5 days in Continental USA Itinerary

5 days in Continental USA Itinerary

Created using Inspirock Continental USA holiday builder

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Route & dates

5 days in Continental USA Itinerary

Start: Milwaukee
train:  1​h 30​min
1
Chicago
— 1 day
Fly:  6​h 15​min
2
San Francisco
— 1 night
Fly:  8​h 45​min
3
New York City
— 2 nights
Fly:  4​h 45​min
End: Milwaukee

1
day
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Start off your visit on the 17th (Thu): explore and take pictures at Wrigley Field, then get to know the fascinating history of Millennium Park, and then admire the masterpieces at The Art Institute of Chicago.

For reviews, other places to visit, photos, and tourist information, go to the Chicago driving holiday site .

Milwaukee to Chicago is an approximately 1.5-hour train ride. You can also drive; or take a bus. In October, daytime highs in Chicago are 65°F, while nighttime lows are 49°F. Finish your sightseeing early on the 17th (Thu) so you can travel to San Francisco.

Things to do in Chicago

Museums Historic Sites Parks
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Wrigley Field ©
Wrigley Field
Millennium Park ©
Millennium Park

1
night
San Francisco

San Francisco ©
San Francisco is a top holiday destination featuring scenic beauty and great ethnic and cultural diversity.
Kick off your visit on the 18th (Fri): snap pictures at Golden Gate Bridge, then contemplate the long history of SS Jeremiah O'Brien, then take a leisurely stroll along Fisherman's Wharf, and finally head off the coast to Alcatraz Island.

To see photos, reviews, ratings, and other tourist information, read our San Francisco trip itinerary app .

Fly from Chicago to San Francisco in 6.5 hours. Alternatively, you can do a combination of flight and train; or drive. The time zone difference when traveling from Chicago to San Francisco is minus 2 hours. Traveling from Chicago in October, expect San Francisco to be somewhat warmer, temps between 73°F and 56°F. Finish your sightseeing early on the 18th (Fri) so you can travel to New York City.

Things to do in San Francisco

Historic Sites Parks Nature
Highlights from your plan
Alcatraz Island ©
Alcatraz Island
Golden Gate Bridge ©
Golden Gate Bridge
Fisherman's Wharf ©
Fisherman's Wharf

2
nights
New York City

New York City ©
Writer Pearl Buck once called New York City “a place apart,” and this giant urban center remains unlike any other in the world.
New York City is known for museums, nightlife, shopping, historic sites, and parks. Your plan includes some of its best attractions: take in the pleasant sights at Central Park, admire the striking features of Chrysler Building, admire the masterpieces at The Metropolitan Museum of Art, and pause for some photo ops at 9/11 Memorial.

To see reviews, ratings, and more tourist information, you can read our New York City itinerary planner .

Traveling by combination of flight and bus from San Francisco to New York City takes 9 hours. Alternatively, you can fly; or drive. You'll lose 3 hours traveling from San Francisco to New York City due to the time zone difference. October in New York City sees daily highs of 70°F and lows of 57°F at night. Finish your sightseeing early on the 21st (Mon) so you can travel back home.

Things to do in New York City

Parks Museums Historic Sites
Highlights from your plan
Central Park ©
Central Park
Empire State Building ©
Empire State Building
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art

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