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 Silicon Valley and Chicago
Cheapest prices ($59 One Way, $127 Round Trip) found within past 7 days. Prices and availability subject to change. Additional terms may apply.
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.