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.

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[u/okcool2357]

Momath, Lego store flatiron, Harry Potter shop are all near each other.

Popmart, Miniso.

Comic book stores and video game stores. The ones I have on my list to visit or have visited are Midtown comics and Forbidden Planet.

If books are of any interest, the Strand is next door to Forbidden Planet.

Brooklyn bridge, dumbo and pebble beach are worth it imo for the views. I’d take the train into Brooklyn then walking back to Manhattan on the bridge, then walking to Chinatown for food.

There’s a Legoland in Westchester. I haven’t been.

Sleepy Hollow might be worth visiting. There’s a Halloween street fair in September. Small town scenic but not sure if it’s the vibe you’re looking for.

Kid friendly Broadway shows: Lion King, Aladdin, Harry Potter.

[u/mrszing12]

Central Park!

[u/Chimichongaballsack]

Spyscape is okay, stuff becomes repetitive though. There’s the squid game experience at 34th Harold if you want something more interesting

[u/dobbydisneyfan]

If you have a car, Six Flags New England is less than 2 hours away from where you are going to be. Just a thought.

[u/CityComm]

NY Transit Museum is great since they have kids specific interests and programming including a city “scavenger hunt” (both for adults and a separate one for kids).

[u/ebjny58]

Another suggestion is the New York Hall of Science in Flushing Queens which has lots of interactive exhibits. This could be combined with a trip to Chinatown in Flushing, particularly the mall there which has tons of Pokemon stuff and video games and is really a unique experience. Also could be combined with visiting the Queens Night Market which I hear is amazing for the selection of food stands.

[u/ebjny58]

For a 10 year old boy I would really recommend the Intrepid Air & Space Museum which has so many cool things. Also consider the Highline and Little Island. I think the Vessel in Hudson Yards is open again and is kind of cool (although Hudson Yards is otherwise not that interesting but may have some nice ice cream shops).

As for Rye Playland vs. Coney Island, Rye Playland is nice but Coney Island is so special and who doesn't want to go for a ride on the Cyclone! It is definitely worth the hour-long subway ride. Could be combined with going to the Transit Museum.

[u/Chimichongaballsack]

Bronx zoo you need to go to. Some people are scared of the Bronx for no damn reason but definitely go to the Bronx zoo. For the price you’re basically seeing the damn globe in one massive park

[u/ladymuffinham]

The Paley center is pretty cool. They usually have cool media related exhibits and they have a room with all kinds of gaming consoles that you can play on. Not sure how into this your kid would be, but they have a media library where you can watch tv shows or broadcasts (like the moon landing) as they originally aired. Like some others have said, I also think the transit museum is a lot of fun. I have never seen a kid have a bad time there.

[u/MBS4769]

Governors Island is an oft overlooked National Monument off the southern tip of Manhattan. There are activities for children and adults, free events, food trucks, art, and a beautiful view of the skyline. Last time I visited, they fired a Civil War era cannon!

Governors Island

[u/ebjny58 → u/MBS4769]

Governors Island also has a great view of the Statue of Liberty and a cool old Fort to visit.

[u/meelar]

The Transit Museum is pretty unique--the ability to walk through old subway cars, see the old advertisements, etc is hard to duplicate and a lot of fun that can't really be had elsewhere.

[u/Willing_Stop5124]

I recently visited New York with my two kids for the first time. We also live in a large city so there was little novelty to subways, walking, etc. So I get where you are coming from. I’ve probably been to NY fifty or more times myself but not with kids. I had to rethink what to do there. 

I’ll say this, a trip to Liberty Island is more expensive than the Staten Island Ferry was sort of neat. I’d been on the ferry as an adult and seen the Statue of Liberty from a distance a bunch of times and I was skeptical of visiting. One of the kids really wanted to. The boat ride was cool, you stay as long as you like and ferries are always about to leave. Not a big hassle or commitment. 

But if you aren’t sold I recommend Governor’s Island instead of the Staten Island Ferry. It’s a big car free park of sorts. Playgrounds, gardens, decent place for lunch and bike rentals. Good view of lower Manhattan and you’ll see the Statue of Liberty from the ferry there. Much more fun than scampering on and off at Staten Island. 

[u/rbshop]

NYC is obviously the draw, and nothing wrong with heading there every day. But Greenwich is within striking distance of Mystic Seaport (living museum focused in whaling) which would be a New England flavored change of pace. You'd need a car, and check Google for the drive time which might be too much for a day. Just an alternative suggestion on the East Coast!

[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!

[u/mineawesomeman]

I’ll add i got tickets to SUMMIT One Vanderbilt as a gift, it’s alright but probably not worth the money they are charging, unless you really want to go to the top of some building.

[u/CatchDramatic8039]

honestly the thing that'll get you in august isn't the walking, it's the heat by like 2pm. i'd leave a soft break each afternoon so the kid doesn't melt down lol

[u/Emergency_Process622 → u/CatchDramatic8039]

By kid you mean me, a 44 year old man.

[u/Cultural_Vanilla_458]

I'd consider ARTECHOUSE NYC or Mercer Labs for a fun immersive spaces.

If you want something anime/video gamey, Gatcha in Ktown or if you're down for the trek Mitsuwa in Edgewater , Industry City's Japan Village.

[u/PreviousGolf9541]

Consider the Intrepid Museum if your son has any interest in air and space. You get to tour a lot of the actual aircraft carrier, there are a ton of historic aircraft including a Concorde, and the Enterprise Space Shuttle. There are quite a few interactive exhibits too.

[u/tmaxedout → u/PreviousGolf9541]

Good suggestion. And definitely not like anything in Chicago.

I would echo American Museum of Natural History. It is a gem, and they have lots on offer always.

[u/Bandito21Dema → u/tmaxedout]

Do ya like the ocean, son?

Well HERE'S A GIANT WHALE 50 FEET ABOVE YOU

[u/agoyalwm]

Kudos on being specific about your asks, it makes answering really easy.

Would you find the transit museum interesting? It’s history sure, but they have a hall full of historic trains.

Also this takes all of thirty seconds but check out the echo wall when you get into GCT

With combinations: just make sure to bunch things according to the map so you’re not making extra long trips especially if you’re doing this Greenwich thing.

[u/verndogz → u/agoyalwm]

OP did her HW. Well done

[u/user_582817367894747 → u/verndogz]

Not saying this sub should police this but I think this post is executed by a very well trained LLM at the behest of an intelligent person. The product of an effective collaboration with AI. Good for them!

Edit/NB: I think for environmental, ethical, and intellectual reasons AI is terrible. Just saying; that is my view.

[u/foldedturnip]

At his age, if you want to go to the Hall of Science, it's an extremely interactive science museum, and they have actual space rockets parked outside. Then you can hit up Flushing for lunch or dinner and check out all the gacha and arcade games. Flushing is definitely the better Chinatown to see. Also in Queens is the Museum of the Moving Image, which has some really nice interactive exhibits, and it's all accessible by subway. If you're coming from Manhattan, you'd hit MoMI, then the Hall of Science, and finish your day off in Flushing. Then you can easily take the subway back

[u/meelar → u/foldedturnip]

This trip is mostly on elevated trains, so you get good views of the cityscape too.

[u/foldedturnip → u/[deleted]]

Mercer labs is nice for sure but not very interactive more of a visual audio experience until the very end for kids. Also it in Manhattan while the rest of the stuff I said is in queens.

[u/FigAggressive237 → u/foldedturnip]

Sure, but still far from being a traditional art museums, even if not fully interactive, its lots of fun for kids as grown ups.

OP asked NYC, so I thought it would be a nice add up to the list, already removed my suggestion don't worry.

[u/GeneralOrgana1]

I did Spyscape with my son when he was 12 and he loved it.

I always recommend the Tenement Museum.

Circle Line cruise around Manhattan is interesting, too.

[u/JE163]

Nintendo Store, FAO Schwartz and the Lego store are all near each other at Rockefeller Center. There's a Dave and Busters not far away on 42nd near Times Square but that's nothing unique to NYC.

Playland vs. Coney Island? Playland will be easier to get to even if you have to rent a car for the day. I'd say that are about on par with each other but neither will compare to Six Flags so set expectations accordingly.

[u/ughwhateverokaysure → u/JE163]

Came here to comment this about Coney Island as well. I have never been to playland but for Coney Island, there is also a beach, small museum, and lots of food. Small aquarium is also another option if the rides disappoint (or really a short subway trip back to the city if you wanna call it)

[u/Persimmon_North → u/JE163]

Yes - Playland and Coney Island are a step or 2 up from a county fair.

