$160 Cheap Flights from Chicago (ORD) to San José del Cabo (SJD)

View $160 flight on Mon, May 12, 2025Opens in a new window

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

Find available prices by choosing your travel dates.

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

Prices were available within the past 7 days and start at $160 for one-way flights and $360 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Viva Aerobus
Fri, May 16 - Fri, May 23
ORD
Chicago
SJD
San José del Cabo
$360 Roundtrip, found 8 hours ago
$360
Roundtrip
found 8 hours ago
Select Viva Aerobus flight, departing Fri, May 16 from Chicago to San José del Cabo, returning Fri, May 23, priced at $360 found 8 hours ago
Viva Aerobus
Sat, May 10 - Tue, May 13
ORD
Chicago
SJD
San José del Cabo
$361 Roundtrip, found 2 hours ago
$361
Roundtrip
found 2 hours ago
Select Viva Aerobus flight, departing Sat, May 10 from Chicago to San José del Cabo, returning Tue, May 13, priced at $361 found 2 hours ago
Viva Aerobus
Sat, May 10 - Tue, May 13
ORD
Chicago
SJD
San José del Cabo
$363 Roundtrip, found 2 hours ago
$363
Roundtrip
found 2 hours ago
Select Viva Aerobus flight, departing Sat, May 10 from Chicago to San José del Cabo, returning Tue, May 13, priced at $363 found 2 hours ago
Viva Aerobus
Mon, May 12 - Thu, May 22
ORD
Chicago
SJD
San José del Cabo
$365 Roundtrip, found 1 hour ago
$365
Roundtrip
found 1 hour ago
Select Viva Aerobus flight, departing Mon, May 12 from Chicago to San José del Cabo, returning Thu, May 22, priced at $365 found 1 hour ago
Aeromexico
Tue, Aug 19 - Fri, Aug 22
ORD
Chicago
SJD
San José del Cabo
$370 Roundtrip, found 1 hour ago
$370
Roundtrip
found 1 hour ago
Select Aeromexico flight, departing Tue, Aug 19 from Chicago to San José del Cabo, returning Fri, Aug 22, priced at $370 found 1 hour ago
Viva Aerobus
Mon, May 12 - Tue, May 20
ORD
Chicago
SJD
San José del Cabo
$371 Roundtrip, found 6 hours ago
$371
Roundtrip
found 6 hours ago
Select Viva Aerobus flight, departing Mon, May 12 from Chicago to San José del Cabo, returning Tue, May 20, priced at $371 found 6 hours ago
Viva Aerobus
Fri, May 16 - Wed, May 21
ORD
Chicago
SJD
San José del Cabo
$373 Roundtrip, just found
$373
Roundtrip
just found
Select Viva Aerobus flight, departing Fri, May 16 from Chicago to San José del Cabo, returning Wed, May 21, priced at $373 just found
United
Mon, Aug 18 - Thu, Aug 21
ORD
Chicago
SJD
San José del Cabo
$379 Roundtrip, found 6 hours ago
$379
Roundtrip
found 6 hours ago
Select United flight, departing Mon, Aug 18 from Chicago to San José del Cabo, returning Thu, Aug 21, priced at $379 found 6 hours ago
Delta
Wed, Aug 20 - Sat, Aug 23
ORD
Chicago
SJD
San José del Cabo
$384 Roundtrip, found 5 hours ago
$384
Roundtrip
found 5 hours ago
Select Delta flight, departing Wed, Aug 20 from Chicago to San José del Cabo, returning Sat, Aug 23, priced at $384 found 5 hours ago
American Airlines
Tue, Aug 19 - Fri, Aug 22
ORD
Chicago
SJD
San José del Cabo
$402 Roundtrip, found 1 hour ago
$402
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Tue, Aug 19 from Chicago to San José del Cabo, returning Fri, Aug 22, priced at $402 found 1 hour ago
Flights from Chicago (ORD) to San José del Cabo (SJD)
Origin airport
O'Hare Intl.
Destination airport
Los Cabos Intl.
Airlines serving
Aeromexico, Air Canada, Alaska Airlines, American Airlines, Delta, Frontier Airlines, Hawaiian Airlines, JetBlue Airways, Southwest Airlines, United, Viva Aerobus, Volaris
Roundtrip price
$359
Distance
1806 mi

Chicago to San José del Cabo Flights

The cheapest times to fly from Chicago to San José del Cabo

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to San José del Cabo are during the month of May. You can find some of the cheapest flights from Chicago to San José del Cabo with Expedia's search tool and vast selection of airlines.

