S$165 Cheap Flights from Chicago to San Jose

View S$165 flight on Fri, 29 Aug, 2025Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Norman Y. Mineta San Jose Intl. Airport (SJC)

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Cheap Flights from Chicago to San Jose (ORD-SJC)

Prices were available within the past 7 days and start at S$165 for one-way flights and S$351 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Mon, 18 Aug - Mon, 25 Aug
ORD
Chicago
SJC
San Jose
S$351 Return, found 3 days ago
S$351
Return
found 3 days ago
Select Delta flight, departing Mon, 18 Aug from Chicago to San Jose, returning Mon, 25 Aug, priced at S$351 found 3 days ago
Delta
Thu, 7 Aug - Wed, 13 Aug
ORD
Chicago
SJC
San Jose
S$367 Return, found 2 days ago
S$367
Return
found 2 days ago
Select Delta flight, departing Thu, 7 Aug from Chicago to San Jose, returning Wed, 13 Aug, priced at S$367 found 2 days ago
Delta
Thu, 7 Aug - Wed, 13 Aug
ORD
Chicago
SJC
San Jose
S$406 Return, found 2 days ago
S$406
Return
found 2 days ago
Select Delta flight, departing Thu, 7 Aug from Chicago to San Jose, returning Wed, 13 Aug, priced at S$406 found 2 days ago
United
Thu, 7 Aug - Wed, 13 Aug
ORD
Chicago
SJC
San Jose
S$413 Return, found 2 days ago
S$413
Return
found 2 days ago
Select United flight, departing Thu, 7 Aug from Chicago to San Jose, returning Wed, 13 Aug, priced at S$413 found 2 days ago
Delta
Sun, 17 Aug - Sun, 24 Aug
ORD
Chicago
SJC
San Jose
S$417 Return, found 2 days ago
S$417
Return
found 2 days ago
Select Delta flight, departing Sun, 17 Aug from Chicago to San Jose, returning Sun, 24 Aug, priced at S$417 found 2 days ago
United
Thu, 7 Aug - Wed, 13 Aug
ORD
Chicago
SJC
San Jose
S$425 Return, found 2 days ago
S$425
Return
found 2 days ago
Select United flight, departing Thu, 7 Aug from Chicago to San Jose, returning Wed, 13 Aug, priced at S$425 found 2 days ago
Delta
Thu, 7 Aug - Wed, 13 Aug
ORD
Chicago
SJC
San Jose
S$431 Return, found 2 days ago
S$431
Return
found 2 days ago
Select Delta flight, departing Thu, 7 Aug from Chicago to San Jose, returning Wed, 13 Aug, priced at S$431 found 2 days ago
Delta
Mon, 18 Aug - Mon, 25 Aug
ORD
Chicago
SJC
San Jose
S$435 Return, found 3 days ago
S$435
Return
found 3 days ago
Select Delta flight, departing Mon, 18 Aug from Chicago to San Jose, returning Mon, 25 Aug, priced at S$435 found 3 days ago
Delta
Thu, 7 Aug - Wed, 13 Aug
ORD
Chicago
SJC
San Jose
S$444 Return, found 2 days ago
S$444
Return
found 2 days ago
Select Delta flight, departing Thu, 7 Aug from Chicago to San Jose, returning Wed, 13 Aug, priced at S$444 found 2 days ago
American Airlines
Thu, 7 Aug - Wed, 13 Aug
ORD
Chicago
SJC
San Jose
S$476 Return, found 2 days ago
S$476
Return
found 2 days ago
Select American Airlines flight, departing Thu, 7 Aug from Chicago to San Jose, returning Wed, 13 Aug, priced at S$476 found 2 days ago

Find the cheapest month to fly from Chicago (ORD) to San Jose (SJC)

September is typically the cheapest month to fly

From S$124 - S$420 per traveller.

Graph displaying average flight prices per month

Chicago to San Jose route information
Origin airport
O'Hare Intl.
Destination airport
Norman Y. Mineta San Jose Intl.
Airlines serving
American Airlines, Delta, United
Return price
S$350
Distance
2919 km
Average flight time
4 hours 56 mins

Perfect flights from Chicago to San Jose

Your Journey from Chicago to San Jose

Start your unforgettable journey with Expedia. Our broad selection of flights from Chicago to San Jose caters to every travel need. Whether you're yearning for a romantic escape, a solo adventure, or a cultural immersion, we've got you covered.
 

