Welcome to Old Town
A historic Chicago neighborhood with highly desirable real estate
Old Town is a stunning, walkable neighborhood with unmatched vintage charm. This small community is brimming with history, with roots dating back to the mid-19th century that can be seen everywhere, from the brick-lined alleys to its busy main street. While Old Town holds onto its rich historical roots, the community also has a vibrant atmosphere that keeps it young and modern. The neighborhood thrives on a mixture of comedy venues, shops, restaurants, bars, and theaters. With its clean, peaceful streets and abundant entertainment options, it’s easy to see why people love calling Old Town home.
Residential areas offer pedestrian-friendly, narrow, tree-lined streets teeming with historic homes, highly desirable Victorian-era residences, and a string of luxury high-rises with stunning lake views. You’ll also find a diverse selection of townhomes, single family homes, and vintage walk-up apartments lining the charming streets.
What to Love
- A stunning selection of homes
- An active community with year-round events
- Quality shopping and dining options
Local Lifestyle
Residents of Old Town love the lively atmosphere that comes with this charming, historic spot. The myriad of specialty shops offering handmade goods, vintage finds, and music blend well with the assortment of family-owned restaurants, seasonal taverns, ale houses, and comedy clubs to create a well-rounded selection of fun and excitement. Old Town is the birthplace of American improv and is home to The Second City, renowned for attracting first-class comedians like Bill Murray, Chevy Chase, Mike Myers, Tina Fey, and Steve Carrell.
The tranquil residential streets lined with a unique blend of modern, luxurious, and historical homes, townhomes, and apartments make Old Town one of Chicago's most affluent residential districts. Add in the mixture of green spaces, parks, boutiques, and late-night buzz, and you’ll understand why so many love this neighborhood.
Dining, Entertainment & Shopping
Residents will find an assortment of shopping and dining options, from unique boutiques to a wide array of excellent restaurants. The walkable main strip makes it easy to get from one spot to another, and the variety of cuisines offered in nearby restaurants are sure to please even the pickiest of palates.
Topo Gigio Ristorante offers a warm atmosphere and traditional Tuscan-inspired cuisine. This cozy spot has been a neighborhood favorite for over 25 years and offers fresh, flavorful fare. Their extensive wine list is perfect for pairing with every dish.
Orso’s is another excellent Italian spot offering old-school dishes. The romantic setting is perfect for date nights, and the attentive staff makes everyone feel welcome. Feast on classics like lasagna bolognese, chicken parmigiana, and pizza here.
Kamehachi offers Japanese cuisine in a relaxed setting. The first of its kind in Chicago, this sushi bar will satisfy your tastebuds and leave you feeling like a part of the community.
Gussie’s Handmade Italian offers a modern spin on classic Italian dishes. The light and airy setting is perfect for their signature Sunday brunch, which features scratch-made entrees and delectable pastries.
Things to Do
Old Town’s array of exciting amenities only enhances the area’s attractiveness. On any given day, residents can enjoy visiting a local park, attending a community event, hiking a nearby trail, and more.
The Old Town Art Fair is an annual event held in June that brings over 200 nationally acclaimed artists together in one location. The fair attracts more than 30,000 visitors and features a garden walk, live music, food trucks, children’s activities, and plenty of fantastic artwork. The Wells Street Art Festival is another annual event that draws in massive crowds. This festival boasts live entertainment, cuisine from local restaurants, handcrafted libations, and two days of community fun. All gate donations benefit local community organizations.
The Old Town Tree Lighting at Burton Place Park is a coveted neighborhood holiday event. Complimentary cocoa and sweet treats are provided by local businesses to attendees, who can sit back and enjoy live music from youth choruses or take their children to meet Santa Claus. The event culminates with the annual tree lighting, which transforms the park into a festive and colorful oasis. This beloved event is put together by the Old Town Merchants and Residents Association, which organizes various events throughout the year to keep the community spirit alive.
Schools
