44 days in New York City, Chicago & San Francisco Itinerary

44 days in New York City, Chicago & San Francisco Itinerary

Created using Inspirock United States itinerary planner

Plan created by another user. Make it yours
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1
New York City
— 13 nights
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Chicago
— 12 nights
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3
San Francisco
— 17 nights
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13
nights
New York City

Big Apple

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, and shopping. Your plan includes some of its best attractions: stroll around Central Park, go for a walk through The High Line, admire the landmark architecture of Grand Central Terminal, and browse the exhibits of 9/11 Memorial.

To find where to stay, photos, reviews, and more tourist information, go to the New York City trip itinerary builder.

Auckland, New Zealand to New York City is an approximately 19.5-hour flight. You'll gain 17 hours traveling from Auckland to New York City due to the time zone difference. Expect somewhat warmer weather when traveling from Auckland in October: highs in New York City hover around 24°C, while lows dip to 16°C. Finish your sightseeing early on the 21st (Mon) to allow enough time to travel to Chicago.

Things to do in New York City

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Central Park ©
Must see
Central Park
4.8

12
nights
Chicago

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Venture out of the city with trips to South Bend (University of Notre Dame, Basilica of the Sacred Heart, &more), Whirlpool Compass Fountain (in Saint Joseph) and Spas (in Lake Geneva). The adventure continues: explore the world behind art at The Art Institute of Chicago, admire the landmark architecture of Skydeck Chicago - Willis Tower, contemplate the long history of Ernest Hemingway Birthplace, and visit The Magnificent Mile.

For more things to do, photos, reviews, and tourist information, read our Chicago trip planner.

Traveling by flight from New York City to Chicago takes 5 hours. Alternatively, you can drive; or take a bus. The time zone difference when traveling from New York City to Chicago is minus 1 hour. Prepare for a bit cooler weather when traveling from New York City in October: high temperatures in Chicago hover around 21°C and lows are around 11°C. Wrap up your sightseeing on the 2nd (Sat) early enough to travel to San Francisco.

Things to do in Chicago

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17
nights
San Francisco

City by the Bay

San Francisco is a top holiday destination featuring scenic beauty and great ethnic and cultural diversity.
Change things up with these side-trips from San Francisco: Bale Grist Mill State Historic Park (in St. Helena), Muir Woods National Monument (in Mill Valley) and Marina Bay Trail (in Richmond). There's still lots to do: snap pictures at Golden Gate Bridge, see the interesting displays at Exploratorium, wander the streets of SoMa, and take some stellar pictures from Twin Peaks.

To see photos, reviews, other places to visit, and tourist information, go to the San Francisco online trip builder.

You can fly from Chicago to San Francisco in 6.5 hours. Other options are to drive; or do a combination of train and subway. The time zone changes from Central Standard Time to Pacific Standard Time, which is usually a -2 hour difference. Traveling from Chicago in November, expect San Francisco to be a bit warmer, temps between 20°C and 12°C. You will leave for home on the 19th (Tue).

Things to do in San Francisco

Parks · Neighborhoods · Museums · Outdoors

Side Trips

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