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

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

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Route & dates

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

Start: New York City
bus + Fly:  4​h 45​min
1
Chicago
— 1 day
Fly:  4​h
2
Washington DC
— 2 nights
Fly:  3​h 15​min
3
New York City
— 6 nights
End: New York City

1
day
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Start off your visit on the 21st (Sun): explore the world behind art at The Art Institute of Chicago, then appreciate the extensive heritage of Millennium Park, and then make a trip to The Magnificent Mile.

To find where to stay, other places to visit, traveler tips, and more tourist information, refer to the Chicago driving holiday planning app .

New York City to Chicago is an approximately 5-hour combination of bus and flight. You can also fly; or drive. Due to the time zone difference, you'll gain 1 hour traveling from New York City to Chicago. Expect a bit cooler evenings in Chicago when traveling from New York City in April, with lows around 5°C. Finish up your sightseeing early on the 21st (Sun) so you can travel to Washington DC.

Things to do in Chicago

Neighborhoods Shopping Museums
Highlights from your plan
The Magnificent Mile ©
The Magnificent Mile
The Art Institute of Chicago ©
The Art Institute of Chicago
Millennium Park ©
Millennium Park

2
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.
Kick off your visit on the 22nd (Mon): explore the world behind art at National Gallery of Art, contemplate the long history of Old Town, then get to know the fascinating history of Tomb of the Unknowns, and finally admire the masterpieces at National Portrait Gallery. On the 23rd (Tue), you'll have a packed day of sightseeing: examine the collection at National Air and Space Museum, get to know the fascinating history of Capitol Hill, and then expand your understanding of the military at U.S. Naval Academy.

For ratings, more things to do, photos, and more tourist information, you can read our Washington DC trip maker tool .

Traveling by flight from Chicago to Washington DC takes 4 hours. Alternatively, you can 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. Expect somewhat warmer temperatures when traveling from Chicago in April; daily highs in Washington DC reach 23°C and lows reach 11°C. Cap off your sightseeing on the 23rd (Tue) early enough to travel to Ship Bottom.

Things to do in Washington DC

Museums Historic Sites Neighborhoods

Side Trips

Old Town, The Tomb of the Unknown Soldier, U.S. Naval Academy
Highlights from your plan
National Gallery of Art ©
National Gallery of Art
The Tomb of the Unknown Soldier ©
The Tomb of the Unknown Soldier
Old Town ©
Old Town

6
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.
Satisfy your inner culture vulture at Fifth Avenue and Alex Ferrone Gallery. Let the collections at 9/11 Memorial and American Museum of Natural History capture your imagination. Venture out of the city with trips to Ponquogue Beach (in Hampton Bays), Coffee Pot Cellars Tasting Room (in Cutchogue) and Patchogue (Fire Island National Seashore & Amazing Olive). There's much more to do: go for a walk through Times Square, browse the eclectic array of goods at Chelsea Market, enjoy the sand and surf at Ocean Grove Beach, and stroll through 8th Ave Jetty.

To find maps, traveler tips, more things to do, and tourist information, you can read our New York City trip maker app .

Traveling by flight from Washington DC to New York City takes 3.5 hours. Alternatively, you can take a train; or drive. Expect a bit cooler weather when traveling from Washington DC in April: highs in New York City hover around 19°C, while lows dip to 8°C. On the 29th (Mon), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in New York City

Beaches Parks Outdoors

Side Trips

Cutchogue, Patchogue, 8th Ave Jetty, Ponquogue Beach, Shinnecock East County Park
Highlights from your plan
Fire Island National Seashore ©
Fire Island National Seashore
9/11 Memorial ©
9/11 Memorial
American Museum of Natural History ©
American Museum of Natural History

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