26 days in San Francisco & Chicago Itinerary

Created using Inspirock United States visit planner
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1
San Francisco
— 13 nights
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2
Chicago
— 11 nights
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San Francisco — 13 nights

City by the Bay

Explore the numerous day-trip ideas around San Francisco: Charles M. Schulz Museum (in Santa Rosa), Dutton-Goldfield Winery (in Sebastopol) and Healdsburg (Gracianna Winery, Stephen & Walker Winery, &more). Dedicate the 2nd (Mon) to wine at some of the top wineries in the area. The adventure continues: take in the views from Golden Gate Bridge, take a leisurely stroll along Fisherman's Wharf, walk around Golden Gate Park, and see the interesting displays at Exploratorium.

To find where to stay, more things to do, maps, and other tourist information, you can read our San Francisco trip planner.

Melbourne, Australia to San Francisco is an approximately 18.5-hour flight. You'll gain 18 hours traveling from Melbourne to San Francisco due to the time zone difference. In September, San Francisco is somewhat warmer than Melbourne - with highs of 28°C and lows of 17°C. Finish up your sightseeing early on the 6th (Fri) so you can catch the flight to Chicago.
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Wineries · Parks · Neighborhoods · Museums
Side Trips

Chicago — 11 nights

Windy City

Change things up with these side-trips from Chicago: Whiskey Acres Distilling Co. (in DeKalb), South Bend (Grotto of Our Lady Lourdes, Basilica of the Sacred Heart, &more) and Wheaton (Cantigny Park & First Division Museum at Cantigny). The adventure continues: explore the world behind art at The Art Institute of Chicago, take in panoramic vistas at Skydeck Chicago - Willis Tower, get to know the resident critters at Lincoln Park Zoo, and wander the streets of The Magnificent Mile.

For ratings, maps, and other tourist information, go to the Chicago online driving holiday planner.

Traveling by flight from San Francisco to Chicago takes 6 hours. Alternatively, you can drive; or do a combination of subway and train. You'll lose 2 hours traveling from San Francisco to Chicago due to the time zone difference. Prepare for a bit cooler weather when traveling from San Francisco in October: high temperatures in Chicago hover around 21°C and lows are around 11°C. Cap off your sightseeing on the 17th (Tue) early enough to catch the flight back home.
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Museums · Historic Sites · Parks · Childrens Museums
Side Trips