Guide To Living In Old Town Chicago

Originally a cabbage patch developed by German immigrants before the Civil War, Old Town carries a certain disheveled charm that dates to its formative years. St. Michael’s Church was one of the city’s few buildings to survive the Great Chicago Fire, contributing to the decision to maintain the area’s byzantine street layout while the rest of the city went to a simple north-south grid pattern after the 1871 blaze.

Ever since, the Old Town neighborhood has thrived as a quirky, Bohemian base. Gothic and Victorian touches abound on narrow, meandering one-way streets and main thoroughfares alike.

Here’s why living in Old Town gives you everything you’d want from big city living.

It’s Close to Everything

Wrigley Field and the heart of the Loop business district are less than 3 miles away. Closer than that is the burgeoning restaurant scene on Randolph Street. Closer still is River North and the Chicago Riverwalk, and North Avenue Beach is an easy stroll. If you really want to get away, you’re 20 minutes from O’Hare Airport. Three public train lines stopping in the neighborhood can carry you to points all around the city.

It’s a Dining Delight

There are a couple of great rib spots in Old Town. The area tends toward boisterous, divey destinations where character is always a star on the menu — but don’t let the lack of pretension fool you.

• Topo Gigio Ristorante has been serving modern Tuscan cuisine in the heart of Old Town for more than a quarter-century and has a terrific outdoor space.
• Kamehachi (“eight turtles” in Japanese) is the city’s first sushi restaurant. Its expansive menu options range from traditional to inventive.
• Adobo Grill is in its third decade, serving table-side guacamole and establishing itself as one of the most authentic Mexican dining spots in the city.
• Twin Anchors Restaurant & Tavern and the Fireplace Inn are venerable spots for ribs, with tons of fans, so they’re great places to start.

Making History

In 1924, the first gay rights organization in the United States was established in a home on North Crilly Court that is now a National Historic Landmark. In the 1960s, Old Town was the Midwest epicenter of the hippie counterculture. Now, The Second City comedy troupe stars.

It’s All About the Hangouts

• Old Town Pour House is a vast and upscale spot to celebrate your inner beer geek, with 90-plus varieties on tap.
• This should not be confused with the Old Town Ale House, which bills itself as “the best dive bar in Chicago” and gets few arguments.
• Benchmark is a classic sports bar with the plus of a “convertible” beer garden in addition to all the TVs and bar food you could want on game day.
• It’s really all about The Second City, the world-wide leader in improv comedy and the training ground for comic talents ranging from Alan Alda to Mike Myers, Stephen Colbert to Steve Carrell.

It’s Living Your Best Life

Nestled between the tonier Lincoln Park and Gold Coast enclaves, Old Town is the perfect, unassuming and thoughtful neighbor. It has two signature events — the annually concurrent and peacefully coexisting Old Town Art Fair in the Old Town Triangle and the Wells Street Art Festival just blocks away.

Tap into that friendliness with your own place in Old Town. Downtown Apartment Collective can help you find it. Browse our latest Old Town listings here.