S$226 Cheap Flights from Chicago to San José del Cabo

View S$226 flight on Sun, 21 Sep, 2025Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Los Cabos Intl. Airport (SJD)

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Cheap Flights from Chicago to San José del Cabo (ORD-SJD)

Prices were available within the past 7 days and start at S$226 for one-way flights and S$565 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Tue, 25 Nov - Wed, 3 Dec
ORD
Chicago
SJD
San José del Cabo
S$565 Return, found 4 days ago
S$565
Return
found 4 days ago
Select American Airlines flight, departing Tue, 25 Nov from Chicago to San José del Cabo, returning Wed, 3 Dec, priced at S$565 found 4 days ago
American Airlines
Tue, 25 Nov - Wed, 3 Dec
ORD
Chicago
SJD
San José del Cabo
S$572 Return, found 4 days ago
S$572
Return
found 4 days ago
Select American Airlines flight, departing Tue, 25 Nov from Chicago to San José del Cabo, returning Wed, 3 Dec, priced at S$572 found 4 days ago
Air Canada
Sun, 23 Nov - Wed, 3 Dec
ORD
Chicago
SJD
San José del Cabo
S$590 Return, found 4 days ago
S$590
Return
found 4 days ago
Select Air Canada flight, departing Sun, 23 Nov from Chicago to San José del Cabo, returning Wed, 3 Dec, priced at S$590 found 4 days ago
Air Canada
Sun, 23 Nov - Wed, 3 Dec
ORD
Chicago
SJD
San José del Cabo
S$597 Return, found 4 days ago
S$597
Return
found 4 days ago
Select Air Canada flight, departing Sun, 23 Nov from Chicago to San José del Cabo, returning Wed, 3 Dec, priced at S$597 found 4 days ago
United
Tue, 25 Nov - Wed, 3 Dec
ORD
Chicago
SJD
San José del Cabo
S$597 Return, found 4 days ago
S$597
Return
found 4 days ago
Select United flight, departing Tue, 25 Nov from Chicago to San José del Cabo, returning Wed, 3 Dec, priced at S$597 found 4 days ago
American Airlines
Tue, 25 Nov - Wed, 3 Dec
ORD
Chicago
SJD
San José del Cabo
S$599 Return, found 4 days ago
S$599
Return
found 4 days ago
Select American Airlines flight, departing Tue, 25 Nov from Chicago to San José del Cabo, returning Wed, 3 Dec, priced at S$599 found 4 days ago
American Airlines
Tue, 25 Nov - Tue, 2 Dec
ORD
Chicago
SJD
San José del Cabo
S$606 Return, found 4 days ago
S$606
Return
found 4 days ago
Select American Airlines flight, departing Tue, 25 Nov from Chicago to San José del Cabo, returning Tue, 2 Dec, priced at S$606 found 4 days ago
United
Sun, 23 Nov - Wed, 3 Dec
ORD
Chicago
SJD
San José del Cabo
S$621 Return, found 4 days ago
S$621
Return
found 4 days ago
Select United flight, departing Sun, 23 Nov from Chicago to San José del Cabo, returning Wed, 3 Dec, priced at S$621 found 4 days ago
Delta
Sun, 21 Sep - Mon, 20 Oct
ORD
Chicago
SJD
San José del Cabo
S$649 Return, found 5 hours ago
S$649
Return
found 5 hours ago
Select Delta flight, departing Sun, 21 Sep from Chicago to San José del Cabo, returning Mon, 20 Oct, priced at S$649 found 5 hours ago
Aeromexico
Sat, 24 Jan - Thu, 29 Jan
ORD
Chicago
SJD
San José del Cabo
S$934 Return, found 17 hours ago
S$934
Return
found 17 hours ago
Select Aeromexico flight, departing Sat, 24 Jan from Chicago to San José del Cabo, returning Thu, 29 Jan, priced at S$934 found 17 hours ago

Find the cheapest month to fly from Chicago (ORD) to San José del Cabo (SJD)

March is typically the cheapest month to fly

From S$404 - S$551 per traveller.

