$196 Cheap Flights from San José del Cabo (SJD) to Chicago (ORD)

View $196 flight on Tue, Feb 24, 2026Opens in a new window

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

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

Prices were available within the past 7 days and start at $196 for one-way flights and $346 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Sat, Jul 12 - Wed, Jul 16
SJD
San José del Cabo
ORD
Chicago
$346 Roundtrip, found 5 days ago
$346
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, Jul 12 from San José del Cabo to Chicago, returning Wed, Jul 16, priced at $346 found 5 days ago
Volaris
Sun, Mar 15 - Thu, Mar 19
SJD
San José del Cabo
ORD
Chicago
$362 Roundtrip, found 4 days ago
$362
Roundtrip
found 4 days ago
Select Volaris flight, departing Sun, Mar 15 from San José del Cabo to Chicago, returning Thu, Mar 19, priced at $362 found 4 days ago
Volaris
Sat, Feb 7 - Sun, Feb 22
SJD
San José del Cabo
ORD
Chicago
$371 Roundtrip, found 2 days ago
$371
Roundtrip
found 2 days ago
Select Volaris flight, departing Sat, Feb 7 from San José del Cabo to Chicago, returning Sun, Feb 22, priced at $371 found 2 days ago
Volaris
Mon, Feb 2 - Sun, Feb 8
SJD
San José del Cabo
ORD
Chicago
$371 Roundtrip, found 3 hours ago
$371
Roundtrip
found 3 hours ago
Select Volaris flight, departing Mon, Feb 2 from San José del Cabo to Chicago, returning Sun, Feb 8, priced at $371 found 3 hours ago
Aeromexico
Fri, Aug 29 - Tue, Sep 2
SJD
San José del Cabo
ORD
Chicago
$376 Roundtrip, found 14 hours ago
$376
Roundtrip
found 14 hours ago
Select Aeromexico flight, departing Fri, Aug 29 from San José del Cabo to Chicago, returning Tue, Sep 2, priced at $376 found 14 hours ago
Volaris
Sat, Aug 30 - Wed, Sep 3
SJD
San José del Cabo
ORD
Chicago
$380 Roundtrip, found 9 hours ago
$380
Roundtrip
found 9 hours ago
Select Volaris flight, departing Sat, Aug 30 from San José del Cabo to Chicago, returning Wed, Sep 3, priced at $380 found 9 hours ago
Volaris
Fri, Aug 22 - Sun, Aug 24
SJD
San José del Cabo
ORD
Chicago
$383 Roundtrip, found 5 days ago
$383
Roundtrip
found 5 days ago
Select Volaris flight, departing Fri, Aug 22 from San José del Cabo to Chicago, returning Sun, Aug 24, priced at $383 found 5 days ago
Volaris
Sat, Aug 30 - Wed, Sep 3
SJD
San José del Cabo
ORD
Chicago
$384 Roundtrip, found 9 hours ago
$384
Roundtrip
found 9 hours ago
Select Volaris flight, departing Sat, Aug 30 from San José del Cabo to Chicago, returning Wed, Sep 3, priced at $384 found 9 hours ago
American Airlines
Fri, Aug 1 - Tue, Aug 5
SJD
San José del Cabo
ORD
Chicago
$394 Roundtrip, found 5 hours ago
$394
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Fri, Aug 1 from San José del Cabo to Chicago, returning Tue, Aug 5, priced at $394 found 5 hours ago
Delta
Fri, Aug 29 - Tue, Sep 2
SJD
San José del Cabo
ORD
Chicago
$394 Roundtrip, found 14 hours ago
$394
Roundtrip
found 14 hours ago
Select Delta flight, departing Fri, Aug 29 from San José del Cabo to Chicago, returning Tue, Sep 2, priced at $394 found 14 hours ago

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

June is typically the cheapest month to fly

From $308 - $518 per traveler.

Graph displaying average flight prices per month

Alternative airports near Chicago

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

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $408
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $408
Flights from San José del Cabo (SJD) to Chicago (ORD)
Origin airport
Los Cabos Intl.
Destination airport
O'Hare Intl.
Airlines serving
Aeromexico, Air Canada, Alaska Airlines, American Airlines, Delta, Southwest Airlines, United, Viva, Volaris
Roundtrip price
$346
Distance
1806 mi
Average flight time
6 hours 21 mins

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 July. 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 $196 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.

 

Frequently asked questions

How much does a flight from Los Cabos Intl. Airport (SJD) to O'Hare Intl. Airport (ORD) cost?
Pick up cheap return tickets starting from $393 from Los Cabos Intl. Airport (SJD) to O'Hare Intl. Airport (ORD). 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 SJD on July 24 2025 and touching down at ORD. The price was last updated on July 1 2025 and has not changed since.
What is the cheapest month to fly from SJD to ORD?
Snag a low fare by booking your direct flight from SJD to ORD in July. You can find a one-way American Airlines flight for $216 leaving on July 31 2025. This price is based on the cheapest direct flight found on Expedia for this route in the next 330 days. The price was last updated on July 1 2025 and remains unchanged.
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 SJD to ORD?
Travel from SJD to ORD with American Airlines. This carrier currently has the lowest one-way fare for this route, starting from $216. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from SJD on July 31 2025. Prices were last updated on July 1 2025 and have not changed since.
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.

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