The best time to book a flight from Chicago to San José del Cabo

Sunday is one of the best days to book for cheap flights from Chicago to San José del Cabo: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

How to find cheap round-trip tickets from Chicago to San José del Cabo

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to San José del Cabo in 2025. You can also book with separate airlines for your outbound and return journeys, from $160 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to San José del Cabo flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to San José del Cabo airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

*Terms apply.

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Los Cabos Intl. Airport (SJD) cost?
You can book cheap return fares starting at $471 from O’Hare Intl. Airport (ORD) to Los Cabos Intl. Airport (SJD). This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a American Airlines flight leaving ORD on May 11 2025 and touching down at SJD. The price was last updated on April 20 2025 and has not changed since.
What is the cheapest month to fly from ORD to SJD?
The cheapest flights from ORD to SJD are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from O'Hare Intl. Airport (ORD) to Los Cabos Intl. Airport (SJD)?
You can fly straight from O’Hare Intl. Airport (ORD) to Los Cabos Intl. Airport (SJD) on a United Airlines flight.
What is the cheapest airline that flies from ORD to SJD?
At the moment, the cheapest carrier offering one-way flights from ORD to SJD is American Airlines. You can jet off on this route from $216. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from ORD on May 11 2025. Prices were last updated on April 20 2025 and have not changed since.
How many flights per day from O'Hare Intl. Airport (ORD) to Los Cabos Intl. Airport (SJD)?
When taking off from O’Hare Intl. Airport (ORD), you can choose from an average of 2 daily direct flights to Los Cabos Intl. Airport (SJD).
What are the most popular departure times for flights from O'Hare Intl. Airport (ORD) to Los Cabos Intl. Airport (SJD)?
Flights between ORD and SJD are their busiest at 9 AM. If you’re after a less crowded experience and possibly cheaper prices, look for a time when demand is lower.
What day of the week has the most flights from ORD to SJD?
If you depart on a Saturday, you’ll get the largest range of options for flights from O’Hare Intl. Airport (ORD) to Los Cabos Intl. Airport (SJD).
What is the earliest flight from O'Hare Intl. Airport (ORD) to Los Cabos Intl. Airport (SJD)?
Take the earliest flight at around 8:20AM UTC-6, heading out of O’Hare Intl. Airport (ORD). You’ll be flying for around 4h 50m, arriving at Los Cabos Intl. Airport (SJD) at approximately 12:10PM UTC-7.
How long does it take to fly from O'Hare Intl. Airport (ORD) to Los Cabos Intl. Airport (SJD)?
Flights from ORD to SJD have an average travel time of 4 hours and 52 minutes. The distance between these two airports is 1,800 mi.
What airline has the least delays from ORD to SJD?
With 87% of flights usually arriving on time, American Airlines has the best on-time performance for direct flights from O’Hare Intl. Airport (ORD) to Los Cabos Intl. Airport (SJD). To keep track of your flight status and receive notifications about any changes, simply head to the Expedia App.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Los Cabos Intl. Airport (SJD)?
Book a flight from O’Hare Intl. Airport (ORD) to Los Cabos Intl. Airport (SJD) that leaves before 3 PM to reduce the likelihood of delays and cancellations. Departures after this time are on average 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG’s global flight data platform.
What airports do you fly into for Cabo San Lucas from O'Hare Intl. Airport (ORD)?
If you’re traveling on a direct flight from O’Hare Intl. Airport (ORD) to Cabo San Lucas, Los Cabos Intl. Airport (SJD) is the only airport you can touch down at.
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Los Cabos Intl. Airport (SJD) last-minute?
Holding off until right before your break to book your flight from ORD to SJD generally means paying more. Although you may find some last-minute deals, they aren’t always guaranteed. Keep your travel schedule open to maximize your chances of landing a bargain.
Is it cheaper to book an ORD to SJD flight and hotel package?
Opting for an ORD to SJD flight and hotel package is typically cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels in one place. Choose from our impressive range of hotels and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Los Cabos Intl. Airport (SJD)?
If you reserved your ORD to SJD flight within the last 24 hours, you may be able to cancel or modify it at no cost. Depending on the airline and the fare type you purchased, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal for further details.

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*Available to One Key members.