15 days in New York City, Chicago & Montreal Itinerary

15 days in New York City, Chicago & Montreal Itinerary

Created using Inspirock trip itinerary maker

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New York City, United States
— 4 nights
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Chicago, United States
— 5 nights
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Montreal, Canada
— 5 nights
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New York City, United States

— 4 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.
Take a break from the city and head to Rockaway Beach and Brighton Beach. You'll explore the less-touristy side of things at Vanderbilt Mansion National Historic Site and Frick Collection. You'll find plenty of places to visit near New York City: Hyde Park (Home of Franklin D. Roosevelt & Train Station). There's still lots to do: see the interesting displays at Ground Zero Museum Workshop, explore the world behind art at The Museum of Modern Art (MoMA), pause for some serene contemplation at St. Paul's Chapel, and wander the streets of Greenwich Village.

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

Milan, Italy to New York City is an approximately 12-hour flight. Traveling from Milan to New York City, you'll gain 6 hours due to the time zone difference. Prepare for slightly colder weather when traveling from Milan in January: high temperatures in New York City hover around 5°C and lows are around -5°C. On the 1st (Mon), wrap the sightseeing up by early afternoon so you can fly to Chicago.

Things to do in New York City

Museums · Historic Sites · Parks · Beaches

Side Trips

Find places to stay Jan 28 — Feb 1:
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Chicago, United States

— 5 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Discover out-of-the-way places like Milwaukee Public Museum and Milwaukee Art Museum. Step out of the city life by going to New Buffalo Public Beach and Ohio Street Beach. Venture out of the city with trips to Illinois Beach State Park (in Zion), Pine Meadow Golf Club (in Mundelein) and North Beach Park (in Racine). There's lots more to do: stroll through North Avenue Beach, grab your bike and head to Lakefront Trail, enjoy the sand and surf at Kathy Osterman Beach, and view the masterpieces at Chicago Cultural Center.

To see ratings, more things to do, where to stay, and other tourist information, read Chicago trip planner.

You can fly from New York City to Chicago in 4 hours. Other options are to drive; or take a bus. Traveling from New York City to Chicago, you'll gain 1 hour due to the time zone difference. Prepare for slightly colder weather when traveling from New York City in February: high temperatures in Chicago hover around 2°C and lows are around -7°C. Wrap up your sightseeing on the 6th (Sat) to allow time to fly to Montreal.

Things to do in Chicago

Outdoors · Parks · Beaches · Museums

Side Trips

Find places to stay Feb 1 — 6:
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Montreal, Canada

— 5 nights

Quebec's Metropolis

Quebec's economic and cultural capital, Montreal serves as the province's major point of entry, known for its rich history and high standard of living.
Escape the urban bustle at Alaskan Adventure Dog Sledding and Aventures Neige. Get a sense of the local culture at Barbie Expo and Cathedral of Marie-Reine-du-Monde. Explore the numerous day-trip ideas around Montreal: Omega Park (in Montebello), Mont Blanc-Faustin (in Saint-Faustin-Lac-Carre) and Ancienne Prison de L'Orignal Old Jail (in L'Orignal). There's lots more to do: explore the landscape on two wheels at Old Port of Montreal, take an in-depth tour of Cite d'Histoire et d'Archeologie de Montreal, learn the secrets of beer at a beer tour and tasting, and stroll around Mount Royal Park.

To find ratings, where to stay, and other tourist information, you can read our Montreal trip planner.

You can fly from Chicago to Montreal in 5.5 hours. Other options are to drive; or do a combination of train and car. You'll lose 1 hour traveling from Chicago to Montreal due to the time zone difference. Traveling from Chicago in February, expect Montreal to be little chillier, temps between -4°C and -12°C. Finish your sightseeing early on the 11th (Thu) to allow enough time to fly back home.

Things to do in Montreal

Museums · Parks · Outdoors · Tours

Side Trips

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