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The Old Town Triangle is the quintessential and most recognizable area of Old Town. With shops, art, shows, and dining, this is the heart of the neighborhood. We’ve put together a list of sights to see and places to go in the Old Town Triangle.

Restaurants in Old Town

Nookies is an Old Town restaurant staple, sitting in the heart of the neighborhood since 1973. It has since expanded to multiple Chicago locations, but the original still sits on Wells Street and offers delicious comfort food. Great options include meatloaf, burgers, and chicken and steak dishes.

1959 Kitchen and Bar is inside of The Second City and is the perfect place to grab a drink and a bite to eat before a comedy show. With its chic and retro decor, this gastropub has a large craft beer selection along with filling entrees such as fried chicken, short rib tacos, and shrimp and grits.

Art in Chicago’s Old Town

Old Town is a neighborhood full of arts and culture. The Old Town Triangle Association offers art classes for both beginners and advanced students including figure drawing, oil painting, and watercolor painting.

The Old Town Art Fair is an annual festival held every summer in Chicago. The festival includes artists exhibits and booths, food, music, and a garden walk that allows you to walk through the beautiful gardens in the neighborhood houses.

Entertainment in Old Town

Old Town is known for having the best comedy clubs in Chicago.

The Second City is a can’t miss comedy stop. The world-renowned comedy club has alumni now performing on Saturday Night Live, including Steve Carell, Tina Fey, Jordan Peele, and many more people. Check out “The Best of Second City” on Mondays and weekends to get a taste of the Second City spirit and watch a performance of the best sketches, songs, and improv moments from the past fifty-eight years of Second City history.

Check out the UP Comedy Club where you can watch Second City performances aside from the Second City mainstage.

Zanies Comedy Club is the place to be for stand-up comedy lovers. Past acts include Jerry Seinfeld, Jay Leno, Tim Allen, and Chelsea Handler.

Shopping in Old Town

The Greenheart Shop is a fair trade store on North Wells Street that sells a wide assortment of products including clothing, kitchenware, accessories, and artisan jewelry. They sell products that are eco-friendly and socially responsible and all of their products are in line with the shop’s philosophy.

Adelaide is a luxury women’s clothing store with many European-imported clothing, handbags, jewelry, and shoes. This sophisticated boutique has been in Old Town since the early 1990’s and is worth stopping by.

If you’re a runner, Fleet Feet Sports Old Town is the place to be. With the latest running apparel, shoes, and gear, you’ll always be prepared for your next run if you stop by Fleet Feet. They offer free injury screenings and yoga classes specifically for runners. Don’t forget to check out one of the weekly running events such as Monday night fun run and Tuesday night Chick’s Night.

Cafes in Chicago’s Old Town

Cocoa + Co is a cafe and bakery offering decadent chocolate treats, hot cocoa, and coffee. This chocolate-lover paradise has a sleek modern design and is the perfect place for a grab and go chocolate pastry.

Eva’s Cafe is a brick-walled coffee shop on North Wells Street with coffee, tea, sandwiches, and bagels. This cozy cafe was designed to feel like home with exposed brick, warm red walls, and cozy chairs perfect for a warm cup of joe and a book.

Now that you know the highlights for the Old Town Triangle, it’s time to check it out for yourself. If you’re in the market for a new Chicago apartment or condo and want to explore the Old Town Triangle more in depth, click the link below!