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

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

Created using Inspirock United States tour planner

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New York City
— 14 nights
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Washington DC
— 12 nights
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Chicago
— 9 nights
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New York City

— 14 nights

Big Apple

Writer Pearl Buck once called New York City “a place apart,” and this giant urban center remains unlike any other in the world.
New York Public Library and Frick Collection are good opportunities to explore the local culture. You'll explore and learn at Franklin D. Roosevelt Presidential Library and Museum and The Museum of Modern Art (MoMA). Explore the numerous day-trip ideas around New York City: Stone Church (in Dover Plains), Kismet Beach (in Kismet) and Home of Franklin D. Roosevelt (in Hyde Park). The adventure continues: admire the masterpieces at Philadelphia Museum of Art, take a stroll through Greenwich Village, examine the collection at Tenement Museum, and take an in-depth tour of Eastern State Penitentiary.

To find reviews, more things to do, where to stay, and tourist information, use the New York City trip itinerary planning tool.

Bogota, Colombia to New York City is an approximately 8.5-hour flight. Traveling from Bogota in June, expect New York City to be a bit warmer, temps between 31°C and 21°C. Wrap up your sightseeing by early afternoon on the 14th (Wed) to allow time for the flight to Washington DC.

Things to do in New York City

Museums · Parks · Outdoors · Beaches

Side Trips

Find places to stay Jun 30 — Jul 14:

Washington DC

— 12 nights
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.
Satisfy your inner culture vulture at Smithsonian National Museum of Natural History and National Gallery of Art. Museum-lovers will get to explore United States Holocaust Memorial Museum and U.S. Naval Academy. Explore Washington DC's surroundings by going to Gettysburg (Gettysburg National Military Park Museum & Visitor Center, Gettysburg National Military Park, &more), Mister Ed's Elephant Museum (in Orrtanna) and Baltimore (American Visionary Art Museum, Historic Ships in Baltimore, &more). Spend the 21st (Wed) exploring nature at Harpers Ferry National Historical Park. There's still lots to do: visit Georgetown, admire the striking features of George Washington's Mount Vernon, explore the world behind art at National Portrait Gallery, and take an in-depth tour of Smithsonian American Art Museum.

For reviews, photos, ratings, and tourist information, read our Washington DC trip website.

Getting from New York City to Washington DC by flight takes about 3 hours. Other options: take a train; or drive. In July, daily temperatures in Washington DC can reach 37°C, while at night they dip to 26°C. Cap off your sightseeing on the 26th (Mon) early enough to catch the flight to Chicago.

Things to do in Washington DC

Museums · Historic Sites · Parks · Neighborhoods

Side Trips

Find places to stay Jul 14 — 26:

Chicago

— 9 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Your cultural itinerary includes sights like The Art Institute of Chicago and Field Museum. You'll explore the less-touristy side of things at Chicago Riverwalk and Milwaukee Art Museum. Get out of town with these interesting Chicago side-trips: Ogden Dunes Beach (in Portage), Milwaukee (Bradford Beach, Grohmann Museum, &more) and Whihala Beach (in Whiting). There's much more to do: get curious at Museum of Science and Industry, learn about all things military at Livingston County War Museum, browse the exhibits of Chicago Cultural Center, and tour the pleasant surroundings at Oak Street Beach.

For where to stay, other places to visit, ratings, and other tourist information, you can read our Chicago online day trip planner.

Fly from Washington DC to Chicago in 3.5 hours. Alternatively, you can drive; or take a train. Due to the time zone difference, you'll gain 1 hour traveling from Washington DC to Chicago. Prepare for slightly colder weather when traveling from Washington DC in July: high temperatures in Chicago hover around 33°C and lows are around 22°C. Wrap up your sightseeing by early afternoon on the 4th (Wed) to allow enough time to fly back home.

Things to do in Chicago

Museums · Parks · Outdoors · Beaches

Side Trips

Find places to stay Jul 26 — Aug 4: