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

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

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Flights from San José del Cabo (SJD) to Chicago (ORD)
Origin airport
Los Cabos Intl.
Destination airport
O'Hare Intl.
Distance
2890 km
Average flight time
5 hours 22 mins

San José del Cabo to Chicago Flights

Whether you’re looking for a grand adventure or just want to get away for a last-minute break, flights from San José del Cabo to Chicago offer the perfect respite. Not only does exploring Chicago provide the chance to make some magical memories, dip into delectable dishes, and tour the local landmarks, but the cheap airfare means you won’t bust your budget. So no matter whether your ideal itinerary involves flying one way, non-stop, or round trip, you’re bound to find flights that match your schedule on Expedia, and at prices that won’t shock your wallet.

Bagging a cheap flight from San José del Cabo to Chicago may mean more dollars to spend on for one-of-a-kind souvenirs when you arrive, but it doesn’t mean you have to skimp on your travel experience, as Expedia offers a sizzling selection of cheap airlines that’ll put you in your happy place on their planes, whether that’s getting lost in a hair-raising airport thriller, dreaming on the passing landscape over a glass of bubbly, or jotting down your vacation bucket list at 38,000 feet. There’s also bound to be plenty of opportunities to snap a few photos of the high life that will make your friends green with envy. After all, enjoying the journey is part of the fun.

With so many affordable flights and so many wonderful adventures awaiting you, there’s no reason to put off booking a fantastic flight from to today. So don’t leave it to the last minute to make your dream trip a reality: pack your bags with your go-to travel accessories, put together your list of must-see attractions and can’t-miss activities, and get ready to broaden your horizons – with Expedia, the wonders of Chicago are only a plane trip away. Book your travel arrangements with us today!

If you would like to book flights to Chicago more flexibly many prefer to purchase one-way tickets with options to take different airlines. A one way ticket to Chicago is now!

Frequently asked questions

How long does it take to fly from Los Cabos Airport to O'Hare Airport?
With American Airlines, a direct flight takes roughly 5 hours and 15 minutes. Lock in a seat on the 11:20AM flight from Los Cabos Intl. Airport (SJD) and touch down at O'Hare Airport at 6:35PM. Pick up an epic deal on this and many other routes when you purchase your ticket with Expedia.
Is it cheaper to buy a plane ticket from SJD to O'Hare Airport last minute?
Booking your journey from Los Cabos Intl. Airport (SJD) to O'Hare Intl. Airport (ORD) last minute could save you dollars if you luck out and find a real steal. However, airfares typically don't come down in price as the departure date nears. If you take a wait-and-see approach, flights could also be booked out or the best seats taken (we hope you like the middle seat!). If you'd rather not hedge your bets, book well in advance of your departure date. Keep in mind that some of the best deals can be found up to 12 months in advance. If your preferred airline hasn't released tickets yet, check back regularly as offers are updated on Expedia constantly.
What airline has the least delays from Los Cabos Airport to O'Hare Intl. Airport (ORD)?
Achieving an on-time rate of 90%, United Airlines is the airline that's most likely to fly you from Los Cabos Airport to O'Hare Airport without any hiccups. Flight delays aren't just frustrating — they can also cause you to miss a connection or even ruin your entire vacation. You can stay updated about delays by checking your flight status through the Expedia App before you even get to the airport. If you're already there and the delay is significant, head to your airline's customer service desk to work out your next move.
What airports do you fly into for Chicago from Cabo San Lucas?
From Cabo San Lucas, you can connect to Chicago through O'Hare Intl. Airport (ORD), Midway Intl. Airport (MDW) and Lewis University Airport (LOT). Find out which hub is the right option for you before you make a decision. If you go with O'Hare Intl. Airport (ORD), it's about 26 kilometers northwest of the center of the city. Use the money you save when booking your ticket with Expedia to explore the city's well-known attractions, such as Wrigley Field and Millennium Park.
What are the most popular departure times for flights from SJD to ORD?
The most popular departure times for trips from SJD to ORD fall between 11:00 AM - 12:00 PM on American Airlines. Our advice is to jet off in the morning. The earlier you fly, the better your chances of arriving on time as air traffic hasn't yet built up around airports.
Can I change the date of my flight from Los Cabos Intl. Airport (SJD) to O'Hare Intl. Airport (ORD)?
We know plans can get upended, so Expedia is here to help make things easier. To start, access your Los Cabos Airport to ORD itinerary through the Expedia Trips portal and browse the ticket conditions and rules about what changes can be made. If you booked your airfare in the last 24 hours, some carriers will let you cancel for free and organize new flights. If you bought your ticket more than 24 hours ago, connect with us through our Customer Service portal so we can assist you further.