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

Route & dates

1
New York City
— 28 nights
2
Chicago
— 30 nights

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 The Museum of Modern Art (MoMA). Popular historic sites such as St. Patrick's Cathedral and Franklin D. Roosevelt Presidential Library and Museum 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). And it doesn't end there: get interesting insight from Tours, contemplate in the serene atmosphere at The Met Cloisters, steep yourself in history at Ellis Island, and learn more about the world around you at American Museum of Natural History.

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 °C and °C. Wrap up your sightseeing on the 29th (Fri) to allow time to travel to Chicago.

Things to do in New York City

Museums Parks Historic Sites

Side Trips

Brooklyn, Hyde Park, Southampton, Staten Island, Fire Island National Seashore
Find places to stay May 1 — 29:
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 Lake Michigan. Appreciate the collections at Museum of Science and Industry 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). There's lots more to do: learn more about the world around you at Field Museum, test your problem-solving skills at The Escape Game Chicago, tour the pleasant surroundings at New Buffalo Public Beach, and contemplate the waterfront views at Chicago River.

For maps, more things to do, ratings, and more tourist information, refer to the Chicago travel itinerary planner.

You can fly from New York City to Chicago in 5 hours. Alternatively, you can drive; or take a bus. Traveling from New York City to Chicago, you'll gain 1 hour due to the time zone difference. May in Chicago sees daily highs of °C and lows of °C at night. You will have some time to spend on the 28th (Sun) before leaving for home.

Things to do in Chicago

Parks Outdoors Beaches

Side Trips

South Bend, Pontiac, Lake Geneva, Saint Joseph, Kenosha
Find places to stay May 29 — Jun 28:
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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