$156 Cheap flight deals from Chicago (CHI) to San José del Cabo (SJD)

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This Weekend's Flight Deals from Chicago to San José del Cabo

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Sep 27 - Thu, Oct 2
ORD
O'Hare Intl.
SJD
Los Cabos Intl.
$413 Roundtrip, found 4 hours ago
$413
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Sat, Sep 27 from O'Hare Intl. to Los Cabos Intl., returning Thu, Oct 2, priced at $413 found 4 hours ago
Sun, Sep 28 - Sat, Oct 4
MDW
Midway Intl.
SJD
Los Cabos Intl.
$418 Roundtrip, found 3 days ago
$418
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Sun, Sep 28 from Midway Intl. to Los Cabos Intl., returning Sat, Oct 4, priced at $418 found 3 days ago

Airfares from $156 One Way, $359 Round Trip from Chicago to San José del Cabo

Prices starting at $359 for return flights and $156 for one-way flights to San José del Cabo were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Tue, Nov 11 - Sat, Nov 15
ORD
Chicago
SJD
San José del Cabo
$359 Roundtrip, found 22 hours ago
$359
Roundtrip
found 22 hours ago
Select Volaris flight, departing Tue, Nov 11 from Chicago to San José del Cabo, returning Sat, Nov 15, priced at $359 found 22 hours ago
Sun, Oct 19 - Tue, Oct 21
ORD
Chicago
SJD
San José del Cabo
$363 Roundtrip, found 1 day ago
$363
Roundtrip
found 1 day ago
Select Delta flight, departing Sun, Oct 19 from Chicago to San José del Cabo, returning Tue, Oct 21, priced at $363 found 1 day ago
Sun, Oct 19 - Wed, Oct 22
ORD
Chicago
SJD
San José del Cabo
$363 Roundtrip, found 1 hour ago
$363
Roundtrip
found 1 hour ago
Select Aeromexico flight, departing Sun, Oct 19 from Chicago to San José del Cabo, returning Wed, Oct 22, priced at $363 found 1 hour ago
Sat, Oct 18 - Tue, Oct 21
ORD
Chicago
SJD
San José del Cabo
$363 Roundtrip, just found
$363
Roundtrip
just found
Select American Airlines flight, departing Sat, Oct 18 from Chicago to San José del Cabo, returning Tue, Oct 21, priced at $363 just found
Sun, Oct 19 - Wed, Oct 22
MDW
Chicago
SJD
San José del Cabo
$373 Roundtrip, found 1 hour ago
$373
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Sun, Oct 19 from Chicago to San José del Cabo, returning Wed, Oct 22, priced at $373 found 1 hour ago

San José del Cabo economy flight packages

Price found within the past 48 hours. Click for updated prices.
The Towers at Pueblo Bonito Pacifica - All Inclusive
4.5-star property

The Towers at Pueblo Bonito Pacifica - All Inclusive

9/10 Wonderful! (70 reviews)

Oct 24 - Oct 28

4 night stay

Chicago (CHI) to San José del Cabo (SJD)

Alaska Airlines • Non-stop • Coach

San José del Cabo (SJD) to Chicago (CHI)

United • Non-stop • Coach
Price was $2,953, price is now $1,510 per person
$1,510
per person
found 1 day ago
An incredible all inclusive adults only resort. Our butler was helpful and the entire staff was friendly. Beautiful property and great amenities

Reviewed on Oct 10, 2020

Hotel Riu Palace Baja California - Adults Only - All Inclusive
4.5-star property

Hotel Riu Palace Baja California - Adults Only - All Inclusive

8.8/10 Excellent! (4,282 reviews)

Oct 28 - Nov 4

7 night stay

Chicago (CHI) to San José del Cabo (SJD)

United • Non-stop roundtrip • Coach
Price was $2,990, price is now $1,533 per person
$1,533
per person
found 1 day ago
This place was perfect for a vacation. I liked the activities they had at the pool during the day. The staff was so nice and helpful. The only thing I did not like was that Uber could not pick you up at the entrance of the hotel and you had to walk all the way down the driveway exit to get picked up.

Reviewed on Sep 6, 2025

Quivira Los Cabos Condos & Homes - Vacation Rentals
4.0-star property

Quivira Los Cabos Condos & Homes - Vacation Rentals

8.2/10 Very Good! (39 reviews)

Nov 6 - Nov 11

5 night stay

Chicago (CHI) to San José del Cabo (SJD)

Volaris • Non-stop • Coach

San José del Cabo (SJD) to Chicago (CHI)

American Airlines • Non-stop • Coach
Save 100% on your flight
Price was $3,269, price is now $1,734 per person
$1,734
per person
found 11 hours ago
It was beyond our expectations everything was perfect. Beautiful property, great kind and helpful staff.

