For many years, it was well known that if you and your friends were in the know of where to find some of Chicago’s best treats, you’d know that Bar Siena in the West Loop of Chicago had some of the best take out desserts in the city. Just walk past the front door and down the side of the building and there lies a small take out window passing out an italian doughnut called a bomboloni. It became quite the evening destination. If you were in the West Loop for dinner, you were grabbing dessert here and eating it on the curb with the biggest smile on your face. With this great success and cult following, Bar Siena decided to spin off their bombolonis into a full fledged restaurant called BomboBar. One of the early locations of this was on Wells Street in Old Town.

BomboBar opened in the middle of this theater district just storefronts away from The Second City, Zanies Comedy Club, and right next to A Red Orchid Theater. While they were open for lunch and would catch an after school crowd of students from nearby schools, they were a hit with the evening crowd. BomboBar would bring in people who were coming out of a show or on their way to a bar to meet some friends.

The menu, of course, featured the now-famous bomboloni with four different types of sweet sauces, which came in their own individual squeeze bottles. It’s so rare these days that you get to provide your desserts with a localized injection of caramel, chocolate, or berry sauces. If you were looking for something savory and substantial, the menu also had sheet pan pizzas by the square and cheese burgers that were all made to order.

Sadly, as the city was locked down due to COVID, BomboBar in Old Town closed and did not re-open. Fans of the bomboloni can still get their fix at the side window at Bar Siena.