S$183 Cheap Flights from San Jose to Chicago

View S$183 flight on Mon, 17 Nov, 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$183 for one-way flights and S$427 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Thu, 30 Oct - Wed, 5 Nov
SJC
San Jose
ORD
Chicago
S$427 Return, found 1 day ago
S$427
Return
found 1 day ago
Select Delta flight, departing Thu, 30 Oct from San Jose to Chicago, returning Wed, 5 Nov, priced at S$427 found 1 day ago
United
Thu, 30 Oct - Wed, 5 Nov
SJC
San Jose
ORD
Chicago
S$473 Return, found 1 day ago
S$473
Return
found 1 day ago
Select United flight, departing Thu, 30 Oct from San Jose to Chicago, returning Wed, 5 Nov, priced at S$473 found 1 day ago
United
Thu, 30 Oct - Wed, 5 Nov
SJC
San Jose
ORD
Chicago
S$480 Return, found 1 day ago
S$480
Return
found 1 day ago
Select United flight, departing Thu, 30 Oct from San Jose to Chicago, returning Wed, 5 Nov, priced at S$480 found 1 day ago
United
Thu, 30 Oct - Wed, 5 Nov
SJC
San Jose
ORD
Chicago
S$480 Return, found 1 day ago
S$480
Return
found 1 day ago
Select United flight, departing Thu, 30 Oct from San Jose to Chicago, returning Wed, 5 Nov, priced at S$480 found 1 day ago
Delta
Thu, 30 Oct - Wed, 5 Nov
SJC
San Jose
ORD
Chicago
S$484 Return, found 1 day ago
S$484
Return
found 1 day ago
Select Delta flight, departing Thu, 30 Oct from San Jose to Chicago, returning Wed, 5 Nov, priced at S$484 found 1 day ago
United
Thu, 30 Oct - Wed, 5 Nov
SJC
San Jose
ORD
Chicago
S$485 Return, found 1 day ago
S$485
Return
found 1 day ago
Select United flight, departing Thu, 30 Oct from San Jose to Chicago, returning Wed, 5 Nov, priced at S$485 found 1 day ago
Delta
Thu, 30 Oct - Wed, 5 Nov
SJC
San Jose
ORD
Chicago
S$489 Return, found 1 day ago
S$489
Return
found 1 day ago
Select Delta flight, departing Thu, 30 Oct from San Jose to Chicago, returning Wed, 5 Nov, priced at S$489 found 1 day ago
American Airlines
Thu, 30 Oct - Wed, 5 Nov
SJC
San Jose
ORD
Chicago
S$492 Return, found 1 day ago
S$492
Return
found 1 day ago
Select American Airlines flight, departing Thu, 30 Oct from San Jose to Chicago, returning Wed, 5 Nov, priced at S$492 found 1 day ago
United
Thu, 30 Oct - Wed, 5 Nov
SJC
San Jose
ORD
Chicago
S$523 Return, found 1 day ago
S$523
Return
found 1 day ago
Select United flight, departing Thu, 30 Oct from San Jose to Chicago, returning Wed, 5 Nov, priced at S$523 found 1 day ago
American Airlines
Thu, 30 Oct - Wed, 5 Nov
SJC
San Jose
ORD
Chicago
S$530 Return, found 1 day ago
S$530
Return
found 1 day ago
Select American Airlines flight, departing Thu, 30 Oct from San Jose to Chicago, returning Wed, 5 Nov, priced at S$530 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$132 - S$519 per traveller.

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$427. 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.

Travel information

Travel information

Origin airport
Norman Y. Mineta San Jose Intl.
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, United
Return price
S$427
Distance
2919 km
Average flight time
4 hours 25 mins

Book with confidence

Book with confidence

Perfect flights from San Jose to Chicago

Your Journey from San Jose to Chicago

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With Expedia, you have access to a wide range of airlines, including Delta, American Airlines, United. 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.
 

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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$183 and roundtrip prices from S$427*.
 

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Book Your Flight from San Jose to Chicago with Confidence

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*Note: Prices may vary based on availability and are subject to change.
Perfect flights from San Jose to Chicago

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