S$165 Cheap Flights from San Jose to Chicago

View S$165 flight on Wed, 20 Aug, 2025Opens in a new window

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

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

Prices were available within the past 7 days and start at S$165 for one-way flights and S$1,440 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Fri, 11 Jul - Sat, 12 Jul
SJC
San Jose
ORD
Chicago
S$1,440 Return, found 1 day ago
S$1,440
Return
found 1 day ago
Select United flight, departing Fri, 11 Jul from San Jose to Chicago, returning Sat, 12 Jul, priced at S$1,440 found 1 day ago
United
Fri, 11 Jul - Sat, 12 Jul
SJC
San Jose
ORD
Chicago
S$1,446 Return, found 1 day ago
S$1,446
Return
found 1 day ago
Select United flight, departing Fri, 11 Jul from San Jose to Chicago, returning Sat, 12 Jul, priced at S$1,446 found 1 day ago
Delta
Fri, 11 Jul - Sat, 12 Jul
SJC
San Jose
ORD
Chicago
S$1,452 Return, found 1 day ago
S$1,452
Return
found 1 day ago
Select Delta flight, departing Fri, 11 Jul from San Jose to Chicago, returning Sat, 12 Jul, priced at S$1,452 found 1 day ago
United
Fri, 11 Jul - Sat, 12 Jul
SJC
San Jose
ORD
Chicago
S$1,452 Return, found 1 day ago
S$1,452
Return
found 1 day ago
Select United flight, departing Fri, 11 Jul from San Jose to Chicago, returning Sat, 12 Jul, priced at S$1,452 found 1 day ago
American Airlines
Fri, 11 Jul - Sat, 12 Jul
SJC
San Jose
ORD
Chicago
S$1,457 Return, found 1 day ago
S$1,457
Return
found 1 day ago
Select American Airlines flight, departing Fri, 11 Jul from San Jose to Chicago, returning Sat, 12 Jul, priced at S$1,457 found 1 day ago
Delta
Fri, 11 Jul - Sat, 12 Jul
SJC
San Jose
ORD
Chicago
S$1,457 Return, found 1 day ago
S$1,457
Return
found 1 day ago
Select Delta flight, departing Fri, 11 Jul from San Jose to Chicago, returning Sat, 12 Jul, priced at S$1,457 found 1 day ago
Delta
Fri, 11 Jul - Sat, 12 Jul
SJC
San Jose
ORD
Chicago
S$1,459 Return, found 1 day ago
S$1,459
Return
found 1 day ago
Select Delta flight, departing Fri, 11 Jul from San Jose to Chicago, returning Sat, 12 Jul, priced at S$1,459 found 1 day ago
United
Fri, 11 Jul - Sat, 12 Jul
SJC
San Jose
ORD
Chicago
S$1,465 Return, found 1 day ago
S$1,465
Return
found 1 day ago
Select United flight, departing Fri, 11 Jul from San Jose to Chicago, returning Sat, 12 Jul, priced at S$1,465 found 1 day ago
United
Fri, 11 Jul - Sat, 12 Jul
SJC
San Jose
ORD
Chicago
S$1,669 Return, found 1 day ago
S$1,669
Return
found 1 day ago
Select United flight, departing Fri, 11 Jul from San Jose to Chicago, returning Sat, 12 Jul, priced at S$1,669 found 1 day ago
Alaska Airlines
Fri, 11 Jul - Sat, 12 Jul
SJC
San Jose
ORD
Chicago
S$1,801 Return, found 1 day ago
S$1,801
Return
found 1 day ago
Select Alaska Airlines flight, departing Fri, 11 Jul from San Jose to Chicago, returning Sat, 12 Jul, priced at S$1,801 found 1 day ago

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

February is typically the cheapest month to fly

From S$115 - S$538 per traveller.

Graph displaying average flight prices per month

San Jose to Chicago route information
Origin airport
Norman Y. Mineta San Jose Intl.
Destination airport
O'Hare Intl.
Return price
S$1,439
Distance
2919 km
Average flight time
4 hours 22 mins

Perfect flights from San Jose to Chicago

Your Journey from San Jose to Chicago

Start your unforgettable journey with Expedia. Our broad selection of flights from San Jose to Chicago 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, Alaska Airlines. Our selection of flights from Norman Y. Mineta San Jose Intl. to O'Hare 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 San Jose to Chicago Flights

Experience the joy of finding cheap flights from Norman Y. Mineta San Jose Intl. to O'Hare 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$1,440*.
 

Pre-Flight Essentials

Ensure a smooth journey from San Jose to Chicago 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 Chicago

Picture yourself stepping off the plane in Chicago and immersing yourself in the unique atmosphere of . 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 San Jose to Chicago 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 San Jose to Chicago.
 

Beyond the Flight – Exploring Chicago

With Expedia, your adventure extends beyond the flight. Explore Chicago 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 San Jose to Chicago 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 San Jose to Chicago 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 SJC to O'Hare Airport?
Round-trip journeys from SJC to O'Hare Intl. Airport (ORD) start from S$1,440. This price is based on fares listed within the last 7 days on Expedia for flights departing within the next year --- make your booking ASAP to avoid missing out. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from San Jose Intl. Airport to O'Hare Intl. Airport (ORD)?
Most flights can be cancelled online, but every airline has a different set of terms and conditions. If you do have to cancel your flight, check out our Customer Service Portal and follow the instructions.
How do I find cheap flights from SJC to O'Hare Airport 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 SJC to ORD flights, you'll see a "no change fees" filter for you to select.
How far is the flight from SJC to ORD?
The flight distance between SJC and ORD is 2,900 kilometres. Pack yourself a drink, a few snacks and an interesting book to read. Keep yourself occupied and the hours will zip by.
Which airlines fly direct from Norman Y. Mineta San Jose Intl. Airport (SJC) to ORD?
Operating 30 flights every month, United Airlines (UA) is a great choice when flying directly from San Jose Intl. Airport to O'Hare Airport.
Are Norman Y. Mineta San Jose Intl. Airport (SJC) to O'Hare Airport flight tickets cheaper when they're purchased at the last minute?
Late planners can sometimes nab a bargain, with some super cheap airfares from Norman Y. Mineta San Jose Intl. Airport (SJC) to O'Hare Airport arising a few weeks prior to the departure date. If you'd rather plan ahead, Expedia compares and updates the best flight deals continually --- as early as a year in advance in some cases. It does depend on the carrier though, as not all airlines publish prices that far in advance.

Explore a world of travel with Expedia

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