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 New York Public Library. 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 Tenafly Nature Center (in Tenafly), Tobay Beach (in Massapequa) and Hartsdale Pet Cemetery (in Hartsdale). And it doesn't end there: see the interesting displays at Ground Zero Museum Workshop, contemplate the long history of Ellis Island, explore the world behind art at The Metropolitan Museum of Art, and go for a charming ride with a horse-drawn carriage tour.

To find where to stay, ratings, more things to do, and tourist information, read New York City trip builder website.

Manila, Philippines to New York City is an approximately 19.5-hour flight. The time zone difference moving from Philippine Standard Time to Eastern Standard Time is minus 13 hours. Traveling from Manila in May, expect New York City to be colder, temps between 24°C and 15°C. Wrap up your sightseeing on the 29th (Fri) to allow time to fly 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 Chicago Cultural Center. Explore Chicago's surroundings by going to John Deere Historic Site (in Grand Detour), Saint Joseph (Krasl Art Center & Silver Beach County Park) and Veterans Memorial Park (in Dixon). The adventure continues: kick back and relax at New Buffalo Public Beach, test your team's savvy at The Escape Game Chicago, get curious at Museum of Science and Industry, and learn more about the world around you at Field Museum.

To find more things to do, traveler tips, ratings, and other tourist information, use the Chicago online trip itinerary builder.

Getting from New York City to Chicago by flight takes about 4 hours. Other options: drive; or take a bus. The time zone difference moving from Eastern Standard Time (EST) to Central Standard Time (CST) is minus 1 hour. May in Chicago sees daily highs of 25°C and lows of 13°C at night. 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