23 days in New York City & Chicago Itinerary

23 days in New York City & Chicago Itinerary

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Route & dates

23 days in New York City & Chicago Itinerary

Start: Ulaanbaatar
Fly:  17​h 45​min
1
New York City
— 12 nights
bus + Fly:  4​h 45​min
2
Chicago
— 9 nights
Fly:  23​h 15​min
End: Ulaanbaatar

12
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 Point Lookout Beach and Joel L. Lefkowitz Park at West Meadow Beach. Change things up with these side-trips from New York City: Cupsogue Beach County Park (in Westhampton Beach), Goodale Farms (in Riverhead) and Lido Beach (in Lido Beach). Next up on the itinerary: take in the pleasant sights at Central Park, take in panoramic vistas at Empire State Building, enjoy the sand and surf at Ocean Grove Beach, and appreciate the history behind Statue of Liberty National Monument.

To find reviews, where to stay, other places to visit, and more tourist information, read New York City trip itinerary maker app .

Ulaanbaatar, Mongolia to New York City is an approximately 18-hour combination of flight and bus. You can also fly. Due to the time zone difference, you'll gain 13 hours traveling from Ulaanbaatar to New York City. Prepare for somewhat warmer weather when traveling from Ulaanbaatar in June: high temperatures in New York City hover around 31°C and lows are around 21°C. Wrap up your sightseeing on the 8th (Mon) to allow time to travel to Chicago.

Things to do in New York City

Parks Beaches Outdoors

Side Trips

Gilgo Beach, Cupsogue Beach County Park, Great Neck Steppingstone Park, Point Lookout Beach, Goodale Farms
Highlights from your plan
Central Park ©
Central Park
Times Square ©
Times Square
Fifth Avenue ©
Fifth Avenue

9
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Your itinerary includes some good beach time at Bender Park Waterfront and Silver Beach County Park. Venture out of the city with trips to Waukegan Municipal Beach (in Waukegan), Hawthorn Hollow - Nature Sanctuary and Arboretum (in Kenosha) and Racine (Matt's Produce & North Beach Park). There's still lots to do: enjoy the sand and surf at Rosewood Beach, indulge your taste buds at Whiskey Acres Distilling Co., stroll through Kathy Osterman Beach, and engage your brain at Museum of Science and Industry.

To find ratings, more things to do, photos, and tourist information, go to the Chicago trip itinerary app .

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. The time zone difference moving from Eastern Standard Time to Central Standard Time is minus 1 hour. Traveling from New York City in July, you can expect nighttime temperatures to be little chillier in Chicago, with lows of 22°C. On the 17th (Wed), you'll have the morning to explore before heading back home.

Things to do in Chicago

Parks Outdoors Beaches

Side Trips

Racine, Bender Park Waterfront, Whihala Beach, Hawthorn Hollow - Nature Sanctuary and Arboretum, Whiskey Acres Distilling Co.
Highlights from your plan
Whiskey Acres Distilling Co. ©
Whiskey Acres Distilling Co.
The Magnificent Mile ©
The Magnificent Mile
Whihala Beach ©
Whihala Beach

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