5 days in United States Itinerary

5 days in United States Itinerary

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Route & dates

5 days in United States Itinerary

Start: Chicago
Fly:  5​h 45​min
1
Key West
— 2 nights
Fly + bus:  6​h
2
New York City
— 1 night
Fly + bus:  5​h 30​min
3
Niagara Falls
— 1 night
bus + Fly:  4​h 45​min
End: Chicago

2
nights
Key West

Located just 140 km (90 mi) from Cuba, Key West is an island only about 6.4 km (4 mi) long and 1.6 km (1 mi) wide.
On your second day here, get up close to creatures of the deep with a dolphin and whale watching tour, then steep yourself in history at Truman Little White House, and then admire the majestic nature at Fort Zachary Taylor.

For more things to do, traveler tips, other places to visit, and other tourist information, go to the Key West online tour planner .

Chicago to Key West is an approximately 6-hour flight. You can also drive; or do a combination of bus and shuttle. Due to the time zone difference, you'll lose 1 hour traveling from Chicago to Key West. Traveling from Chicago in September, things will get somewhat warmer in Key West: highs are around 88°F and lows about 80°F. Finish your sightseeing early on the 19th (Thu) to allow enough time to travel to New York City.

Things to do in Key West

Outdoors Wildlife Tours
Highlights from your plan
Dolphin & Whale Watching
Fort Zachary Taylor ©
Fort Zachary Taylor
Fishing Charters & Tours

1
night
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.
Start off your visit on the 20th (Fri): admire the masterpieces at The Metropolitan Museum of Art, wander the streets of Times Square, and then pause for some photo ops at 9/11 Memorial.

To find other places to visit, more things to do, traveler tips, and other tourist information, go to the New York City holiday planner.

You can do a combination of flight and bus from Key West to New York City in 6 hours. Alternatively, you can fly; or drive. Traveling from Key West in September, expect New York City to be a bit cooler, temps between 80°F and 66°F. Wrap up your sightseeing on the 20th (Fri) to allow time to travel to Niagara Falls.

Things to do in New York City

Museums Historic Sites Neighborhoods
Highlights from your plan
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art
9/11 Memorial ©
9/11 Memorial
Times Square ©
Times Square

1
night
Niagara Falls

Niagara Falls ©
The city of Niagara Falls houses the U.S.
On the 21st (Sat), take in the dramatic scenery at Bridal Veil Falls, then take in panoramic vistas at Niagara Falls Observation Tower, then explore the fascinating underground world of Cave of the Winds, and finally take in the dramatic scenery at Niagara Falls.

For maps, ratings, and tourist information, refer to the Niagara Falls holiday site .

You can do a combination of flight and bus from New York City to Niagara Falls in 5.5 hours. Alternatively, you can do a combination of bus and flight; or drive. Traveling from New York City in September, expect Niagara Falls to be little chillier, temps between 75°F and 55°F. Wrap up your sightseeing on the 21st (Sat) to allow time to travel back home.

Things to do in Niagara Falls

Parks Nature
Highlights from your plan
Cave of the Winds ©
Cave of the Winds
Niagara Falls ©
Niagara Falls
Bridal Veil Falls ©
Bridal Veil Falls

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