S$214 Cheap Flights from San Jose to Chicago

View S$214 flight on Wed, 14 May,2025Opens in a new window

Featured airlines

Singapore Airlines
AirAsia
Scoot
Philippine Airlines
Malaysia Airlines
Thai Airways International
Asiana Airlines
Qatar Airways
Air India

  • Plan, book, fly with confidence

  • trending down icon
    Be in the know
    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon
    Book smarter
    Save up to 40% on select hotels after you book a flight*
  • payments icon
    Earn twice
    Earn your airline miles on top of our rewards
    Sign in

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

Prices were available within the past 7 days and start at S$214 for one-way flights and S$450 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, 13 May - Wed, 14 May
SJC
San Jose
ORD
Chicago
S$450 Return, found 3 days ago
S$450
Return
found 3 days ago
Select Delta flight, departing Tue, 13 May from San Jose to Chicago, returning Wed, 14 May, priced at S$450 found 3 days ago
Delta
Tue, 13 May - Thu, 15 May
SJC
San Jose
ORD
Chicago
S$473 Return, found 3 days ago
S$473
Return
found 3 days ago
Select Delta flight, departing Tue, 13 May from San Jose to Chicago, returning Thu, 15 May, priced at S$473 found 3 days ago
Delta
Tue, 13 May - Sat, 17 May
SJC
San Jose
ORD
Chicago
S$475 Return, found 3 days ago
S$475
Return
found 3 days ago
Select Delta flight, departing Tue, 13 May from San Jose to Chicago, returning Sat, 17 May, priced at S$475 found 3 days ago
Delta
Thu, 15 May - Sat, 17 May
SJC
San Jose
ORD
Chicago
S$500 Return, found 3 days ago
S$500
Return
found 3 days ago
Select Delta flight, departing Thu, 15 May from San Jose to Chicago, returning Sat, 17 May, priced at S$500 found 3 days ago
Delta
Tue, 13 May - Fri, 16 May
SJC
San Jose
ORD
Chicago
S$506 Return, found 3 days ago
S$506
Return
found 3 days ago
Select Delta flight, departing Tue, 13 May from San Jose to Chicago, returning Fri, 16 May, priced at S$506 found 3 days ago
Delta
Tue, 13 May - Sun, 25 May
SJC
San Jose
ORD
Chicago
S$516 Return, found 3 days ago
S$516
Return
found 3 days ago
Select Delta flight, departing Tue, 13 May from San Jose to Chicago, returning Sun, 25 May, priced at S$516 found 3 days ago
Delta
Tue, 13 May - Fri, 23 May
SJC
San Jose
ORD
Chicago
S$528 Return, found 3 days ago
S$528
Return
found 3 days ago
Select Delta flight, departing Tue, 13 May from San Jose to Chicago, returning Fri, 23 May, priced at S$528 found 3 days ago
Delta
Thu, 15 May - Sat, 17 May
SJC
San Jose
ORD
Chicago
S$530 Return, found 3 days ago
S$530
Return
found 3 days ago
Select Delta flight, departing Thu, 15 May from San Jose to Chicago, returning Sat, 17 May, priced at S$530 found 3 days ago
Delta
Fri, 16 May - Sat, 17 May
SJC
San Jose
ORD
Chicago
S$533 Return, found 3 days ago
S$533
Return
found 3 days ago
Select Delta flight, departing Fri, 16 May from San Jose to Chicago, returning Sat, 17 May, priced at S$533 found 3 days ago
Delta
Sun, 18 May - Wed, 21 May
SJC
San Jose
ORD
Chicago
S$540 Return, found 3 days ago
S$540
Return
found 3 days ago
Select Delta flight, departing Sun, 18 May from San Jose to Chicago, returning Wed, 21 May, priced at S$540 found 3 days ago
San Jose to Chicago route information
Origin airport
Norman Y. Mineta San Jose Intl.
Destination airport
O'Hare Intl.
Return price
S$449
Distance
2919 km

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. 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$214 and roundtrip prices from S$450*.
 

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 Chicago. 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$450. 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.
*Available to Expedia members.