Beat the Winter Blues at Pinstripes Chicago

Once winter arrives, the idea of leaving your apartment becomes very unappealing. The thought of walking through the snow while wind slaps you sharply across the face is hard to stomach. If you actually make it out the door to go out to dinner, the chance of going somewhere afterwards is slim. The carefree bar hopping days of summer are over (at least for the next few months). However, if you want to go out to dinner and have a little fun afterwards, Pinstripes offers a solution. Located in Streeterville at East Illinois and Peshtigo, this expansive space serves Italian-American comfort food alongside bowling and bocce ball — all in one building.

Mozzarella Marinara

Ordering the mozzarella marinara is a hearty way to begin the meal. Served in a hot iron skillet, the breaded and deep fried mozzarella balls sit atop a creamy mixture of housemade marina and lightly charred mozzarella. It warms you from the inside out!

Fig proscuitto flatbread from Pinstripes Chicago.

Photo courtesy of Pinstripes

Prosciutto Fig Flatbread

A winter favorite, the succulent figs on the prosciutto fig flatbread are marinated in balsamic and pair well with the pungent flavors of gorgonzola that are then in turn balanced by the sweetness of mascarpone. The prosciutto adds a salty crunch. This mouthwatering appetizer is meant for sharing.

A hearty piece of homemade lasagna from Pinstripes Chicago.

Photo courtesy of Pinstripes


Served in a cast iron baking dish, the decadent piece of thick-cut lasagna is made from fresh pasta that is sandwiched between layers of meat ragu and a sultry blend of ricotta, mozzarella and Parmesan cheeses. The pool of housemade marinara sauce that surrounds it complements the flavors of the already mouthwatering dish. It will leave a smile on your face because it tastes like home (assuming someone in your household had a killer lasagna recipe and knew how to execute it). Wash it down with a glass of Parcel 41 Pinot Noir.

Homemade marshmallows for s'mores at Pinstripes Chicago.

Photo courtesy of Pinstripes

Homemade S’mores

Homemade marshmallows are having a moment and these deserve a round of applause. The fluffy vanilla marshmallows are placed between two graham crackers and served with warm chocolate sauce on the side. No campfire required.

Warm brownie with gelato at Pinstripes Chicago on the Chicago Chic by Leah Nolan.

Photo courtesy of Pinstripes

Warm Brownie & Gelato

They had me at triple chocolate and housemade gelato. Three fudgy brownies are served with creamy homemade vanilla gelato and a generous dollop of whipped cream on the side. This dessert was simple, straightforward and a total knockout.

Private bowling at Pinstripes.

After dinner, pop by the bocce ball court or bowling alley. Both games must be reserved beforehand and if it is available, I recommend booking the private section of the bowling alley. The space boasts two lanes, leather couches and two tables. It feels like you are hanging out at a friend’s house, except you have a personal waiter, a vast food and wine selection and are wearing funny shoes that don’t belong to you. This environment is conducive to winter and has something for all ages.

435 E Illinois St, Chicago, IL 60611 | Pinstripes | (312) 527-3010


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