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

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

Created using Inspirock United States itinerary planner

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Route & dates

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

Start: Vero Beach
Drive:  15​h 15​min
1
Washington DC
— 3 nights
Drive:  4​h 30​min
2
New York City
— 5 nights
Drive:  13​h 15​min
3
Chicago
— 4 nights
Drive:  15​h 30​min
End: Vero Beach

3
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.
Your list of things to see and do now includes Harpers Ferry National Historical Park, National World War II Memorial, National Gallery of Art - Sculpture Garden, and other attractions. Eschew the tourist crowds and head to Great Falls Park and Vietnam Veterans Memorial. The adventure continues: wander the streets of Georgetown, get to know the fascinating history of Capitol Hill, and pause for some photo ops at Lincoln Memorial.

For where to stay, traveler tips, maps, and other tourist information, refer to the Washington DC trip itinerary builder website .

Vero Beach to Washington DC is an approximately 6.5-hour combination of bus and flight. You can also do a combination of shuttle and flight; or drive. In June, plan for daily highs up to 86°F, and evening lows to 69°F. Wrap up your sightseeing on the 4th (Tue) to allow time to travel to New York City.

Things to do in Washington DC

Parks Nature Historic Sites

Side Trips

Great Falls Park, Harpers Ferry National Historical Park
Highlights from your plan
Georgetown ©
Georgetown
Great Falls Park ©
Great Falls Park

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.
Your day-by-day itinerary now includes New York Media Boat / Adventure Sightseeing Tours, Foods of New York Tours, Brooklyn Botanic Garden, and other attractions you added. Shop till you drop at Chelsea Market and SoHo. Next up on the itinerary: take a stroll through Times Square, take in the pleasant sights at Central Park, make a trip to Empire State Building, and admire all the interesting features of Madison Square Garden.

For photos, traveler tips, where to stay, and more tourist information, read New York City trip planner .

You can fly from Washington DC to New York City in 3.5 hours. Alternatively, you can take a train; or drive. Traveling from Washington DC in June, expect nights in New York City to be about the same, around 65°F, while days are slightly colder, around 80°F. Finish your sightseeing early on the 9th (Sun) so you can travel to Chicago.

Things to do in New York City

Parks Tours Neighborhoods

Side Trip

Brooklyn Botanic Garden
Highlights from your plan
Central Park ©
Central Park
Times Square ©
Times Square
Chelsea Market ©
Chelsea Market

4
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Your day-by-day itinerary now includes Museum of Science and Industry as well as Chicago Riverwalk. You'll discover tucked-away gems like The Magnificent Mile and Water Tower Place. Head to Chicago Premium Outlets and Lincoln Parkfor some retail therapy. You'll find plenty of places to visit near Chicago: Woodfield Mall (in Schaumburg) and Indiana Dunes State Park (in Chesterton). There's lots more to do: admire the masterpieces at The Art Institute of Chicago, make a trip to Buckingham Fountain, and browse the eclectic array of goods at Maxwell Street Market.

For photos, more things to do, maps, and other tourist information, read our Chicago day trip tool .

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. In June in Chicago, expect temperatures between 81°F during the day and 63°F at night. On the 14th (Fri), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Chicago

Shopping Neighborhoods Museums

Side Trips

Chicago Premium Outlets, Woodfield Mall, Indiana Dunes State Park
Highlights from your plan
Lincoln Park ©
Lincoln Park
The Magnificent Mile ©
The Magnificent Mile
Indiana Dunes State Park ©
Indiana Dunes State Park

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