Chicago, the “Second City”? Never

For the first time since our son was born, we took a real family vacation. For a brief respite from the city, our first stop was to visit our long-time friends in Fairfield County, Connecticut. These days were filled with “shows” put on by our six (in total) children, a trip to Kent Falls State Park, a Belgian chocolate shoppe, and an adults-only dinner at the best restaurant in Connecticut, right across the street from Yale. Then we headed into the Big Apple on the Metro North to make our kids wish of seeing the Statue of Liberty come true!

Every minute I was comparing New York with Chicago, and measuring how kid-friendly it really was. I would have to sum it up like this: New York is top-notch in its family friendliness, IF you know what you’re doing. Luckily, I have a friend and neighbor who used to live in New York and gave me a lot of good tips. And being a city parent already was the other piece to the puzzle.

First of all, like any good parent, you must actually make some plans in order to have a smooth vacation with kids. This means buying reserve tickets to the Statue of Liberty well in advance, to avoid the snaking 4-hour line through Battery Park. This also means planning some down time as well. You just can’t see every museum and architectural gem while dragging two kids along.

We did see a lot though, keeping the kids’ choices and each of our choices at the top of our list. Lady Liberty was all they really wanted – and they both loved it – and Gabriella loved the kids’ audio guide there and at Ellis Island too. We also treated them to their first-ever Ferris Wheel ride in the Times Square Toys ‘R Us. We even enjoyed another dinner without the kids at a coveted restaurant (thanks to a good family friend that lives in Manhattan and babysat for us!).

We then had a chance meeting of one of my favorite celebrity chefs, not at the restaurant, but on the street, saw the unique Highline Park (or train-track park as Nicholas says), the Chrysler Building ceiling mural, Grand Central Station, enjoyed dinner in Chinatown in spite of the growing mounds of evening trash on the sidewalk (Note: THANK YOU FOR OUR WELL-PLANNED ALLEYS, CHICAGO!), rode the Central Park Carousel and chalked the rocks in Sheep Meadow (yes, I packed sidewalk chalk and an inflatable ball), devoured Amy’s Bread, the Lobster Market and Jacques Torres’ chocolate shop at the Chelsea Food Market and even went grocery shopping at a bodega to breakfast/snack in our lovely suite with kitchenette at the Benjamin Hotel.

Some other memorable things, but let’s say, ummm, not necessarily highlights: Gabriella screaming and crying for the entire Ferry ride to Liberty Island. Fear of heights, and wind sensory issues. Need I say more? We immediately cancelled our plans to visit the observation deck of the Empire State Building. An emergency bathroom trip that resulted in my noise sensitive son Nicholas taking a face down duck-and-cover right on the floor of the most disgusting Starbucks bathroom I’ve ever seen, all because I flushed the toilet. But we did avoid pee in the stroller. And last, but certainly not least, our ill-fated trip to LaGuardia to head home. An accident and car fire closed the FDR expressway, with us sitting in our taxi on it. We had to pay the taxi (thanks for nothing) get ourselves, the kids and all our luggage across the three lanes of stopped traffic and people milling around, climb over an iron fence (thanks to the guy that helped David lift the luggage over), walk back across the FDR on a pedestrian footbridge, and find a new taxi on the street to take a different route to LaGuardia so we wouldn’t miss the last flight of the day. Note to self: I thought you knew NEVER to book the last flight of the day!

Taking an urban vacation when you already live in an urban environment is much less stressful, so we didn’t have the subway-mugging-walking down the street fear like I’m sure a lot of NYC visitors do. And I have to hand it to New York. How smart are they for planting gigantic suburban-chain restaurants right in the heart of Times Square? Don’t you know that Applebee’s has a good 2 hour wait for a table thanks to all those Ohio State fans! We city folks preferred to find out from the locals where to eat, other than a food timing-crisis trip to Q-Doba with our good friends. Thanks to Babbo, Joe’s Shanghai, Eataly, and the Chelsea Market, we LOVED dining in New York. And that’s coming from some serious Chicago foodies. (Tru, Trotter’s, Alinea, Everest, etc.)

I would definitely rate New York City high on my list of family-friendly vacations. Use your urban parent sense, your travel planning skills, and show your kids another great city. But don’t forget that you get to come home to the Second City, which will always be first in my book.

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