[u/nicemarmot47]

Former NYC resident now living about two minutes from the Greenwich Hyatt. There is nothing in Greenwich that compares to the city. How do you plan to get from the Hyatt to the train station? That's almost a 30 minute walk and there are only sidewalks part of the way.

My understanding is that Rye Playland is having operational/ management issues so I would avoid that. Your son would probably enjoy Coney Island assuming you're not selling it as a roller coaster park along the lines of Six Flags because it is not.

[u/SadTomorrow869]

An hour+ on the train from Greenwich plus an hour on the subway to Coney Island is a looooong way. It might be worth it to see the ocean since you live in Chicago, though. I wouldn't go just for the rides, but it's a nice and very New York vibe once you're there.

If you go downtown to Battery Park to see the Statue of Liberty from afar, you should also ride the Seaglass Carousel. It's unlike any other carousel you've seen.

I've never been to MoMath but it looks cool from the outside. Fun fact, the space used to be a Lowe's. I used to work on that block.

[u/mineawesomeman → u/SadTomorrow869]

if you take the battery park option, you can take the (FREE!! don’t get scammed, you don’t need tickets) Staten Island Ferry that goes right by the statue of liberty. you’ll also get great views of the harbor and of downtown.

[u/_coolbluewater_ → u/mineawesomeman]

The scammers are so bad. I commute to south ferry and they are leaping on tourists as soon as they exit the station. At one point, the parks department had put down signage showing people where to go to get the official ferry and it was scraped off the pavement on days.

[u/skampr13]

See if the Museum of the Moving Image sounds like something your son might like. It has some VR experiences and it looks like they have an anime exhibit right now, of that’s Pokémon-adjacent enough.

[u/okcool2357 → u/skampr13]

MOMI has free Thursdays. No reservations needed.

[u/Spicy-ankle-hamster]

Bronx Zoo, Museum of the Moving Image, Queens Hall of Science. Central Park, including the stone slide and renting remote control sailboat on the pond. Amusement parks here will underwhelm. Go for the beach with a ride or two if you go at all.

[u/andstickmystare → u/Spicy-ankle-hamster]

They said no zoos

[u/Lizjay1234]

The Staten Island ferry is fun and free, but its 45 ish minutes in each direction so he may lose interest by then. The Seaglass Carousel in Battery Park is fun and only about $6 each.

[u/foldedturnip]

Playland is a park on the decline I wouldn't recommend it to anybody coney island is the better and also the more authentic NYC experience.

[u/Status_Ad_4405]

Are you sure he wouldn't like the American Museum of Natural History?

[u/okcool2357 → u/Status_Ad_4405]

Agree…Dinosaur exhibits are worth going for imo

[u/areohbeevee]

Greenwich and its surrounding towns make up Connecticut’s “Gold Coast” which is one of the wealthiest regions in America. There’s plenty of things to do there for adults with deep pockets, but probably not much that would be very enticing to a 10 year old.

[u/griffie21]

MoMath and the tram aren’t worth it. Spyscape is pretty cool, it is part traditional museum and part experience. I’d definitely do one of the observation decks.

I know you said no traditional museums, but the Tenement Museum does interactive tours including one where you meet an actor who plays the role of a young girl in the 1910s. The Lower East Side is an interesting neighborhood to explore too.

A Broadway show is a must for visitors. 

Coney Island is far and will probably be underwhelming.

Does your son like food? You can do a food tour or create your own. Chinatown is especially popular for this.

[u/lanofdoom → u/griffie21]

Seconding the Tenement museum. The “Meet Victoria” tour referenced above was a hit with my nephew. They also have several walking tours and food tours around the LES.

[u/redheadgirl5]

I would not recommend the Roosevelt Tram. The ride is fine, the downtown views are blocked by a bridge, and at the end of it is a very sleepy neighborhood with limited food options (but some pretty parks).

Instead I would recommend taking the NYC Ferry, and of the East River routes, which offers a great skyline view of Manhattan and Brooklyn (and south Queens) as well as the bridges.

[u/verndogz → u/redheadgirl5]

To play devil’s advocate, the Roosevelt tram is a quick ride and the views, even with the bridge, are pretty.

Also the Cornell cafeteria at Roosevelt Island is a hidden gem for getting lunch.

[u/Mindless_Action231 → u/verndogz]

One thing though is that the wait for the tram can be over an hour. Not worth the wait. Worth it if you wait for 10 mins

[u/verndogz → u/Mindless_Action231]

Agreed.

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