Wedged between Lincoln Park and the Gold Coast, Old Town offers the best of both of these neighborhoods and shines with a serious charm of its own. Appropriately named, this community boasts a big chunk of Chicago history, with many of its homes and buildings dating back to the Victorian era.

You’ll notice that some of Old Town’s streets don’t fit into Chicago’s navigational grid; that’s because they predate the Great Chicago Fire. In fact, there’s even a landmark here that went untouched by the catastrophe. That’s right, St. Michael’s Church was one of the few buildings still standing after the flames.

Years after the Great Fire, Old Town became a melting pot for artists and musicians. Small studio spaces were built to house students of the nearby Art Institute of Chicago and folk musicians like Janis Joplin and Mama Cass frequented local venues. Eventually things calmed down and the energetic scene became more of a mecca for families and young urban professionals.

Despite it being one of the smaller neighborhoods of Chicago, Old Town offers the world at your fingertips. The streets are lined with a diverse array of restaurants, coffee houses and eclectic shops. Boutiques offer a more personalized shopping experience than those at big-name department stores and specialty shops range in everything from exotic spices to rare books.

In recent years, a few chain restaurants have reared their way into Old Town, but local cafes and authentic eateries still thrive in this historic spot. Neighborhood pubs are not only inviting, but also a great place to mingle after catching a show at the world-famous Second City Theatre. Cast members of Second City frequent some of these bars and have been known to strike-up conversations with theater enthusiasts. When you do feel like breaching the border of Old Town, you can hop on the Brown or Purple line at the North Sedgwick El station. 

he majority of residential Old Town is compromised of townhomes and single-family brick-style units. Most homeowners here have gone to great lengths to renovate and restore these homes to resemble their original structures. Because of its vintage charm and close proximity to the Loop, this neighborhood is prime real estate for the affluent. However, rents are still a notch below those of the Gold Coast.