22 days in New York State & Chicago and Beyond Itinerary

22 days in New York State & Chicago and Beyond Itinerary

Created using Inspirock United States trip planner

Plan created by another user. Make it yours
Fly to John F Kennedy International Airport, Drive to Long Beach
1
Long Beach
— 1 night
Drive
2
Cold Spring
— 3 nights
Drive
3
North Creek
— 2 nights
Drive
4
Niagara Falls
— 2 nights
Fly
5
Chicago
— 3 nights
Fly
6
New York City
— 4 nights
Drive
7
Hampton Bays
— 2 nights
Drive to John F Kennedy International Airport, Fly to King Fahd International Airport

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1
night
Long Beach

Long Beach is a city in Nassau County, New York, United States. On the 26th (Fri), buy something for everyone on your list at Green Acres, admire the majestic nature at Jones Beach State Park, and then tour the pleasant surroundings at Tobay Beach. Keep things going the next day: tour the pleasant surroundings at Long Beach, kick back and relax at Lido Beach, and then walk around Wantagh Park.

To find photos, maps, reviews, and more tourist information, refer to the Long Beach online trip planner.

Dammam, Saudi Arabia to Long Beach is an approximately 21.5-hour combination of flight and car. The time zone changes from Arabian Standard Time (AST) to Eastern Standard Time (EST), which is usually a -8 hour difference. When traveling from Dammam in July, plan for colder days and a bit cooler nights in Long Beach: temperatures range from 34°C by day to 25°C at night. Finish your sightseeing early on the 27th (Sat) so you can travel to Cold Spring.

Things to do in Long Beach

Parks · Outdoors · Beaches · Nature

Side Trips

3
nights
Cold Spring

Cold Spring is a village in the town of Philipstown in Putnam County, New York, United States. Do your shopping at DM Weil Gallery and Rockland Bakery. Escape the urban bustle at Ward Pound Ridge Reservation and Wolf Conservation Center. Get out of town with these interesting Cold Spring side-trips: Angry Orchard (in Walden), Franklin D. Roosevelt Presidential Library and Museum (in Hyde Park) and Sleepy Hollow (Sleepy Hollow Cemetery & Kykuit). And it doesn't end there: get answers to all your questions at Constitution Marsh Audubon Center and Sanctuary, shop like a local with Dia Beacon, browse the fresh offerings at Adams Fairacre Farms, and view the masterpieces at Hudson Beach Glass.

To see maps, traveler tips, reviews, and more tourist information, read Cold Spring trip itinerary website.

Traveling by car from Long Beach to Cold Spring takes 2 hours. Traveling from Long Beach in July, you can expect nighttime temperatures to be slightly colder in Cold Spring, with lows of 21°C. Wrap up your sightseeing on the 30th (Tue) early enough to travel to North Creek.

Things to do in Cold Spring

Parks · Wildlife · Museums · Historic Sites

Side Trips

2
nights
North Creek

North Creek is a census-designated place and hamlet in the Adirondack Park, in the town of Johnsburg, in Warren County, New York, United States. Kick off your visit on the 31st (Wed): Head underground at Natural Stone Bridge and Caves and then learn about all things military at Fort Ticonderoga. Here are some ideas for day two: get outside with Square Eddy Expeditions and then kick back and relax at Moffitt Beach.

To see more things to do, other places to visit, photos, and more tourist information, go to the North Creek online trip planner.

Traveling by car from Cold Spring to North Creek takes 3 hours. Expect slightly colder evenings in North Creek when traveling from Cold Spring in July, with lows around 18°C. Finish up your sightseeing early on the 1st (Thu) so you can travel to Niagara Falls.

Things to do in North Creek

Outdoors · Parks · Historic Sites · Museums

Side Trips

2
nights
Niagara Falls

Honeymoon Capital of the World

The city of Niagara Falls houses the U.S.
Visit Frank Lloyd Wright's Martin House and St. Mary of the Cataract R. C. Parish for their historical value. Escape the urban bustle at Genesee Country Village & Museum and Niagara Jet Adventures. Venture out of the city with trips to Kutter's Cheese Factory Store (in Corfu) and Buffalo & Erie County Naval and Military Park (in Buffalo). The adventure continues: explore the fascinating underground world of Cave of the Winds, enjoy breathtaking views from Niagara Falls Observation Tower, and admire the majestic nature at Devil's Hole State Park.

