S$140 Cheap Flights from San Jose to Chicago

View S$140 flight on Sat, 30 Aug, 2025Opens in a new window

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

  • 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$140 for one-way flights and S$272 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sat, 23 Aug - Tue, 26 Aug
SJC
San Jose
ORD
Chicago
S$272 Return, found 3 hours ago
S$272
Return
found 3 hours ago
Select Delta flight, departing Sat, 23 Aug from San Jose to Chicago, returning Tue, 26 Aug, priced at S$272 found 3 hours ago
Delta
Sat, 23 Aug - Tue, 26 Aug
SJC
San Jose
ORD
Chicago
S$297 Return, found 3 hours ago
S$297
Return
found 3 hours ago
Select Delta flight, departing Sat, 23 Aug from San Jose to Chicago, returning Tue, 26 Aug, priced at S$297 found 3 hours ago
Delta
Sat, 23 Aug - Tue, 26 Aug
SJC
San Jose
ORD
Chicago
S$304 Return, found 3 hours ago
S$304
Return
found 3 hours ago
Select Delta flight, departing Sat, 23 Aug from San Jose to Chicago, returning Tue, 26 Aug, priced at S$304 found 3 hours ago
Delta
Sat, 23 Aug - Tue, 26 Aug
SJC
San Jose
ORD
Chicago
S$304 Return, found 3 hours ago
S$304
Return
found 3 hours ago
Select Delta flight, departing Sat, 23 Aug from San Jose to Chicago, returning Tue, 26 Aug, priced at S$304 found 3 hours ago
American Airlines
Sat, 23 Aug - Tue, 26 Aug
SJC
San Jose
ORD
Chicago
S$310 Return, found 3 hours ago
S$310
Return
found 3 hours ago
Select American Airlines flight, departing Sat, 23 Aug from San Jose to Chicago, returning Tue, 26 Aug, priced at S$310 found 3 hours ago
Delta
Sat, 23 Aug - Tue, 26 Aug
SJC
San Jose
ORD
Chicago
S$316 Return, found 3 hours ago
S$316
Return
found 3 hours ago
Select Delta flight, departing Sat, 23 Aug from San Jose to Chicago, returning Tue, 26 Aug, priced at S$316 found 3 hours ago
United
Sat, 23 Aug - Tue, 26 Aug
SJC
San Jose
ORD
Chicago
S$327 Return, found 3 hours ago
S$327
Return
found 3 hours ago
Select United flight, departing Sat, 23 Aug from San Jose to Chicago, returning Tue, 26 Aug, priced at S$327 found 3 hours ago
Delta
Fri, 22 Aug - Fri, 29 Aug
SJC
San Jose
ORD
Chicago
S$328 Return, found 1 day ago
S$328
Return
found 1 day ago
Select Delta flight, departing Fri, 22 Aug from San Jose to Chicago, returning Fri, 29 Aug, priced at S$328 found 1 day ago
Delta
Sat, 23 Aug - Tue, 26 Aug
SJC
San Jose
ORD
Chicago
S$329 Return, found 3 hours ago
S$329
Return
found 3 hours ago
Select Delta flight, departing Sat, 23 Aug from San Jose to Chicago, returning Tue, 26 Aug, priced at S$329 found 3 hours ago
United
Sat, 23 Aug - Tue, 26 Aug
SJC
San Jose
ORD
Chicago
S$336 Return, found 3 hours ago
S$336
Return
found 3 hours ago
Select United flight, departing Sat, 23 Aug from San Jose to Chicago, returning Tue, 26 Aug, priced at S$336 found 3 hours 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.
Airlines serving
American Airlines, Delta, United
Return price
S$272
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. 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$140 and roundtrip prices from S$272*.
 

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$272. 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

Chicago Airports

Chicago

San Jose Airports

San Francisco

San Francisco Intl. to Chicago
S$249.10

Oakland

Oakland Intl. to Chicago
S$328.90
*Available to Expedia members.