$202 Cheap Flights from San José del Cabo (SJD) to Chicago (ORD)

View $202 flight on Mon, Nov 24, 2025Opens in a new window

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

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

Prices were available within the past 7 days and start at $202 for one-way flights and $365 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Volaris
Sat, Feb 14 - Tue, Feb 17
SJD
San José del Cabo
ORD
Chicago
$365 Roundtrip, found 6 hours ago
$365
Roundtrip
found 6 hours ago
Select Volaris flight, departing Sat, Feb 14 from San José del Cabo to Chicago, returning Tue, Feb 17, priced at $365 found 6 hours ago
Viva
Fri, Dec 12 - Mon, Dec 15
SJD
San José del Cabo
ORD
Chicago
$366 Roundtrip, found 6 days ago
$366
Roundtrip
found 6 days ago
Select Viva flight, departing Fri, Dec 12 from San José del Cabo to Chicago, returning Mon, Dec 15, priced at $366 found 6 days ago
Volaris
Sat, Feb 14 - Sun, Feb 22
SJD
San José del Cabo
ORD
Chicago
$367 Roundtrip, found 1 day ago
$367
Roundtrip
found 1 day ago
Select Volaris flight, departing Sat, Feb 14 from San José del Cabo to Chicago, returning Sun, Feb 22, priced at $367 found 1 day ago
Volaris
Fri, Nov 21 - Mon, Dec 1
SJD
San José del Cabo
ORD
Chicago
$369 Roundtrip, found 1 hour ago
$369
Roundtrip
found 1 hour ago
Select Volaris flight, departing Fri, Nov 21 from San José del Cabo to Chicago, returning Mon, Dec 1, priced at $369 found 1 hour ago
United
Tue, Dec 23 - Wed, Dec 31
SJD
San José del Cabo
ORD
Chicago
$369 Roundtrip, found 6 hours ago
$369
Roundtrip
found 6 hours ago
Select United flight, departing Tue, Dec 23 from San José del Cabo to Chicago, returning Wed, Dec 31, priced at $369 found 6 hours ago
Aeromexico
Wed, Jan 28 - Mon, Feb 2
SJD
San José del Cabo
ORD
Chicago
$370 Roundtrip, just found
$370
Roundtrip
just found
Select Aeromexico flight, departing Wed, Jan 28 from San José del Cabo to Chicago, returning Mon, Feb 2, priced at $370 just found
American Airlines
Wed, Dec 3 - Mon, Dec 8
SJD
San José del Cabo
ORD
Chicago
$370 Roundtrip, just found
$370
Roundtrip
just found
Select American Airlines flight, departing Wed, Dec 3 from San José del Cabo to Chicago, returning Mon, Dec 8, priced at $370 just found
Aeromexico
Mon, Jan 19 - Thu, Jan 22
SJD
San José del Cabo
ORD
Chicago
$370 Roundtrip, found 5 days ago
$370
Roundtrip
found 5 days ago
Select Aeromexico flight, departing Mon, Jan 19 from San José del Cabo to Chicago, returning Thu, Jan 22, priced at $370 found 5 days ago
Volaris
Wed, Oct 22 - Sat, Nov 8
SJD
San José del Cabo
ORD
Chicago
$371 Roundtrip, found 1 day ago
$371
Roundtrip
found 1 day ago
Select Volaris flight, departing Wed, Oct 22 from San José del Cabo to Chicago, returning Sat, Nov 8, priced at $371 found 1 day ago
United
Thu, Nov 13 - Sun, Nov 30
SJD
San José del Cabo
ORD
Chicago
$372 Roundtrip, found 16 hours ago
$372
Roundtrip
found 16 hours ago
Select United flight, departing Thu, Nov 13 from San José del Cabo to Chicago, returning Sun, Nov 30, priced at $372 found 16 hours ago

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

August is typically the cheapest month to fly

From $306 - $547 per traveler.

Alternative airports near Chicago

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

Select flight to Midway Intl. MDW. Closest option available. Average driving time to city center is 16 minutes. Flights from $433
MDW
Midway Intl.
Closest
Average driving time to city center16 min
Flights from $433