For more things to do, where to stay, maps, and more tourist information, read our Niagara Falls trip planner.

Traveling by car from North Creek to Niagara Falls takes 5.5 hours. Alternatively, you can do a combination of car and flight. In August in Niagara Falls, expect temperatures between 31°C during the day and 19°C at night. Finish your sightseeing early on the 4th (Sun) so you can travel to Chicago.

Things to do in Niagara Falls

Parks · Outdoors · Museums · Nature

Side Trips

3
nights
Chicago

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Get some historical perspective at Ernest Hemingway Birthplace and Fourth Presbyterian Church. Get a sense of the local culture at The Art Institute of Chicago and Swedish American Museum. Step out of Chicago with an excursion to Rosewood Beach in Highland Park--about 38 minutes away. There's still lots to do: get a taste of the local shopping with The Magnificent Mile, contemplate the long history of Pleasant Home, walk around Jackson Bark - Dog Park, and enjoy breathtaking views from Skydeck Chicago - Willis Tower.

To see maps, where to stay, traveler tips, and tourist information, go to the Chicago day trip planning site.

You can fly from Niagara Falls to Chicago in 5.5 hours. Other options are to drive; or take a train. The time zone difference when traveling from Niagara Falls to Chicago is minus 1 hour. Traveling from Niagara Falls in August, plan for somewhat warmer nights in Chicago, with lows around 22°C. Finish your sightseeing early on the 7th (Wed) to allow enough time to travel to New York City.

Things to do in Chicago

Parks · Museums · Shopping · Neighborhoods

Side Trips

4
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.
Let the collections at 9/11 Memorial and American Museum of Natural History capture your imagination. Get some historical perspective at Ellis Island and Seaport District NYC. There's lots more to do: go for a walk through Times Square, take in the architecture and atmosphere at St. Patrick's Cathedral, explore the world behind art at Frick Collection, and enjoy breathtaking views from Empire State Building.

For reviews, where to stay, more things to do, and tourist information, read our New York City road trip planner.

Traveling by flight from Chicago to New York City takes 5 hours. Alternatively, you can drive; or take a bus. You'll lose 1 hour traveling from Chicago to New York City due to the time zone difference. Expect a daytime high around 34°C in August, and nighttime lows around 25°C. Finish your sightseeing early on the 12th (Mon) so you can drive to Hampton Bays.

Things to do in New York City

Museums · Historic Sites · Neighborhoods · Parks

2
nights
Hampton Bays

Hampton Bays is a hamlet and census-designated place (CDP) in Suffolk County, New York, United States. On the 13th (Tue), step off the mainland to explore Fire Island National Seashore and then tour the pleasant surroundings at Cupsogue Beach County Park. On the 14th (Wed), you'll have a packed day of sightseeing: look for gifts at Hildreth's, enjoy the sand and surf at Cooper's Beach, and then kick back and relax at Ponquogue Beach.

To find reviews, other places to visit, traveler tips, and other tourist information, you can read our Hampton Bays tour planning tool.

Getting from New York City to Hampton Bays by car takes about 2 hours. Other options: take a bus; or take a train. Traveling from New York City in August, Hampton Bays is little chillier at night with lows of 18°C. Wrap up your sightseeing on the 14th (Wed) early enough to travel back home.

Things to do in Hampton Bays

Parks · Outdoors · Beaches · Nature

Side Trips

New York State travel guide

4.5
Observation Decks · Scenic Walking Areas · Monuments
The Empire State
Home to the country's most populous city, the state of New York is a major gateway for immigration into the United States, but also one of the nation's prime holiday destinations. Take a trip down the state's numerous wilderness trails and scenic roads to visit quaint small towns, sandy beaches, historical estates, and artist colonies. Though the majority of visitors head for the big-city restaurants, theaters, and museums, you can venture deeper into the rugged and remote mountain areas to discover a world of picturesque forests, rivers, mountains, and lakes. New York also boasts the nation's largest forest preserve, encompassing much of the northeastern lobe of the state.