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
Fly
2
Chicago
— 8 nights
Fly
3
Seattle
— 8 nights
Fly

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11
nights
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 The Met Cloisters. 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 still lots to do: browse the exhibits of The Metropolitan Museum of Art, appreciate the history behind 9/11 Memorial, go for a walk through Central Park, and admire the masterpieces at Frick Collection.

To see more things to do and other tourist information, read New York City trip builder.

The Route module shows you 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

Museums · Parks · Historic Sites · Neighborhoods

Side Trips

8
nights
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 The Magnificent Mile. Appreciate the collections at The Art Institute of Chicago and Field Museum. Explore the numerous day-trip ideas around Chicago: Westclox Museum (in Peru), Prairie Wolf Slough (in Highland Park) and Utica (Starved Rock State Park & August Hill Winery & Illinois Sparkling Co. Tasting Room). There's still lots to do: indulge in some culinary diversions at a local gastronomic tour, admire the local landmark of Buckingham Fountain, get curious at Museum of Science and Industry, and trek along Little Red Schoolhouse.

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

8
nights
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 Museum of Pop Culture. Explore hidden gems such as Snoqualmie Falls and Seattle Public Library. You'll find plenty of places to visit near Seattle: Belfair (Theler Wetlands Belfair Nature Preserve & Belfair State Park), Twin Falls (in North Bend) and Museum of Glass (in Tacoma). Dedicate the 13th (Sun) to wine at some of the top wineries in the area. The adventure continues: get a taste of the local shopping with Chihuly Garden and Glass, admire the striking features of Sky View Observatory, take in panoramic vistas at Space Needle, and take a stroll through Pike Place Market.

To see reviews, ratings, photos, and more tourist information, refer to the Seattle sightseeing planner.

Traveling by flight from Chicago to Seattle takes 7 hours. Alternatively, you can drive; or take a train. Traveling from Chicago to Seattle, you'll gain 2 hours due to the time zone difference. Expect little chillier temperatures when traveling from Chicago in June; daily highs in Seattle reach 74°F and lows reach 57°F. Wrap up your sightseeing by early afternoon on the 20th (Sun) to allow time for travel back home.

Things to do in Seattle

Tours · Parks · Wineries · Nature

Side Trips