22 days in New York City, Chicago & Washington DC Itinerary

22 days in New York City, Chicago & Washington DC Itinerary

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Route & dates

22 days in New York City, Chicago & Washington DC Itinerary

Start: Florianopolis
Fly:  15​h 45​min
1
New York City
— 5 nights
bus + Fly:  4​h 45​min
2
Chicago
— 5 nights
Fly:  3​h 45​min
3
Washington DC
— 9 nights
Fly:  17​h
End: Florianopolis

5
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.
Let the collections at The Metropolitan Museum of Art and The Museum of Modern Art (MoMA) capture your imagination. You'll explore the less-touristy side of things at Woodbury Common Premium Outlets and Chelsea Market. The adventure continues: take a stroll through Fifth Avenue, take in the pleasant sights at Central Park, enjoy breathtaking views from Empire State Building, and make a trip to Times Square.

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

Florianopolis, Brazil to New York City is an approximately 16-hour flight. You can also do a combination of flight and bus; or do a combination of flight, bus, and train. The time zone difference when traveling from Florianopolis to New York City is minus 2 hours. Traveling from Florianopolis in February, things will get colder in New York City: highs are around 9°C and lows about -1°C. Finish up your sightseeing early on the 7th (Fri) so you can travel to Chicago.

Things to do in New York City

Museums Shopping Historic Sites

Side Trip

Woodbury Common Premium Outlets
Highlights from your plan
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art
9/11 Memorial ©
9/11 Memorial
New York Public Library ©
New York Public Library

5
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
The Magnificent Mile and St. Julian Winery-Union Pier are good opportunities to explore the local culture. You'll explore the less-touristy side of things at Prarie States Winery and Contessa Wine Cellars Tasting Room. You'll find plenty of places to visit near Chicago: John Deere Historic Site (in Grand Detour), The Olive Cart (in Saint Joseph) and Pontiac (Museum of the Gilding Arts, Livingston County Courthouse, & more). And it doesn't end there: explore the world behind art at The Art Institute of Chicago, appreciate the extensive heritage of Millennium Park, engage your brain at Museum of Science and Industry, and do a tasting at DC Estate Winery.

To find photos, other places to visit, and more tourist information, refer to the Chicago trip maker .

Traveling by combination of bus and flight from New York City to Chicago takes 5 hours. Alternatively, you can fly; or drive. You'll gain 1 hour traveling from New York City to Chicago due to the time zone difference. Traveling from New York City in February, things will get little chillier in Chicago: highs are around 2°C and lows about -7°C. Finish your sightseeing early on the 12th (Wed) so you can travel to Washington DC.

Things to do in Chicago

Museums Wineries Shopping

Side Trips

Pontiac, Contessa Wine Cellars Tasting Room, Prairie States Winery, John Deere Historic Site, DC Estate Winery
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
The Magnificent Mile ©
The Magnificent Mile
John Deere Historic Site ©
John Deere Historic Site

9
nights
Washington DC

Washington DC ©
The capital of the United States, the District of Columbia contains the lion's share of the country's most treasured monuments, memorials, and public museums.
Get a sense of the local culture at Gettysburg National Military Park and Desert Rose Ranch & Winery. You'll discover tucked-away gems like The Hague Winery and General's Ridge Vineyard and Winery. Venture out of the city with trips to Gray Ghost Winery (in Amissville), Gettysburg Museum & Visitor Center (in Gettysburg) and R.H. Ballard Shop & Gallery (in Washington). There's much more to do: stroll the grounds of Arlington National Cemetery, do a tasting at Valerie Hill Vineyard & Winery, explore the world behind art at National Gallery of Art, and take an in-depth tour of United States Holocaust Memorial Museum.

For other places to visit, ratings, and more tourist information, you can read our Washington DC tour itinerary builder site .

Getting from Chicago to Washington DC by flight takes about 4 hours. Other options: do a combination of flight and train; or drive. Due to the time zone difference, you'll lose 1 hour traveling from Chicago to Washington DC. Plan for a bit warmer temperatures traveling from Chicago in February, with highs in Washington DC at 10°C and lows at 0°C. You will leave for home on the 21st (Fri).

Things to do in Washington DC

Museums Historic Sites Wineries

Side Trips

Arlington, Gettysburg, Hague, Gray Ghost Winery, Belle Boyd Cottage
Highlights from your plan
Gettysburg National Military Park ©
Gettysburg National Military Park
Arlington National Cemetery ©
Arlington National Cemetery
The Tomb of the Unknown Soldier ©
The Tomb of the Unknown Soldier

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