60 days in New York City & Chicago Itinerary

60 days in New York City & Chicago Itinerary

Created using Inspirock United States route builder

Make it your trip
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New York City
— 28 nights
Fly
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Chicago
— 30 nights
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New York City

— 28 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.
Museum-lovers will appreciate 9/11 Memorial and The Metropolitan Museum of Art. Popular historic sites such as St. Patrick's Cathedral and Home of Franklin D. Roosevelt are in your itinerary. Explore New York City's surroundings by going to Hartsdale Pet Cemetery (in Hartsdale), Tenafly Nature Center (in Tenafly) and Tobay Beach (in Massapequa). The adventure continues: learn more about the world around you at American Museum of Natural History, get some thrills on the water with a speed boat tour, see the interesting displays at Ground Zero Museum Workshop, and steep yourself in history at Franklin D. Roosevelt Presidential Library and Museum.

To find traveler tips, reviews, and more tourist information, you can read our New York City trip tool.

Manila, Philippines to New York City is an approximately 19.5-hour flight. The time zone difference moving from Philippine Standard Time (PST) to Eastern Standard Time (EST) is minus 13 hours. Traveling from Manila in May, expect New York City to be colder, temps between 24°C and 15°C. Cap off your sightseeing on the 29th (Fri) early enough to catch the flight to Chicago.

Things to do in New York City

Museums · Historic Sites · Parks · Outdoors

Side Trips

Chicago

— 30 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Step out of the city life by going to Lakefront Trail and Chicago River. Appreciate the collections at The Art Institute of Chicago and Field Museum. Explore Chicago's surroundings by going to John Deere Historic Site (in Grand Detour), Veterans Memorial Park (in Dixon) and Saint Joseph (Krasl Art Center & Silver Beach County Park). Next up on the itinerary: get curious at Museum of Science and Industry, test your team's savvy at The Escape Game Chicago, explore the activities along Lake Michigan, and wander the streets of The Magnificent Mile.

To see more things to do, other places to visit, and more tourist information, use the Chicago day trip planner.

Traveling by flight from New York City to Chicago takes 4 hours. Alternatively, you can drive; or take a bus. The time zone difference when traveling from New York City to Chicago is minus 1 hour. Expect a daytime high around 25°C in May, and nighttime lows around 13°C. On the 28th (Sun), you'll have the morning to explore before heading back home.

Things to do in Chicago

Parks · Outdoors · Beaches · Museums

Side Trips