Top 10 Restaurants In Old Town, Chicago

Class is the first thing that comes to mind when entering the Old Town Social. Not an in-your-face, fat-cat class but a subtle ambiance of being high-end without trying too hard. And that’s exactly what you get with the food and drinks as well. At The Old Town Social, it’s no wonder that the Old Fashioned is one of the best in the neighborhood. Old Town Social is a multipurpose restaurant. It’s a fantastic place for Sunday Funday Brunch, perfect for your dinner spot before the show, and an excellent choice for a cozy, personable gathering of friends.

If you’re new to the city, you might be tempted to hit the nearest Giordano’s for your taste of a Chicago deep dish pizza, but in Old Town, there’s only one deep dish king, Dinotto. The restaurant itself is cozy and continues in the Old Town tradition of being an ideal date destination. But the food at Dinotto takes precedence. After all, the deep dish is a staple in Chicago culture as much as apple pie is a staple in American culture. So for a real taste of authenticity, head to Dinotto.

Topo Gigio embodies everything that comes with excellent Italian food, comfort, hominess, and of course, romance. But during the warmer months in Old Town, Chicago, Topo Gigio becomes the best casual date spot in the neighborhood. With outdoor seating right on N Wells Street, you really get a sense of the neighborhood, the people laughing as they go to and from shows, the sweaty athletes heading to their favorite pub after a hard fought victory, and everyone else in between. This compounded with the exquisite Italian cuisine, such as their mouthwatering conchiglie alla sarda, a seashell pasta in a tomato-cream sauce with ground sausage, peas and pecorino cheese, make it impossible to go wrong with Topo Gigio.

In a city like Chicago that’s filled with history both big and small, the Twin Anchors finds itself in between, giving a glimpse in its own small way into the lives of historic, cultural giants like Frank Sinatra. Specializing in barbecue ribs since 1932, it’s no small wonder that many of their regulars claim this is the spot for ribs in the city. With its comfortable BBQ joint interior and incredibly personable wait staff, the Twin Anchors is a must. Apparently Sinatra thought so to, as he made sure to stop by every time he passed through the city.

In a neighborhood that revolves primarily around American-style food, it only makes sense that there has to be one restaurant that goes above and beyond. Welcome to Boka, where high-end American food is taken to the next level. With a fair price considering the quality of the dishes (i.e. their melt-in-your-mouth Rohan Duck with celery root, kumquat, and bitter greens) and an upscale atmosphere perfect for date night, Boka stakes its claim deservedly.

Old Town Pour House is top shelf, and it’s not just their jaw-dropping collection of craft beers. Everything here is high end. The upscale pub food (think duck confit nachos), classy wood interior, and mature but high energy ambiance. Don’t let the aesthetic fool you though, the Old Town Pour House is 100 percent a sports bar. So if your team is on TV, grabs some friends and head over to the Old Town Pour House.

In a neighborhood like Old Town, which dons a certain whimsical gravitas when the sun sets, you will most assuredly find a restaurant like the Pump Room. Clothed in low-mood lighting and all the swagger and swing of the 1930s and 1940s with a modern twist, the Pump Room absolutely oozes moxie. But again, the food might steal the show. Award-winning Chef Jean-Georges Vongerichten’s reinvented Pump Room classics (such as his melt-in-your-mouth red snapper) are what really complete the restaurant. He even makes sure that all the ingredients are locally sourced. If you’re looking to get dressed to impress, make the Pump Room your destination.