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

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Lowest round trip fares by airline from Silicon Valley and Chicago

Cheapest prices ($55 One Way, $127 Round Trip) found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Fly From Silicon Valley to Chicago

Origin
Silicon Valley
Destination
Chicago
Number of Daily Flights
61
Earliest Flight Departure Date
Mar 18
Latest Flight Departure Date
Mar 19
Popular Airlines
Hawaiian Airlines

Cheap flights from San Jose to Chicago

After your flight from San Jose, you'll want to rent a car to see all of Chicago properly. From the airport, you can easily reach downtown by taking I-90 or I-94. Once downtown, you can bask in front of famous paintings in the Art Institute, catch a concert by the magnificent Chicago Symphony Orchestra or pose by Cloud Gate, a sculpture that's also nicknamed "The Bean" for its shape.

Key Facts

Chicago is a sports-centered city where you can catch a match by any major league sport; the Bulls, Blackhawks, Fire, White Sox and Cubs all call Chicago home. If sports don't excite you, take a leisurely walk along Lake Michigan on the Lakefront Trail, see animals at the free Lincoln Park Zoo, or have some laughs at a Second City performance. Foodies can appreciate authentic Mexican food in the Pilsen neighborhood, or a deep-dish pizza from one of the many pizzerias.

Hints and Tips

The flight from San Jose International Airport (SJC) to Chicago takes about five hours. Because Chicago O'Hare International Airport (ORD) is a major transportation hub, you can easily catch a connecting flight. If you have a long layover, head for Navy Pier to relax and check out the view.

*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.