60 days in New York City & Chicago Itinerary

60 days in New York City & Chicago Itinerary

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Route & dates

60 days in New York City & Chicago Itinerary

Start: Manila, Luzon
Fly:  20​h 15​min
1
New York City
— 28 nights
Bus + Fly:  4​h 45​min
2
Chicago
— 30 nights
Fly:  22​h 45​min
End: Manila, Luzon

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.
You'll enjoy a bit of beach vacationing at Fire Island National Seashore and Long Beach. Satisfy your inner culture vulture at 9/11 Memorial and American Museum of Natural History. Get out of town with these interesting New York City side-trips: Tobay Beach (in Massapequa), Tenafly Nature Center (in Tenafly) and Hartsdale Pet Cemetery (in Hartsdale). There's still lots to do: explore the world behind art at The Museum of Modern Art, wander the streets of Dumbo, settle in for a delightful tour with a horse-drawn carriage tour, and see the interesting displays at Ground Zero Museum Workshop.

Plan trip to New York City with our itinerary maker to find out where to go and what to do.

Manila, Philippines to New York City is an approximately 20.5-hour flight. You can also do a combination of flight and bus; or do a combination of flight and train. The time zone difference moving from Philippines Time to Eastern Standard Time is minus 13 hours. Traveling from Manila in May, things will get much colder in New York City: highs are around 24°C and lows about 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 Parks Historic Sites

Side Trips

Brooklyn, Hyde Park, Staten Island, Long Beach, Tobay Beach
Highlights from your plan
New York Public Library ©
New York Public Library
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.
Get outdoors at Lakefront Trail and Grand Mere State Park. Visit North Avenue Beach and Oak Street Beach for some beach relaxation. Explore Chicago's surroundings by going to Veterans Memorial Park (in Dixon), Saint Joseph (Krasl Art Center & Silver Beach County Park) and John Deere Historic Site (in Grand Detour). The adventure continues: stroll through Starved Rock State Park, explore the activities along Lake Michigan, get curious at Museum of Science and Industry, and have some family-friendly fun at The Escape Game Chicago.

For traveler tips, ratings, photos, and more tourist information, use the Chicago day trip planning website .

You can do a combination of bus and flight from New York City to Chicago in 5 hours. Other options are to fly; or drive. You'll gain 1 hour traveling from New York City to Chicago due to the time zone difference. May in Chicago sees daily highs of 25°C and lows of 13°C at night. You'll have a few hours on the 28th (Sun) to wrap things up before traveling home.

Things to do in Chicago

Parks Outdoors Beaches

Side Trips

South Bend, Pontiac, Lake Geneva, Saint Joseph, Kenosha
Highlights from your plan
The Magnificent Mile ©
The Magnificent Mile
Starved Rock State Park ©
Starved Rock State Park
Lakefront Trail ©
Lakefront Trail

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