Pinstripes: Sophisticated Meets Fun for Holiday Parties

Pinstripes: Sophisticated Meets Fun for Holiday Parties

I  dripped in from the November storm, my hair leaking onto my peacoat. “Someday” by Rob Thomas is playing. There are tiny spotlights that hang from the exposed ceiling.

There’s bocce and bowling to the left, the bar to the right, and a warm fireplace overlooking the Ogden Slip on the year-round patio straight back.

There are suede fringe booties and Italian loafers on the couple who just dashed in. They are informed that they are the first to arrive. Startled, they didn’t think this day would come.

High heel black wedges and a sandalwood scented girl group quickly follow in.

“Bocce while you wait?,” the hostess asked.

Pinstripes (435 E. Illinois St.) a 33,000 sq. upscale Chicago Italian restaurant and game center in River East with bistro, bowling, and bocce, invites you to change your frame of mind. The multi-purpose venue hosts thousands of events a year throughout the Chicago area at three other locations. But this year was Pinstripe’s first year in Chicago, according to Chicago Eater.

And tonight, while we are led into the dining area, a man is celebrating his birthday among several tables of his closest friends and family.

My friend and I grabbed the catty-corner table at the edge of Pinstripes. It was a quiet night and a cloudy one.

We were thankful for the warmth of the candles.

You Must Order the Bruschetta:

One of my favorite parts of any Italian meal is the bruschetta. In Florence, last year, I could have subsisted off of bruschetta alone.

The bruschetta at Pinstripes was flavorful, decadent with a spot of balsamic in the middle of oil, and fresh—the mozzarella was so fresh. It reminded me of Italy and of home.

Tomato-Mozzaralla Bruschetta at Pinstripes. Photo: Amanda Elliott


Skip the Cocktails, Complement with Wine:

Pinstripe’s offers a specialty cocktail list, wine by the bottle or glass, and a beer menu.

After sipping on specialty cocktails from other venues in Chicago like Yard House and Earls, I think that their secret sauce is in their in food.

The specialty cocktail I had was perfectly refreshing. The follow-up Chocolate Martini I had with dessert tasted straight out of a Hershey’s bottle. With only one stomach, I recommend wine to complement the Italian meal.

Margarita Italiano specialty cocktail at Pinstripes. Photo: Amanda Elliott

Housemade Pastas and Chef Specialties:

Beyond the soup and starters, Pinstripes offers five categories of food for dinner: pizza & flatbread, salads, sandwiches, housemade pastas, and chef specialties.

Our waiter, who by the way was informative and sweet, recommended the Chicken Parmesan, a classic and one of my favorites.

The food came out pipping hot and warmed our mouths and our bellies. It was delicious.

The all natural cage free chicken was tender; the red sauce surrounding the meal was a tad sweet. However, the pile of Cacio e Pepe pasta—a trendy , yet simple spaghetti dish—was elevated with a light sauce. I nearly finished the entire dish, savoring each hot, flavorful bite.

Chicken Parmesan at Pinstripes. Photo: Amanda Elliott
Chicken & Goat Cheese Housemade Pasta at Pinstripes. Photo: Amanda Elliott

The Chicken and Goat Cheese Housemade Pasta was equally good and flavorful. While alfredo-esque pasta dishes are usually saturated with sauce, the rosemary cream sauce drizzled over the fusilli was a welcomed change. The dish was complete with chunks of goat cheese and chicken.

S’Mores for Dessert:

Save room for dessert, especially the s’mores. It is messy, but it’s a game night and who doesn’t like to have a little fun with their food? Warning: don’t order on a date, but if you do, the nice waiter will bring your wet cloths to save you from sticky fingers.

The s’mores dish comes with chocolate fondue in the middle of the plate to dip a fresh—one of the freshest strawberries or to add extra chocolate to the gooey s’mores.

Housemade S’mores at Pinstripes. Photo: Amanda Elliott

I paired dessert with the ultimate dessert drink, the Chocolate Martini. By the end of the night, I felt just like a kid, happy with chocolate and bowling, but thankful for a place that borders sophisticated and fun.

Holiday Parties:

Pinstripes is so big and nicely sectioned that even though it has an open layout, it feels very secluded.

This is Pinstripes first winter at the River East Location. Pinstripes offers catering for office parties or  a refined and fun element to your holiday shenanigans with a private party at Pinstripes.



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