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

View $160 flight on Tue, Apr 28, 2026Opens in a new window

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

Today's featured flight deals from Chicago O'Hare Intl. Airport (ORD) to Los Cabos Intl. Airport (SJD)

Nonstop
Carry-on included
Lower price than typical

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 $363 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Wed, Dec 10 - Wed, Dec 17
ORD
Chicago
SJD
San José del Cabo
$363 Roundtrip, just found
$363
Roundtrip
just found
Select American Airlines flight, departing Wed, Dec 10 from Chicago to San José del Cabo, returning Wed, Dec 17, priced at $363 just found
United
Wed, Dec 10 - Wed, Dec 17
ORD
Chicago
SJD
San José del Cabo
$363 Roundtrip, just found
$363
Roundtrip
just found
Select United flight, departing Wed, Dec 10 from Chicago to San José del Cabo, returning Wed, Dec 17, priced at $363 just found
United
Sat, Nov 15 - Sat, Nov 22
ORD
Chicago
SJD
San José del Cabo
$364 Roundtrip, found 1 hour ago
$364
Roundtrip
found 1 hour ago
Select United flight, departing Sat, Nov 15 from Chicago to San José del Cabo, returning Sat, Nov 22, priced at $364 found 1 hour ago
American Airlines
Tue, Nov 11 - Thu, Nov 13
ORD
Chicago
SJD
San José del Cabo
$365 Roundtrip, found 15 hours ago
$365
Roundtrip
found 15 hours ago
Select American Airlines flight, departing Tue, Nov 11 from Chicago to San José del Cabo, returning Thu, Nov 13, priced at $365 found 15 hours ago
United
Tue, Dec 2 - Thu, Dec 11
ORD
Chicago
SJD
San José del Cabo
$366 Roundtrip, found 5 hours ago
$366
Roundtrip
found 5 hours ago
Select United flight, departing Tue, Dec 2 from Chicago to San José del Cabo, returning Thu, Dec 11, priced at $366 found 5 hours ago
Alaska Airlines
Mon, Nov 17 - Tue, Nov 18
ORD
Chicago
SJD
San José del Cabo
$367 Roundtrip, found 10 hours ago
$367
Roundtrip
found 10 hours ago
Select Alaska Airlines flight, departing Mon, Nov 17 from Chicago to San José del Cabo, returning Tue, Nov 18, priced at $367 found 10 hours ago
Delta
Thu, Dec 4 - Tue, Dec 9
ORD
Chicago
SJD
San José del Cabo
$368 Roundtrip, just found
$368
Roundtrip
just found
Select Delta flight, departing Thu, Dec 4 from Chicago to San José del Cabo, returning Tue, Dec 9, priced at $368 just found
American Airlines
Mon, Dec 15 - Sun, Dec 21
ORD
Chicago
SJD
San José del Cabo
$368 Roundtrip, found 3 hours ago
$368
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Mon, Dec 15 from Chicago to San José del Cabo, returning Sun, Dec 21, priced at $368 found 3 hours ago
Volaris
Tue, Apr 28 - Tue, May 5
ORD
Chicago
SJD
San José del Cabo
$369 Roundtrip, just found
$369
Roundtrip
just found
Select Volaris flight, departing Tue, Apr 28 from Chicago to San José del Cabo, returning Tue, May 5, priced at $369 just found
United
Sun, Dec 14 - Wed, Dec 24
ORD
Chicago
SJD
San José del Cabo
$370 Roundtrip, found 3 hours ago
$370
Roundtrip
found 3 hours ago
Select United flight, departing Sun, Dec 14 from Chicago to San José del Cabo, returning Wed, Dec 24, priced at $370 found 3 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 $324 - $429 per traveler.

Alternative airports near San José del Cabo

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Los Cabos Intl. SJD. Cheapest and Closest option available. Average driving time to city center is 16 minutes. Flights from $524
SJD
Los Cabos Intl.
CheapestClosest
Average driving time to city center16 min
Flights from $524

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Los Cabos Intl. Airport (SJD) cost?
Get a cheap one-way flight from $160 or cheap return flight from $363 from O'Hare Intl. Airport (ORD) to Los Cabos Intl. Airport (SJD) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from O'Hare Intl. Airport (ORD) to Los Cabos Intl. Airport (SJD)?
December is the cheapest month to fly from ORD to SJD. Traveling during quieter months is often the key to better flight prices.
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 O'Hare Intl. Airport (ORD) to Los Cabos Intl. Airport (SJD)?
While prices can vary depending on when you travel, United Airlines and American Airlines are often among the top picks for flights between O'Hare Intl. Airport (ORD) and Los Cabos Intl. Airport (SJD). You can also compare airlines on Expedia and use the "Sort by" filter to find the lowest fare for your ORD to SJD flight.
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.

Travel information

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, Volaris
Roundtrip price
$363
Distance
1806 mi
Average flight time
3 hours 10 mins

Book with confidence

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 December. 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.

 

Chicago to San José del Cabo Flights

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*Available to One Key members.