29 days in New York City, Chicago & Seattle Itinerary

29 days in New York City, Chicago & Seattle Itinerary

Created using Inspirock United States tour itinerary planner

Plan created by another user. Make it yours
1
New York City
— 11 nights
2
Chicago
— 8 nights
3
Seattle
— 8 nights

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11
nights
New York City

New York City ©

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.
You'll explore the less-touristy side of things at Greenwich Village and New York Public Library. Get in touch with nature at Speed Boats Tours and Tenafly Nature Center. Take a break from New York City with a short trip to Demarest Nature Center in Demarest, about 38 minutes away. There's lots more to do: browse the exhibits of The Metropolitan Museum of Art, appreciate the history behind 9/11 Memorial, admire the masterpieces at The Museum of Modern Art (MoMA), and wander the streets of Dumbo.

For maps, more things to do, ratings, and other tourist information, you can read our New York City online road trip planner.

Use the Route module to see travel options from your home to New York City. In May, daytime highs in New York City are 69°F, while nighttime lows are 55°F. Wrap up your sightseeing on the 4th (Fri) to allow time to travel to Chicago.

Things to do in New York City

Side Trips

Highlights from your trip
©
Specialty Museum
Ground Zero Museum Workshop
4.6
©
Specialty Museum
New York Public Library
4.7

8
nights
Chicago

Chicago ©

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
You'll explore the less-touristy side of things at Lakefront Trail and Food Tours. Appreciate the collections at The Art Institute of Chicago and Field Museum. Explore the numerous day-trip ideas around Chicago: Prairie Wolf Slough (in Highland Park), Utica (Starved Rock State Park & August Hill Winery & Illinois Sparkling Co. Tasting Room) and Westclox Museum (in Peru). There's still lots to do: take a stroll through The Magnificent Mile, admire the local landmark of Buckingham Fountain, get curious at Museum of Science and Industry, and grab your bike and head to Skokie Lagoons.

To find out how to plan a trip to Chicago, use our trip itinerary maker.

Fly from New York City to Chicago in 5 hours. Alternatively, you can drive; or take a bus. The time zone difference moving from Eastern Standard Time (EST) to Central Standard Time (CST) is minus 1 hour. In June, plan for daily highs up to 81°F, and evening lows to 63°F. Finish your sightseeing early on the 12th (Sat) so you can travel to Seattle.

Things to do in Chicago

Parks · Outdoors · Wildlife · Trails

Side Trips

Highlights from your trip
©
Must see
Lakefront Trail
4.8

8
nights
Seattle

Seattle ©

Emerald City

Nicknamed the "Emerald City" because of its abundant evergreen trees, Seattle is the cultural and business center of the Pacific Northwest, as well as a popular holiday destination.
Appreciate the collections at The Museum of Flight and Chihuly Garden and Glass. Explore hidden gems such as Snoqualmie Falls and Hiram M. Chittenden Locks. You'll find plenty of places to visit near Seattle: Twin Falls (in North Bend), Museum of Glass (in Tacoma) and Belfair (Theler Wetlands Belfair Nature Preserve & Belfair State Park). Dedicate the 13th (Sun) to wine at some of the top wineries in the area. Next up on the itinerary: examine the collection at Museum of Pop Culture, get interesting insight from Tours, admire the local landmark of Seattle Center, and take in panoramic vistas at Space Needle.

To find more things to do, photos, reviews, and tourist information, go to the Seattle trip itinerary planner.

You can fly from Chicago to Seattle in 7 hours. Other options are to drive; or take a train. You'll gain 2 hours traveling from Chicago to Seattle due to the time zone difference. Traveling from Chicago in June, expect Seattle to be slightly colder, temps between 74°F and 57°F. On the 20th (Sun), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Seattle

Tours · Parks · Wineries · Nature

Side Trips

Highlights from your trip
©
Must see
Snoqualmie Falls
4.7
©
Specialty Museum
The Museum of Flight
4.8
©
Specialty Museum
Museum of Pop Culture
4.1

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