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

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

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Route & dates

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

Start: Chicago
Fly + bus:  4​h 45​min
1
New York City
— 4 nights
Fly:  3​h 30​min
2
Washington DC
— 3 nights
Fly:  4​h
3
Chicago
— 1 night
Fly + taxi:  3​h
End: Dayton

4
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.
Get a sense of the local culture at The Met Cloisters and 9/11 Memorial. The Metropolitan Museum of Art and Ground Zero Museum Workshop will appeal to museum buffs. The adventure continues: get to know the fascinating history of Brooklyn Heights Promenade, wander the streets of Greenwich Village, examine the collection at New York Public Library, and stroll around Washington Square Park.

To see traveler tips, reviews, maps, and more tourist information, read our New York City tour itinerary builder .

Chicago to New York City is an approximately 5-hour combination of flight and bus. You can also fly; or drive. Traveling from Chicago to New York City, you'll lose 1 hour due to the time zone difference. In August, daily temperatures in New York City can reach 34°C, while at night they dip to 25°C. Wrap up your sightseeing by early afternoon on the 26th (Mon) to allow enough time to travel to Washington DC.

Things to do in New York City

Museums Neighborhoods Historic Sites

Side Trip

Brooklyn
Highlights from your plan
9/11 Memorial ©
9/11 Memorial
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art
The Met Cloisters ©
The Met Cloisters

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.
Eschew the tourist crowds and head to Basilica of the National Shrine of the Immaculate Conception and The Tomb of the Unknown Soldier. Get a sense of the local culture at National Gallery of Art and National Air and Space Museum. You'll find plenty of places to visit near Washington DC: Fredericksburg (Chatham Manor & Chatham Manor). And it doesn't end there: explore the world behind art at Smithsonian American Art Museum, get engrossed in the history at National Portrait Gallery, wander the streets of Georgetown, and pause for some photo ops at Vietnam Veterans Memorial.

Take the guesswork out of planning a Washington DC vacation by using our trip itinerary maker.

Traveling by flight from New York City to Washington DC takes 3.5 hours. Alternatively, you can take a train; or drive. August in Washington DC sees daily highs of 36°C and lows of 25°C at night. Finish your sightseeing early on the 29th (Thu) so you can travel to Chicago.

Things to do in Washington DC

Museums Historic Sites Neighborhoods

Side Trips

Fredericksburg, The Tomb of the Unknown Soldier
Highlights from your plan

1
night
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
For other places to visit, where to stay, and tourist information, go to the Chicago day trip planner .

You can fly from Washington DC to Chicago in 4 hours. Other options are to do a combination of train and flight; or drive. Due to the time zone difference, you'll gain 1 hour traveling from Washington DC to Chicago. In August, plan for daily highs up to 33°C, and evening lows to 22°C. Wrap up your sightseeing on the 30th (Fri) to allow time to travel back home.

Things to do in Chicago

Neighborhoods Museums Historic Sites
Highlights from your plan
The Loop ©
The Loop
The Art Institute of Chicago ©
The Art Institute of Chicago
Chicago Riverwalk ©
Chicago Riverwalk

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