Old Town

As its name suggests, you’ll find some of Chicago’s oldest buildings in Old Town. Many Victorian-era structures still exist, including St. Michael’s Church, one of only seven buildings to survive the Great Chicago Fire. The area on the Near North Side was first settled by German immigrants in the 19th century, and the farming community was dubbed, “The Cabbage Patch.” In the 1940s, the neighborhood sponsored an art fair called “Old Town Holiday,” and that name has stuck until today.

Old Town has seen a host of differing cultural influences over its history. It was a center for hippie culture in the 1960s, and it had a diverse gay community over this time. In the ’70s, Old Town became the center of Chicago folk music, and many of those institutions still exist today, including the Old Town School of Folk Music. In other ways, Old Town was known as a seedy area (home to many sex-industry businesses) in the 1970s. In the 2000s, the neighborhood became heavily gentrified.

Today, the neighborhood fuses the diverse influences of its past. It’s home to the popular Second City improv comedy theater, on-trend boutiques, and some classic watering holes.

Old Town Restaurants

Old Town offers a diverse restaurant scene with a combination of contemporary eateries and, you guessed it, old favorites. For example, Twin Anchors Restaurant & Tavern is not to be missed. The famous rib joint was one of the filming locations in Batman Begins, and Frank Sinatra used to be a regular at this once-speakeasy. Other Old Town Classic? Old Town Ale House has been kickin’ it since 1958. The dive is a favorite for Second City alums, and it’s open until at least 4 a.m. every night of the week. There’s also an array of delicious Mexican spots, classic steak joints, breakfast and brunch outposts, sushi, and Middle Eastern fare.

Old Town Tourist Attractions

If the Shedd Aquarium seems overwhelming, dip a toe into the waters at Old Town Aquarium. This small spot has fresh and salt-water fish and invertebrates to view and purchase.

Old Town Architecture

Architecture is one of Old Town’s most charming traits. There are an array of Chicago’s oldest examples of Victorian architecture here. Wander the streets to enjoy historic buildings, and be sure to stop by St. Michael’s Church. Built in 1855, the Gothic structure was one of only seven buildings to survive the Great Chicago Fire of 1871.

Old Town Theater

No serious Shakespeare here. Old Town is known for Second City, perhaps one of the best-known comedy clubs ever. The spot was started by students in 1959 and quickly grew a rep for improv comedy. The likes of John Belishi, Tina Fey, and Stephen Colbert can claim their starts here.

While Second City is now known for headliners, up-and-coming comics are getting their start just a block away at Zanies. It’s the third-longest-running comedy club in the U.S.

Old Town Festivals & Events

A nod to its original name, the Old Town Art Fair is still held every year in the neighborhood in June. The event brings more than 200 nationally acclaimed artists, a garden walk, and live music.