28 days in Chicago, New York City & Los Angeles Itinerary

28 days in Chicago, New York City & Los Angeles Itinerary

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Route & dates

28 days in Chicago, New York City & Los Angeles Itinerary

Start: Auckland
Fly:  20​h 15​min
1
Chicago
— 7 nights
Fly + bus:  4​h 45​min
2
New York City
— 8 nights
Fly:  8​h 45​min
3
Los Angeles
— 11 nights
Fly:  15​h 45​min
End: Auckland

7
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Step out of the city life by going to Swallow Cliff Stairs and Cowles Bog. You'll enjoy a bit of beach vacationing at Atwater Park & Beach and Rosewood Beach. Explore Chicago's surroundings by going to Little Red Schoolhouse (in Willow Springs), Hawthorn Hollow - Nature Sanctuary and Arboretum (in Kenosha) and The Course at Aberdeen (in Valparaiso). Next up on the itinerary: cast your line with a fishing tour, identify plant and animal life at Volo Bog State Natural Area, delve into the lush surroundings at Deer Grove Forest Preserve, and don't miss a visit to Millennium Park.

For traveler tips, maps, photos, and tourist information, you can read our Chicago road trip planner .

Auckland, New Zealand to Chicago is an approximately 20.5-hour flight. You can also do a combination of bus and flight. The time zone difference moving from New Zealand Standard Time to Central Standard Time is minus 18 hours. When traveling from Auckland in September, plan for much hotter days in Chicago, with highs around 30°C, while nights are a bit warmer with lows around 19°C. Wrap up your sightseeing on the 1st (Tue) early enough to travel to New York City.

Things to do in Chicago

Outdoors Parks Wildlife

Side Trips

Highland Park, Little Red Schoolhouse, Volo Bog State Natural Area, Atwater Park & Beach, Deer Grove Forest Preserve
Highlights from your plan
Cowles Bog ©
Cowles Bog
Volo Bog State Natural Area ©
Volo Bog State Natural Area
Deer Grove Forest Preserve ©
Deer Grove Forest Preserve

8
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.
Step out of the city life by going to East River Waterfront Esplanade and Speed Boats Tours. Get out of town with these interesting New York City side-trips: Appalachian Trail - Pochuck Boardwalk (in Glenwood), Black Creek Preserve (in Esopus) and Edwin B. Forsythe National Wildlife Refuge (in Oceanville). There's still lots to do: stroll around Central Park, admire the masterpieces at The Metropolitan Museum of Art, explore the landscape on two wheels at Hudson River Greenway, and enjoy breathtaking views from Empire State Building.

To find other places to visit, maps, traveler tips, and more tourist information, read New York City trip itinerary planner .

You can do a combination of flight and bus from Chicago to New York City in 5 hours. Alternatively, you can fly; or drive. The time zone difference moving from Central Standard Time to Eastern Standard Time is 1 hour. Expect somewhat warmer evenings in New York City when traveling from Chicago in October, with lows around 16°C. Wrap up your sightseeing on the 9th (Wed) to allow time to travel to Los Angeles.

Things to do in New York City

Parks Outdoors Wildlife

Side Trips

Edwin B. Forsythe National Wildlife Refuge, Black Creek Preserve, Appalachian Trail - Pochuck Boardwalk
Highlights from your plan
Central Park ©
Central Park
East River Waterfront Esplanade ©
East River Waterfront Esplanade

11
nights
Los Angeles

Surrounded by mountain ranges, forests, valleys, beaches, and deserts, the metropolitan area of Los Angeles is home to over 17 million people.
Relax by the water at Venice Beach and Boardwalk and Santa Monica State Beach. Get in touch with nature at Dolphin & Whale Watching and Self Realization Fellowship Lake Shrine Temple. Explore Los Angeles' surroundings by going to Wood's Cove (in Laguna Beach), Malibu (Nicholas Canyon Beach & Carbon Beach) and Santa Monica Mountains (in Santa Monica). There's lots more to do: immerse yourself in nature at Topanga State Park, take in breathtaking views at Runyon Canyon Park, explore the landscape on two wheels at South Bay Bicycle Trail, and enjoy the sand and surf at Will Rogers State Beach.

For traveler tips, where to stay, photos, and other tourist information, go to the Los Angeles travel itinerary planner .

You can fly from New York City to Los Angeles in 9 hours. Alternatively, you can do a combination of bus and flight; or drive. The time zone difference moving from Eastern Standard Time (EST) to Pacific Standard Time (PST) is minus 3 hours. When traveling from New York City in October, plan for somewhat warmer days and about the same nights in Los Angeles: temperatures range from 32°C by day to 19°C at night. You will have some time to spend on the 20th (Sun) before leaving for home.

Things to do in Los Angeles

Parks Outdoors Beaches

Side Trips

Santa Monica, Malibu, Mulholland Drive, Founder's Park, The Wende Museum of the Cold War
Highlights from your plan
Dolphin & Whale Watching
Venice Beach and Boardwalk ©
Venice Beach and Boardwalk
Santa Monica Mountains ©
Santa Monica Mountains

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