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

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

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Route & dates

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

Start: Auckland
Fly:  22​h 30​min
1
New York City
— 13 nights
bus + Fly:  4​h 45​min
2
Chicago
— 12 nights
Fly:  6​h 15​min
3
San Francisco
— 17 nights
Fly:  15​h 30​min
End: Auckland

13
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: explore and take pictures at Central Park, take some stellar pictures from Top of the Rock, admire the landmark architecture of Grand Central Terminal, and take a stroll through Times Square.

To see where to stay, ratings, other places to visit, and more tourist information, use the New York City trip planner .

Auckland, New Zealand to New York City is an approximately 22.5-hour combination of flight and bus. You can also fly; or do a combination of flight and train. You'll gain 17 hours traveling from Auckland to New York City due to the time zone difference. Traveling from Auckland in October, you will find days in New York City are a bit warmer (24°C), and nights are about the same (16°C). Finish up your sightseeing early on the 21st (Mon) so you can travel to Chicago.

Things to do in New York City

Museums Parks Historic Sites

Side Trip

Brooklyn
Highlights from your plan
Central Park ©
Central Park
Empire State Building ©
Empire State Building
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art

12
nights
Chicago

Chicago ©
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 Spas (in Lake Geneva), South Bend (University of Notre Dame, Basilica of the Sacred Heart, & more) and Whirlpool Compass Fountain (in Saint Joseph). There's still lots to do: admire the masterpieces at The Art Institute of Chicago, stroll around Millennium Park, engage your brain at Museum of Science and Industry, and take in panoramic vistas at Skydeck Chicago - Willis Tower.

To find more things to do, where to stay, photos, and tourist information, read our Chicago vacation builder tool .

You can do a combination of bus and flight from New York City to Chicago in 5 hours. Alternatively, you can fly; or drive. The time zone changes from Eastern Standard Time (EST) to Central Standard Time (CST), which is usually a -1 hour difference. Expect a bit cooler temperatures when traveling from New York City in October; daily highs in Chicago reach 21°C and lows reach 11°C. Cap off your sightseeing on the 2nd (Sat) early enough to travel to San Francisco.

Things to do in Chicago

Museums Parks Historic Sites

Side Trips

Oak Park, South Bend, Milwaukee, Wheaton, Rotary Botanical Gardens
Highlights from your plan
Basilica of the Sacred Heart ©
Basilica of the Sacred Heart
The Art Institute of Chicago ©
The Art Institute of Chicago
Museum of Science and Industry ©
Museum of Science and Industry

17
nights
San Francisco

San Francisco is a top holiday destination featuring scenic beauty and great ethnic and cultural diversity.
Explore San Francisco's surroundings by going to Bale Grist Mill State Historic Park (in St. Helena), Muir Woods National Monument (in Mill Valley) and Marina Bay Trail (in Richmond). The adventure continues: take in the views from Golden Gate Bridge, take some stellar pictures from Twin Peaks, wander the streets of SoMa, and engage your brain at Exploratorium.

For maps, more things to do, photos, and tourist information, use the San Francisco online road trip planner .

You can fly from Chicago to San Francisco in 6.5 hours. Other options are to do a combination of flight and train; or drive. The time zone difference moving from Central Standard Time to Pacific Standard Time is minus 2 hours. Traveling from Chicago in November, expect San Francisco to be somewhat warmer, temps between 20°C and 12°C. On the 19th (Tue), you'll travel back home.

Things to do in San Francisco

Parks Neighborhoods Museums

Side Trips

Bale Grist Mill State Historic Park, Occidental Arts and Ecology Center, Marina Bay Trail, Aftel Archive of Curious Scents, Muir Woods National Monument
Highlights from your plan
Beer Tastings & Tours
Golden Gate Bridge ©
Golden Gate Bridge
Alcatraz Island ©
Alcatraz Island

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