19 days in San Francisco & Chicago Itinerary

San Francisco is a top holiday destination featuring scenic beauty and great ethnic and cultural diversity.

Take a break from San Francisco with a short trip to Wine Tours & Tastings in Napa, about 1h 5 min away. There's still lots to do: take in the views from Golden Gate Bridge, step off the mainland to explore Alcatraz Island, explore the world behind art at Asian Art Museum, and take in nature's colorful creations at Japanese Tea Garden.

To see ratings and other tourist information, read San Francisco trip planner.

Manila, Philippines to San Francisco is an approximately 17-hour flight. Traveling from Manila to San Francisco, you'll gain 16 hours due to the time zone difference. Traveling from Manila in May, things will get much colder in San Francisco: highs are around 24°C and lows about 13°C. Wrap up your sightseeing by early afternoon on the 27th (Sat) to allow time for the flight to Chicago.

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.

Chicago is known for sightseeing, museums, and nightlife. Your trip includes some of its best attractions: admire the masterpieces at The Art Institute of Chicago, take a stroll through The Magnificent Mile, admire the local landmark of Buckingham Fountain, and get curious at Museum of Science and Industry.

To find reviews, other places to visit, photos, and other tourist information, read our Chicago day trip planner.

Traveling by flight from San Francisco to Chicago takes 6 hours. Alternatively, you can drive; or do a combination of subway and train. The time zone difference moving from Pacific Standard Time (PST) to Central Standard Time (CST) is 2 hours. In May, plan for daily highs up to 25°C, and evening lows to 13°C. Finish your sightseeing early on the 2nd (Fri) to allow enough time to fly back home.