Reviewed on Jul 23, 2019

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San José del Cabo packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
Vista Encantada Spa Resort & Residences
4.5-star property

Vista Encantada Spa Resort & Residences

8.8/10 Excellent! (32 reviews)

Nov 11 - Nov 16

5 night stay

Chicago (CHI) to San José del Cabo (SJD)

Aeromexico • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $3,636, price is now $2,063 per person
$2,063
per person
found 1 day ago
We stayed there for 5 days 4 nights over thanksgiving, it was a wonderful stay. The hotel has beautiful view of the hills and ocean! The rooftop pool is amazing! The staff was friendly and very helpful especially our personal butler Omar! Definitely recommend this hotel to my friends!

Reviewed on Nov 30, 2020

Grand Fiesta Americana Los Cabos All Inclusive Golf & Spa
4.5-star property

Grand Fiesta Americana Los Cabos All Inclusive Golf & Spa

8.8/10 Excellent! (1,016 reviews)

Nov 11 - Nov 16

5 night stay

Chicago (CHI) to San José del Cabo (SJD)

Aeromexico • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $4,474, price is now $2,503 per person
$2,503
per person
found 1 day ago
This was our second time staying at this resort, and it was just as good as the first. The food and service at every single restaurant is always fantastic. I can't even pick a favorite because they are all different and equally good. The rooms have comfortable beds and are kept very clean and stocked with snacks and drinks. Deep tissue massages and facials with Amparo and Consuelo at the Somma Wine Spa were relaxing and rejuvenating. Byan at the pool and beach area went out of his way to give us excellent service every day. Our kids loved ice cream in the lobby and snorkeling every day to see all the amazingly colored fish right as you step in to the ocean - 10/10 wonderful resort.

Reviewed on Aug 17, 2025

Pueblo Bonito Montecristo Luxury Villas - All Inclusive
4.5-star property

Pueblo Bonito Montecristo Luxury Villas - All Inclusive

8.8/10 Excellent! (231 reviews)

Nov 11 - Nov 16

5 night stay

Chicago (CHI) to San José del Cabo (SJD)

Aeromexico • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $4,589, price is now $2,602 per person
$2,602
per person
found 1 day ago
I recently had the pleasure of staying at the Montecristo Villas at Pueblo Bonito, and I can confidently say it was one of the most luxurious and memorable experiences I’ve ever had. From the moment we arrived, we were treated like royalty. The check-in process was smooth and efficient, with friendly staff who made us feel right at home. Our villa was absolutely stunning. It featured spacious, elegantly decorated rooms with all the modern amenities you could ask for. The private infinity pool was a highlight, offering breathtaking views of the Pacific Ocean that made every sunrise and sunset a magical experience. The outdoor terrace with a hot tub and barbecue area was perfect for relaxing evenings. The resort itself has everything you could possibly need. We enjoyed delicious meals at the on-site restaurants, which offered a wide variety of cuisine, all of which was top-notch. The concierge service was incredibly helpful, arranging activities and excursions that made our stay even more special. Whether we wanted to explore the local culture, indulge in some shopping, or just relax on the pristine beaches, everything was easily accessible. One of the standout aspects of our stay was the impeccable service. Every staff member we encountered went above and beyond to ensure our comfort and satisfaction. From the housekeeping team who kept our villa spotless to the attentive poolside servers, the level of hospitality was truly exceptional. Montecristo Villas at Pueblo Bonito

Reviewed on May 18, 2024

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San José del Cabo first class flight packages

Price found within the past 48 hours. Click for updated prices.
Grand Velas Boutique Hotel - Adults Only - All Inclusive
5.0-star property

Grand Velas Boutique Hotel - Adults Only - All Inclusive

10/10 Exceptional! (55 reviews)

Nov 5 - Nov 9

4 night stay

Chicago (ORD) to San José del Cabo (SJD)

United • Roundtrip • FirstClass
Price was $9,392, price is now $7,033 per person
$7,033
per person
found 5 hours ago
Las Ventanas al Paraiso, A Rosewood Resort
5.0-star property

Las Ventanas al Paraiso, A Rosewood Resort

9.8/10 Exceptional! (379 reviews)

Nov 5 - Nov 9

4 night stay

Chicago (ORD) to San José del Cabo (SJD)

United • Roundtrip • FirstClass
Price was $9,868, price is now $7,790 per person
$7,790
per person
found 5 hours ago
amazing property will be back

Reviewed on Mar 4, 2025

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More About Flying To San José del Cabo from Chicago

Route Information for Flights from Chicago to San José del Cabo

Origin Airport IATA Code
CHI
Destination Airport IATA Code
SJD
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to San José del Cabo

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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.