Frequently asked questions

How much does a flight from Los Cabos Intl. Airport (SJD) to O'Hare Intl. Airport (ORD) cost?
Lock in a cheap one-way flight from $202 or cheap return flight from $365 from Los Cabos Intl. Airport (SJD) to O'Hare Intl. Airport (ORD) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Los Cabos Intl. Airport (SJD) to O'Hare Intl. Airport (ORD)?
The cheapest month to fly from SJD to ORD is February, when there's less demand. Off-peak season is usually when you'll find cheap fares for travel between these airports.
Which airlines fly direct from Los Cabos Intl. Airport (SJD) to O'Hare Intl. Airport (ORD)?
Catch a direct flight with United Airlines and go straight from Los Cabos Intl. Airport (SJD) to O'Hare Intl. Airport (ORD).
What is the cheapest airline that flies from Los Cabos Intl. Airport (SJD) to O'Hare Intl. Airport (ORD)?
While prices may vary depending on your travel dates, American Airlines and United Airlines are popular choices for flights between Los Cabos Intl. Airport (SJD) and O'Hare Intl. Airport (ORD). You can also compare airlines on Expedia and use the "Sort by" filter to find the cheapest fare for your SJD to ORD flight.
How many flights per day from Los Cabos Intl. Airport (SJD) to O'Hare Intl. Airport (ORD)?
With, on average, 2 direct flights departing from Los Cabos Intl. Airport (SJD) to O'Hare Intl. Airport (ORD) each day, you'll be taking off on vacation soon enough.
What are the most popular departure times for flights from Los Cabos Intl. Airport (SJD) to O'Hare Intl. Airport (ORD)?
Flights between SJD and ORD are their busiest at 12 PM. If you want a more relaxed atmosphere and possibly cheaper fares, choose a time outside the usual busy windows.
What day of the week has the most flights from SJD to ORD?
If you fly on a Saturday, you'll get the widest range of options for flights from Los Cabos Intl. Airport (SJD) to O'Hare Intl. Airport (ORD).
What is the earliest flight from Los Cabos Intl. Airport (SJD) to O'Hare Intl. Airport (ORD)?
The first flight of the day jetting off from Los Cabos Intl. Airport (SJD) is at around 12:49PM UTC-7. Board this plane and you'll touch down at O'Hare Intl. Airport (ORD) at approximately 5:58PM UTC-6. The overall travel time is 4h 9m.
How long does it take to fly from Los Cabos Intl. Airport (SJD) to O'Hare Intl. Airport (ORD)?
Typically, it takes 4 hours and 12 minutes to fly the 1,800 mi from SJD to ORD.
What airline has the least delays from SJD to ORD?
Consider booking with United Airlines if you'd like to fly straight from Los Cabos Intl. Airport (SJD) to O'Hare Intl. Airport (ORD) without any interruptions. This carrier has the strongest track record for punctuality, with an on-time score of 91%. Want to be updated if anything changes? You can keep an eye on your flight status using the Expedia App.
What is the best time to fly from Los Cabos Intl. Airport (SJD) to O'Hare Intl. Airport (ORD)?
To avoid potential delays on the Los Cabos Intl. Airport (SJD) to O'Hare Intl. Airport (ORD) route, aim to travel before 3 PM. Flights after this time are 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 Chicago from Los Cabos Intl. Airport (SJD)?
Explore your flight options from Los Cabos Intl. Airport (SJD) to O'Hare Intl. Airport (ORD). This is the only Chicago airport you can fly into if you're taking a direct flight.
Is it cheaper to buy a plane ticket from Los Cabos Intl. Airport (SJD) to O'Hare Intl. Airport (ORD) last-minute?
Booking your ticket from SJD to ORD shortly before your getaway is usually more expensive. But if there's some wiggle room with your travel times and dates, you could score a cheap last-minute fare.
Is it cheaper to book a SJD to ORD flight and hotel package?
You'll generally save money by securing a SJD to ORD flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's easy to manage it all in one place. After selecting your preferred flights and accommodations, you can add extras like activities, tours and car rentals.
Can I cancel or change the date of my flight from Los Cabos Intl. Airport (SJD) to O'Hare Intl. Airport (ORD)?
If you booked your SJD to ORD flight in the last 24 hours, you may be able to cancel or modify it without any fees. Depending on the airline and the ticket type you purchased, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal for further details.

Travel information

Travel information

Origin airport
Los Cabos Intl.
Destination airport
O'Hare Intl.
Airlines serving
Aeromexico, Air Canada, Alaska Airlines, American Airlines, Delta, Frontier Airlines, Hawaiian Airlines, Southwest Airlines, United, Viva, Volaris
Roundtrip price
$365
Distance
1806 mi
Average flight time
6 hours 19 mins

Book with confidence

Book with confidence

San José del Cabo to Chicago Flights

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

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 San José del Cabo to Chicago are during the month of February. You can find some of the cheapest flights from San José del Cabo to Chicago with Expedia's search tool and vast selection of airlines.

 

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

Sunday is one of the best days to book for cheap flights from San José del Cabo to Chicago: 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 San José del Cabo to Chicago

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 San José del Cabo to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $202 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 San José del Cabo to Chicago 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 San José del Cabo to Chicago 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.

 

San José del Cabo to Chicago Flights

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*Available to One Key members.