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

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

Created using Inspirock United States itinerary planner

Plan created by another user.Make it yours

Route & dates

Start: Florianopolis
Fly:  15 h 45 min
1
New York City
— 5 nights
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.
Step off the beaten path and head to Woodbury Common Premium Outlets and Fifth Avenue. You'll explore and learn at The Museum of Modern Art (MoMA) and Frick Collection. The adventure continues: don't miss a visit to The Metropolitan Museum of Art, contemplate the long history of Ellis Island, browse the eclectic array of goods at Chelsea Market, and pause for some serene contemplation at St. Patrick's Cathedral.

For maps, ratings, photos, and tourist information, you can read our New York City online holiday planner.

Florianopolis, Brazil to New York City is an approximately 16-hour flight. You'll gain 2 hours traveling from Florianopolis to New York City due to the time zone difference. Traveling from Florianopolis in February, things will get colder in New York City: highs are around 9°C and lows about -1°C. Finish 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
9/11 Memorial ©
9/11 Memorial
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art
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.
Your cultural itinerary includes sights like The Magnificent Mile and The Art Institute of Chicago. Your inner history buff will appreciate John Deere Historic Site and Livingston County Courthouse. Explore Chicago's surroundings by going to Prairie States Winery (in Genoa), Pontiac (Museum of the Gilding Arts, International Wall Dog Mural and Sign Art Museum, &more) and The Olive Cart (in Saint Joseph). Next up on the itinerary: learn about winemaking at St. Julian Winery & Distillery, get curious at Museum of Science and Industry, and don't miss a visit to Millennium Park.

For where to stay, other places to visit, photos, and more tourist information, read Chicago online trip itinerary maker.

You can fly from New York City to Chicago in 5 hours. Other options are to drive; or take a bus. The time zone difference moving from Eastern Standard Time (EST) to Central Standard Time (CST) is minus 1 hour. Prepare for a bit cooler weather when traveling from New York City in February: high temperatures in Chicago hover around 2°C and lows are around -7°C. Finish up 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, Prairie States Winery, Contessa Wine Cellars Tasting Room, St. Julian Winery & Distillery, 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.
Arlington National Cemetery and The Tomb of the Unknown Soldier will appeal to history buffs. Your cultural itinerary includes sights like National Gallery of Art and Gettysburg National Military Park. Explore the numerous day-trip ideas around Washington DC: Hague (General's Ridge Vineyard and Winery & The Hague Winery), Desert Rose Ranch & Winery (in Hume) and Gettysburg National Military Park Museum & Visitor Center (in Gettysburg). There's still lots to do: learn about winemaking at Gray Ghost Winery, stop by Old Town, contemplate the long history of George Washington's Mount Vernon, and pause for some photo ops at Korean War Veterans Memorial.

For reviews, maps, and tourist information, go to the Washington DC day trip planner.

Fly from Chicago to Washington DC in 4 hours. Alternatively, you can drive; or take a train. The time zone difference moving from Central Standard Time to Eastern Standard Time is 1 hour. 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

Historic Sites Wineries Museums

Side Trips

Hague, Gettysburg, Arlington, Desert Rose Ranch & Winery, R.H. Ballard Shop & Gallery
Highlights from your plan
The Tomb of the Unknown Soldier ©
The Tomb of the Unknown Soldier
Gettysburg National Military Park ©
Gettysburg National Military Park

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