60 days in New York City & Chicago Itinerary

60 days in New York City & Chicago Itinerary

Created using Inspirock United States route builder

Plan created by another user. Make it yours
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New York City
— 28 nights
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Chicago
— 30 nights

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28
nights
New York City

New York City ©
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 American Museum of Natural History. Popular historic sites such as St. Patrick's Cathedral and Ellis Island are in your itinerary. Explore New York City's surroundings by going to Tobay Beach (in Massapequa), Hartsdale Pet Cemetery (in Hartsdale) and Tenafly Nature Center (in Tenafly). And it doesn't end there: admire the masterpieces at The Museum of Modern Art (MoMA), get lost in a book at Franklin D. Roosevelt Presidential Library and Museum, examine the collection at New York Public Library, and race across the water with a speed boat tour.

To see where to stay, other places to visit, more things to do, and other tourist information, you can read our New York City trip maker.

Manila, Philippines to New York City is an approximately 20.5-hour flight. You'll gain 13 hours traveling from Manila to New York City due to the time zone difference. 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 travel to Chicago.

Things to do in New York City

Museums · Historic Sites · Parks

Side Trips

Brooklyn, Hyde Park, Staten Island, Southampton, Great Neck Steppingstone Park
Highlights from your plan
St. Patrick's Cathedral ©
St. Patrick's Cathedral
Home of Franklin D. Roosevelt
Home of Franklin D. Roosevelt

30
nights
Chicago

Chicago ©
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 Oak Street Beach. 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), Veterans Memorial Park (in Dixon) and Saint Joseph (Krasl Art Center & Silver Beach County Park). 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 5 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

Side Trips

Pontiac, South Bend, Kenosha, Saint Joseph, Lake Geneva
Highlights from your plan
Lakefront Trail ©
Lakefront Trail
Starved Rock State Park ©
Starved Rock State Park
The Art Institute of Chicago ©
The Art Institute of Chicago

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