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

View AU$642 flight on Thu, 18 Dec. 2025Opens in a new window

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

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

Prices were available within the past 7 days for one-way flights and round trip tickets for the period specified. Prices and availability are subject to change. Additional terms apply.

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

August is typically the cheapest month to fly

From AU$509 - AU$1,130 per traveller.

Graph displaying average flight prices per month

Flight from Chicago to San José del Cabo route information
Origin airport
O'Hare Intl.
Destination airport
Los Cabos Intl.
Distance
2890 km
Average flight time
3 hours 40 mins

Your quick guide to flights from Chicago to San José del Cabo

Pick up great flights from Chicago to San José del Cabo

With Expedia, you have your pick of flights a day with 18 airlines covering flights from Chicago to San José del Cabo. Whether you’re on a business trip, a family holiday or a luxury break, just enter your travel dates, hit search then check out your choice of flights. Select from return, one way or multi-city flights, and use the advance search tool if you want a direct or refundable flight. You can narrow your search to show you just your preferred cabin class and airline, too. It’s all easy. You can book direct flights from Chicago to San José del Cabo that take around hours.

Find cheap flights from Chicago to San José del Cabo

From the great flight deals with prices currently ranging from to , you can choose to see the cheapest flights first. Generally, you can book the cheapest flights from Chicago to San José del Cabo around 4 to 6 weeks in advance. If your travel dates are flexible, try to avoid weekends and peak seasons – when you are more likely to grab the lowest prices. Even last minute, there are some impressive deals. The cheapest time to fly to San José del Cabo is normally in .

Reasons to book your flight from Chicago to San José del Cabo with Expedia

Expedia makes it easy to find, book, and travel, with everything you need all in one place. When you enter your travel details, find fantastic deals just for you on flight tickets from Chicago to San José del Cabo across all the main airline carriers, so you can save time, dollars, and hassle finding the perfect flight. If you think your plans could change, choose refundable flights so any changes won’t cost you more. Book your flight to San José del Cabo right now and, if you join Expedia Rewards, you earn points this time and every time you travel with Expedia.

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 . 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.

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