Cheap flights from Chicago (CHI) to Silicon Valley (SJC)

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Lowest round trip fares by airline from Chicago and Silicon Valley

Cheapest prices ($53 One Way, $105 Round Trip) found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Great Deals On Cheap Hotels in Silicon Valley

Arena Hotel

Arena Hotel

3 out of 5
817 The Alameda, San Jose, CA
The price is $80 per night from Nov 30 to Nov 30
Situated in San Jose, this hotel is within 1 mi (2 km) of Adobe Corporate Headquarters, SAP Center at San Jose, and San Jose Center for the Performing Arts. ...
3.8/5 Good! (10 reviews)
"Room was a little messy and front desk workers came off as a bit rude. But not a bad experience overall."

Reviewed on Sep 19, 2021

Arena Hotel
Caravelle Inn & Suites

Caravelle Inn & Suites

2 out of 5
1310 N First Street, San Jose, CA
The price is $69 per night from Nov 30 to Nov 30
This family-friendly San Jose motel is located near the airport, within 3 mi (5 km) of Peralta Adobe and Fallon House Historic Site, San Jose State University ...
4.1/5 Very Good! (7 reviews)
"The hotel was very clean and a very good value for the cost. The surrounding hotels are double the cost. Service was very good, only recommendation would be to upgrade their breakfast that the hotel serves each morning."

Reviewed on Mar 29, 2019

Caravelle Inn & Suites
Sterling Inn

Sterling Inn

2 out of 5
2234 The Alameda, Santa Clara, CA
The price is $96 per night from Dec 13 to Dec 13
Situated near the airport, this motel is within 1 mi (2 km) of Mission Santa Clara de Asis and Santa Clara University. SAP Center at San Jose and Winchester ...
4/5 Very Good! (1 review)
"Everything was fine! Hotel was clean for the price, bed and sheets weren’t very comfy but that’s probably the only thing to complain about. The owner was really nice and check in/out was super easy."

Reviewed on Nov 22, 2017

Sterling Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Flights Review

Aug 25, 2019

Cheap tickets was not transparent and clear that the ticket we purchased did not allow even a cabin bag. We will no more purchase ticket thru Cheap Tickets. We had to pay 30$ for a cabin bag which had to be checked in.

A verified traveler
Chicago to San Jose · United
Jul 7, 2018

Great flight!!

A verified traveler
Chicago to San Jose · American Airlines

Fly From Chicago to Silicon Valley

Origin Chicago
Destination Silicon Valley
Number of Daily Flights 59
Earliest Flight Departure Date Dec 6
Latest Flight Departure Date Dec 7
Popular Airlines Alaska Airlines

Cheap flights from Chicago to San Jose

Visitors coming from Chicago to San Jose will have a great time in the unofficial capital of the Silicon Valley. Located 55 miles south of San Francisco, San Jose benefits from its prime location in the Bay area as well as its proximity to the ocean. The San Pedro Square Farmer's Market is a great place to try local produce and the many parks allow for great picnic spots. Tech enthusiasts enjoy visiting the Tech Museum of Innovation while sports fans can attend a San Jose Sharks hockey game or minor league baseball game.

Key Facts

The San Jose International Airport (SJC) is a small airport located only 2 miles northwest of downtown San Jose. Though the downtown region of San Jose is quite compact, attractions in the region are spread out, making a rental car a smart option. To reach downtown from SJC, take Highway 87 south. Visitors also enjoy taking the short drive to San Francisco via Interstate 880.

Hints and Tips

A direct flight from O'Hare International Airport (ORD) to SJC takes about 4 and a half hours. The Rental Car Center at SJC is located across from the baggage claim area, and a shuttle is available to passengers who arrive via Terminal A.

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.