Choosing Your Ideal Flight

With Expedia, you have access to a wide range of airlines, including Delta, United, American Airlines. Our selection of flights from O'Hare Intl. to Norman Y. Mineta San Jose Intl. caters to every traveler's requirements, ensuring your journey aligns with your schedule. With options from 20 airlines, you're bound to find the perfect flight.
 

Maximizing Value with Chicago to San Jose Flights

Experience the joy of finding cheap flights from O'Hare Intl. to Norman Y. Mineta San Jose Intl. that fit your budget. Keep an eye out for our special deals and discounts, and check our flexible one-way fares from S$165 and roundtrip prices from S$351*.
 

Pre-Flight Essentials

Ensure a smooth journey from Chicago to San Jose with Expedia. From information about check-in times and in-flight amenities to guidance on baggage policies, we provide all the essentials to prepare you for your flight.
 

Experience the Vibrant San Jose

Picture yourself stepping off the plane in San Jose and immersing yourself in the unique atmosphere of San Jose. From local markets to cultural festivals, each city offers its distinct charm. Make the most of your trip by exploring local attractions and indulging in the local cuisine. With Expedia, explore all this and more, tailored to your budget.
 

Added Convenience on Your Chicago to San Jose Flight

Traveling with Expedia is more than just a flight. We offer details about in-flight amenities, baggage policies, and more to ensure a smooth and hassle-free journey. Choose from our variety of airlines and embark on a memorable journey from Chicago to San Jose.
 

Beyond the Flight – Exploring San Jose

With Expedia, your adventure extends beyond the flight. Explore San Jose at your own pace by renting a car or booking a hotel. Discover hidden gems off the beaten path and create unforgettable memories.
 

Book Your Flight from Chicago to San Jose with Confidence

Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support make your travel experience seamless and stress-free. Embark on your journey from Chicago to San Jose with confidence. Book your travel arrangements with Expedia today.
 
*Note: Prices may vary based on availability and are subject to change.

Frequently asked questions

How much is a flight from O'Hare Intl. Airport (ORD) to SJC?
Pack your bags, because round-trip flights from ORD to San Jose Intl. Airport start from S$351. That's based on fares listed within the last 7 days on Expedia for flights departing within the next year. Prices can change quickly, so book now to lock in the best deal. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from ORD to Norman Y. Mineta San Jose Intl. Airport (SJC)?
This varies between airlines, as each has its own terms and conditions. Visit the Customer Service Portal, where you'll find easy instructions on how to cancel online.
How do I find cheap flights from ORD to SJC 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 O'Hare Intl. Airport (ORD) to Norman Y. Mineta San Jose Intl. Airport (SJC) flights, you'll see a "no change fees" filter for you to select.
How far is the flight from ORD to SJC?
The flying distance between O'Hare Intl. Airport (ORD) (ORD) and SJC (SJC) is 2,900 kilometres. Sneak in a nap or get stuck into a book and the journey will zip on by.
Which airlines fly direct from ORD to San Jose Intl. Airport?
Operating 30 flights monthly, United Airlines (UA) is a great choice when flying directly from O'Hare Intl. Airport (ORD) to Norman Y. Mineta San Jose Intl. Airport (SJC).
Are ORD to San Jose Intl. Airport flight tickets cheaper when they're purchased at the last minute?
Booking your trip from O'Hare Intl. Airport (ORD) to San Jose Intl. Airport at the last minute could save you some serious cash. However, it might cost you a whole lot more! If you'd rather play it safe, book well ahead of your departure date. In fact, Expedia has some of the biggest bargains as far ahead as 12 months in advance. If your preferred air carrier hasn't released tickets yet, check back regularly as deals are updated on Expedia all the time.

Explore a world of travel with Expedia

San Jose Airports

San Francisco

Chicago to San Francisco Intl.
S$327.80

Oakland

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Chicago

Midway Intl. to San Jose
S$417.00
*Available to Expedia members.