Cheap flights from Oakland (SJC) to Chicago (CHI)

Oakland Metropolitan Oak International (OAK) is a modestly sized international airport offering frequent flights to Chicago Ohare International (ORD). Public transit offers simple and easy access to OAK, with BART running from downtown Oakland, San Francisco and Berkeley directly to the airport. Flights to ORD average 7 to 9 hours.

Upon arrival, grab a cab by heading to the lower-level curb front area next to the baggage claim. Free shuttles to all rental car companies are located outside baggage claim as well. Regional buses also offer rides to further destinations outside of the greater Chicago area.

Attractions and Tips

The Art Institute of Chicago is an internationally celebrated must for art lovers. The Briar Street Theatre, home of the popular performers of the Blue Man Group, is just a half hour drive from ORD and offers exciting live entertainment.

Baseball fans can see the Cubs at the legendary Wrigley Field during baseball season.

Chicago’s weather varies from frigid extremes in the winter months (often accompanied by snow and rain), and warm, but not blistering, in the summer. Visitors who travel during winter should check the status of flights that may be hindered due to snow, rain or ice.

When choosing a hotel, explore the whole city, as many neighborhoods highlight boutique and large chain establishments alike.