Graph displaying average flight prices per month

Chicago to San José del Cabo route information
Origin airport
O'Hare Intl.
Destination airport
Los Cabos Intl.
Airlines serving
Aeromexico, Air Canada, American Airlines, Delta, United
Return price
S$564
Distance
2890 km

Perfect flights from Chicago to San José del Cabo

Your Journey from Chicago to San José del Cabo

Start your unforgettable journey with Expedia. Our broad selection of flights from Chicago to San José del Cabo caters to every travel need. Whether you're yearning for a romantic escape, a solo adventure, or a cultural immersion, we've got you covered.
 

Choosing Your Ideal Flight

With Expedia, you have access to a wide range of airlines, including Delta, American Airlines, United, Air Canada, Aeromexico. Our selection of flights from O'Hare Intl. to Los Cabos Intl. caters to every traveler's requirements, ensuring your journey aligns with your schedule. With options from 20 airlines, you're bound to find the perfect flight.
 

Maximizing Value with Chicago to San José del Cabo Flights

Experience the joy of finding cheap flights from O'Hare Intl. to Los Cabos Intl. that fit your budget. Keep an eye out for our special deals and discounts, and check our flexible one-way fares from S$226 and roundtrip prices from S$565*.
 

Pre-Flight Essentials

Ensure a smooth journey from Chicago to San José del Cabo with Expedia. From information about check-in times and in-flight amenities to guidance on baggage policies, we provide all the essentials to prepare you for your flight.
 

Experience the Vibrant San José del Cabo

Picture yourself stepping off the plane in San José del Cabo and immersing yourself in the unique atmosphere of . From local markets to cultural festivals, each city offers its distinct charm. Make the most of your trip by exploring local attractions and indulging in the local cuisine. With Expedia, explore all this and more, tailored to your budget.
 

Added Convenience on Your Chicago to San José del Cabo Flight

Traveling with Expedia is more than just a flight. We offer details about in-flight amenities, baggage policies, and more to ensure a smooth and hassle-free journey. Choose from our variety of airlines and embark on a memorable journey from Chicago to San José del Cabo.
 

Beyond the Flight – Exploring San José del Cabo

With Expedia, your adventure extends beyond the flight. Explore San José del Cabo at your own pace by renting a car or booking a hotel. Discover hidden gems off the beaten path and create unforgettable memories.
 

Book Your Flight from Chicago to San José del Cabo with Confidence

Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support make your travel experience seamless and stress-free. Embark on your journey from Chicago to San José del Cabo with confidence. Book your travel arrangements with Expedia today.
 
*Note: Prices may vary based on availability and are subject to change.

Frequently asked questions

How much is a flight from O'Hare Airport to SJD?
The lowest price advertised for a round-trip flight from O'Hare Airport to Los Cabos Airport is S$565. But you better act fast. This price is based on fares available within the last 7 days on Expedia for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from O'Hare Airport to Los Cabos Airport?
The majority of flights can be conveniently cancelled online, but whether or not you incur a fee varies between airlines. If you do have to cancel your getaway, follow the instructions in the Customer Service Portal.
How do I find cheap flights from ORD to SJD that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for ORD to SJD flights, you'll see a "no change fees" filter for you to select.
How far is the flight from ORD to Los Cabos Airport?
Around 2,900 kilometres separates Chicago and San Jose del Cabo, so pack something to help you while away a couple of hours. That novel you haven't finished will be perfect.
Which airlines fly direct from O'Hare Intl. Airport (ORD) to Los Cabos Intl. Airport (SJD)?
With 34 flights every month operating from O'Hare Airport to SJD, United Airlines (UA) is a top choice. Operating 21 flights a month along this route, American Airlines (AA) is another good choice.
Are O'Hare Airport to SJD flight tickets cheaper when they're purchased at the last minute?
It is possible to nab an awesome last-minute deal from ORD to Los Cabos Airport, but it can also be hit-or-miss. As many airlines advertise prices up to a year in advance, it's worthwhile keeping an eye on fares early and being ready to pounce when you see a bargain. Expedia compares carrier prices and updates flight deals often, so you can rest assured you're always seeing the latest offers.

Explore a world of travel with Expedia

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