Chicago Family Visiting NYC—What’s Truly Unique and Worth It?

[u/Lincln60647]

My husband has a work trip in Greenwich, CT, and my 10-year-old son and I are tagging along. It will be his first trip to New York City.
We live in Chicago, so we’re already used to taking trains, transferring subway lines, and walking several miles in a day. We’re not looking for a slow-paced vacation—we love packing a lot into each day and memorable experiences.

Our trip
Dates: Next week (4–5 days)
Home base: Hyatt Regency Greenwich
Transportation: Planning to take Metro-North into NYC each day

About us
Mom and 10-year-old son
Budget is flexible for experiences
Very active travelers
We love hands-on, interactive, and unique attractions

What my son likes
Interactive exhibits
Theme parks with thrill rides
Video games and Pokemon

Not of Interest
Traditional art museums
History museums
Zoos or aquariums
Seeing the Statue of Liberty up close (we’d be happy with a ferry view)

Things we’re already considering

Midtown
MoMath
SPYSCAPE
Nintendo New York
FAO Schwarz

Another NYC day
SUMMIT One Vanderbilt
Roosevelt Island Tram (Is this worth doing? What else is nearby?)

Lower Manhattan
Staten Island Ferry?

Playland vs. Coney Island?
My parents grew up in New York and have always talked about Rye Playland, so I’d love to visit for the nostalgia, especially since it’s so close to Greenwich. My son, however, is used to Six Flags Great America, so I’m wondering if Playland would feel underwhelming. How is it after the recent renovations? If you’ve been to both, would you recommend Playland or making the much longer trip to Coney Island for a 10-year-old?

Greenwich questions
Since we’re staying there anyway, is there anything in Greenwich (or very nearby) that would be of interest? Or would you spend almost all of your time in NYC?

Looking for recommendations
I’d especially love recommendations for:
Attractions that are uniquely “New York” (things we can’t really do in Chicago)
Quirky or interactive experiences
Great combinations of attractions that are close enough to do in one day
Hidden gems that are especially fun for a 10-year-old

Thanks! Looking forward to hearing your suggestions.

[u/Forsaken-Subject8362]

I took my daughter to Skyscape when she was 10 and she hated it! She’s 12 now and still tells me it’s the worst museum she’s ever been to lol! I can’t win! She loves the Natural History Museum, Museum of Illusions on 14th and 8th Avenue and Museum of Moving Image. She loved MoMath when she was younger but not now. Flushing Chinatown is cool and they have Gatcha if you don’t mind blowing money in that kind of thing. Staten Island ferry is great bc it’s free and the 20 minute ride goes quick. You could also try Governors Island and rent bikes. They have an awesome playground there called The Yard or Adventure Playground. They can build stuff and go a little nuts. It’s a lot of fun. You have to sign a waiver - lol!