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$415 | Average$617 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$416 | Average$607 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$475 | Average$692 | FlexibilityNo cancel fee | On-time63% |