20 days in Washington DC, Chicago & New York State Itinerary

20 days in Washington DC, Chicago & New York State Itinerary

Created using Inspirock United States trip builder

This plan was created by another user.  Make it your plan

Route & dates

20 days in Washington DC, Chicago & New York State Itinerary

Start: Riyadh
+2
Fly + bus + subway:  15​h 30​min
1
Washington DC
— 3 nights
Fly:  3​h 45​min
2
Chicago
— 3 nights
Fly + bus:  4​h 45​min
3
Niagara Falls
— 4 nights
Drive:  3​h
4
Watkins Glen
— 1 night
Drive:  3​h 15​min
5
Kerhonkson
— 2 nights
Drive:  2​h
6
New York City
— 6 nights
Fly:  15​h
End: Riyadh

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.
Get outdoors at Antietam National Battlefield and Tidal Basin. You'll explore and learn at National Air and Space Museum and National Gallery of Art. Step out of Washington DC to go to Arlington and see Mount Vernon Trail, which is approximately 32 minutes away. The adventure continues: learn more about the world around you at Smithsonian National Museum of Natural History, explore the world behind art at National Portrait Gallery, and pause for some photo ops at Vietnam Veterans Memorial.

For maps, more things to do, ratings, and other tourist information, you can read our Washington DC online trip itinerary maker .

Riyadh, Saudi Arabia to Washington DC is an approximately 15.5-hour combination of flight, bus, and subway. You can also fly; or do a combination of flight and train. Due to the time zone difference, you'll gain 8 hours traveling from Riyadh to Washington DC. Traveling from Riyadh in November, expect nights in Washington DC to be much colder, around 6°C, while days are little chillier, around 17°C. Finish your sightseeing early on the 5th (Tue) so you can travel to Chicago.

Things to do in Washington DC

Parks Museums Nature

Side Trips

Antietam National Battlefield, Mount Vernon Trail
Highlights from your plan
Antietam National Battlefield ©
Antietam National Battlefield
National Air and Space Museum ©
National Air and Space Museum
National Gallery of Art ©
National Gallery of Art

3
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Get in touch with nature at Swallow Cliff Stairs and Lakefront Trail. Visit Ernest Hemingway Birthplace and Millennium Park for their historical value. Step out of Chicago with an excursion to Little Red Schoolhouse in Willow Springs--about 34 minutes away. The adventure continues: admire the masterpieces at The Art Institute of Chicago, get curious at Museum of Science and Industry, take in the spiritual surroundings of Fourth Presbyterian Church, and test your problem-solving skills at Team vs Time.

To find other places to visit, where to stay, and tourist information, use the Chicago travel route planning website .

Traveling by flight from Washington DC to Chicago takes 4 hours. Alternatively, you can do a combination of train and flight; or drive. The time zone difference when traveling from Washington DC to Chicago is minus 1 hour. Traveling from Washington DC in November, things will get slightly colder in Chicago: highs are around 11°C and lows about 1°C. Wrap up your sightseeing on the 8th (Fri) early enough to travel to Niagara Falls.

Things to do in Chicago

Parks Outdoors Trails

Side Trips

Ernest Hemingway Birthplace, Swallow Cliff Stairs, Little Red Schoolhouse
Highlights from your plan
Little Red Schoolhouse ©
Little Red Schoolhouse
The Art Institute of Chicago ©
The Art Institute of Chicago
Museum of Science and Industry ©
Museum of Science and Industry

4
nights
Niagara Falls

Niagara Falls ©
The city of Niagara Falls houses the U.S.
Visiting Cave of the Winds and Niagara Wine Trail USA will get you outdoors. Our Lady of Victory Basilica and Oakwood Cemetery Heritage Foundation will appeal to history buffs. There's still lots to do: take in the dramatic scenery at Niagara Falls, pause for some serene contemplation at St. Mary of the Cataract R. C. Parish, take in the pleasant sights at Goat Island, and immerse yourself in nature at Devil's Hole State Park.

To see other places to visit and tourist information, read our Niagara Falls trip itinerary builder website .

You can do a combination of flight and bus from Chicago to Niagara Falls in 5 hours. Other options are to do a combination of flight and train; or drive. Due to the time zone difference, you'll lose 1 hour traveling from Chicago to Niagara Falls. In November in Niagara Falls, expect temperatures between 10°C during the day and 0°C at night. Finish your sightseeing early on the 12th (Tue) to allow enough time to drive to Watkins Glen.

Things to do in Niagara Falls

Parks Nature Outdoors

Side Trip

Our Lady of Victory Basilica
Highlights from your plan
Cave of the Winds ©
Cave of the Winds
Niagara Falls ©
Niagara Falls
Devil's Hole State Park ©
Devil's Hole State Park

1
night
Watkins Glen

Watkins Glen ©
Watkins Glen is a village in Schuyler County, New York, United States. Start off your visit on the 13th (Wed): delve into the lush surroundings at Henry A. Smith Woods, learn about winemaking at Silver Springs Winery L.L.C., then admire the majestic nature at Watkins Glen State Park, and finally pause for some serene contemplation at Garrett Memorial Chapel.

