Old Town is a Chicago neighborhood that draws a lot of attention as it’s home to Victorian-style houses (think elegant brownstones) and the famed comedy club The Second City. Between the beauty and the laughs, the neighborhood is a highly accessible spot in the city with a wide variety of price points and a dining scene that’ll keep your restaurant bucket list on point. Is Old Town the place for you?

The Homes

Homes in Old Town

Old Town might be known for its brownstone walk ups, but those aren’t the only home styles in the neighborhood. The neighborhood also has high-rises with condos and more modern residential brick buildings. The prices in Old Town run the gamut. On the low end, you’ll find homes for around $169,000. On the high end, prices can go above $4 million. According to Neighborhoods.com, the median home sale price in the neighborhood is $370,000, which makes Old Town more affordable than a number of the surrounding communities. The median sale price in Gold Coast, Old Town’s eastern neighborhood, is $406,500. To the west, the median sale price in the Ranch Triangle is $580,000.

The Architecture

St. Michael's Church

Old Town is a mix of buildings built immediately after the Great Fire of 1871 and buildings (like St. Michael’s Church) that survived the famous blaze, according to Chicago Architecture Center. No matter where you live in the neighborhood, you’ll never be far from the striking architecture that defines the neighborhood. Other notable architectural gems in the neighborhood include Adler and Sullivan row houses and the Midwest Buddhist Temple, according to the report.

The Location and Accessibility

Sedgwick CTA Station

The neighborhood’s location is one of its most endearing features. The neighborhood is not right on the lake, accounting for its more reasonable home prices, but it’s still just a 20-minute walk from North Avenue Beach in neighboring Lincoln Park. In addition to the proximity to the lake, Old Town is also about 20 minutes outside the Loop via public transit or car ride.

Being so close to downtown, Old Town has excellent access to public transportation. CTA riders can hop on the Brown, Purple, and Red lines, which snake throughout the city. Plus, a number of bus lines run through the neighborhood. If you’re a car owner, you’ll have better luck finding street parking than you would downtown, although Chicago parking is always a competitive gamble.

Pedestrians and bicyclists will appreciate the neighborhood’s quieter side streets, as well as the nearby Lakefront Trail. 

The Food

Outdoor seating in Old Town

Eating out in Old Town is a delicious experience. For a hearty meal and beer, you have Old Town Pour House and Twin Anchors. Old Town Pour House has 90 different craft beers on tap and a filing menu complete with all of the bar food staples. Twin Anchors—recognizable as a filming location from “The Dark Knight”—dates back to 1932 and serves a mean plate of ribs.

Sushi lovers in Old Town will quickly become regulars at Kamehachi, a longstanding neighborhood establishment. 

Alinea, located on the on the western edge of Old Town, is the ideal spot for an indulgent and trendy meal out. The Michelin-starred restaurant promises not just a meal but an experience. Choose from The Kitchen Table, The Gallery Menu, or The Salon Menu. Each tasting menu brings uniquely prepared and lavishly presented dishes to the table. Alinea is, naturally, only open to reservations.

The Entertainment

Second City in Old Town

The Second City, Old Town’s biggest claim to fame, is a comedy club and incubator that has helped launch the careers of comedic greats like Dan Aykroyd, Steve Carell, Tina Fey, and Amy Sedaris. You can catch drinks and a show at the comedy club on nearly any given night. 

If live shows are your idea of a weekend highlight, Old Town is the place to be. In addition to The Second City, the neighborhood is also home to A Red Orchid Theater and comedy club Zanies.

When you need a break from laughing yourself into stitches, the neighborhood’s shopping scene is another major draw. Get all of the sweets you can handle at The Fudge Pot, and fill your spice rack at The Spice House. Aquarium enthusiasts or even just curious browsers will love Old Town Aquarium, a colorful stop for all things underwater.