To see reviews, ratings, and tourist information, go to the Watkins Glen trip website .

Drive from Niagara Falls to Watkins Glen in 3 hours. Alternatively, you can do a combination of train and bus; or take a bus. In November, daytime highs in Watkins Glen are 11°C, while nighttime lows are -1°C. Cap off your sightseeing on the 13th (Wed) early enough to travel to Kerhonkson.

Things to do in Watkins Glen

Nature Parks Outdoors

Side Trips

Silver Springs Winery L.L.C., Garrett Memorial Chapel, Henry A. Smith Woods
Highlights from your plan
Watkins Glen State Park ©
Watkins Glen State Park
Silver Springs Winery L.L.C. ©
Silver Springs Winery L.L.C.

2
nights
Kerhonkson

Kerhonkson ©
Kerhonkson is a hamlet (and census-designated place) in Ulster County, New York, United States. On the 14th (Thu), take your sightseeing to a higher altitude at Catskill Park, immerse yourself in nature at Minnewaska State Park Preserve, and then pause for some serene contemplation at Cragsmoor Stone Church. On your second day here, take in the awesome beauty at Schunnemunk State Park, then take your sightseeing to a higher altitude at Anthony's Nose, and then admire the masterpieces at Magazzino Italian Art.

Use Inspirock's suggestions to plan your Kerhonkson trip and find the best activities and attractions for your vacation.

Getting from Watkins Glen to Kerhonkson by car takes about 3.5 hours. In November, daytime highs in Kerhonkson are 12°C, while nighttime lows are 0°C. Wrap up your sightseeing on the 15th (Fri) early enough to travel to New York City.

Things to do in Kerhonkson

Parks Nature Wildlife

Side Trips

Schunnemunk State Park, Cragsmoor Stone Church, Anthony's Nose, Magazzino Italian Art, Catskill Park
Highlights from your plan
Minnewaska State Park Preserve ©
Minnewaska State Park Preserve
Anthony's Nose ©
Anthony's Nose
Magazzino Italian Art ©
Magazzino Italian Art

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.
Deepen your sense of the past at sights like 9/11 Memorial and Ellis Island. Take a break from the city and head to East River Waterfront Esplanade and Hudson River Greenway. There's still lots to do: go for a walk through Central Park, pause for some serene contemplation at St. Patrick's Cathedral, make a trip to The Metropolitan Museum of Art, and get to know the fascinating history of Central Park's Literary Walk.

For more things to do, traveler tips, maps, and more tourist information, refer to the New York City itinerary builder site .

Drive from Kerhonkson to New York City in 2.5 hours. Prepare for somewhat warmer weather when traveling from Kerhonkson in November: high temperatures in New York City hover around 16°C and lows are around 7°C. Finish up your sightseeing early on the 21st (Thu) so you can travel back home.

Things to do in New York City

Museums Parks Outdoors
Highlights from your plan
Central Park ©
Central Park
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art
American Museum of Natural History ©
American Museum of Natural History

Similar Plans

21 days in Washington DC BY A USER FROM BRAZIL September, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife, slow & easy, hidden gems PREFERENCES: September, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Hidden gems PACE: Slow & easy 23 days in United States BY A USER FROM ITALY August, kids, culture, relaxing, beaches, museums, shopping, popular & hidden gems PREFERENCES: August, kids, culture, relaxing, beaches, museums, shopping ATTRACTION STYLE: Popular & hidden gems PACE: Medium 21 days in Washington DC BY A USER FROM BRAZIL September, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife, slow & easy, popular sights PREFERENCES: September, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Slow & easy 21 days in United States BY A USER FROM INDIA June, culture, outdoors, relaxing, romantic, beaches, shopping, popular sights PREFERENCES: June, culture, outdoors, relaxing, romantic, beaches, shopping ATTRACTION STYLE: Popular sights PACE: Medium 38 days in United States BY A USER FROM PAKISTAN June, kids, culture, relaxing, beaches, shopping, slow & easy, popular & hidden gems PREFERENCES: June, kids, culture, relaxing, beaches, shopping ATTRACTION STYLE: Popular & hidden gems PACE: Slow & easy 25 days in United States BY A USER FROM AUSTRALIA January, culture, relaxing, romantic, beaches, museums, shopping, wildlife, popular & hidden gems PREFERENCES: January, culture, relaxing, romantic, beaches, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 41 days in United States BY A USER FROM INDIA June, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, fast-paced, popular & hidden gems PREFERENCES: June, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Fast-paced 32 days in United States BY A USER FROM AUSTRALIA June, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, fast-paced, popular & hidden gems PREFERENCES: June, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Fast-paced 38 days in United States BY A USER FROM PAKISTAN June, kids, culture, relaxing, beaches, shopping, slow & easy, popular sights PREFERENCES: June, kids, culture, relaxing, beaches, shopping ATTRACTION STYLE: Popular sights PACE: Slow & easy 22 days in Chicago BY A USER FROM MONGOLIA June, culture, outdoors, romantic, historic sites, museums, shopping, popular sights PREFERENCES: June, culture, outdoors, romantic, historic sites, museums, shopping ATTRACTION STYLE: Popular sights PACE: Medium
View more plans