Nestled just north of downtown Chicago, Old Town is a vibrant neighborhood steeped in history, charm, and cultural significance. Known as the birthplace of modern American improv and home to some of the city’s most legendary entertainment venues, Old Town seamlessly blends vintage allure with a buzzing modern energy. With its boutique-lined streets, top-tier restaurants, and beautiful architecture, this neighborhood offers a unique and unforgettable Chicago experience.
Old Town is synonymous with the rise of American improv, and the iconic The Second City is the neighborhood’s crown jewel. Comedy legends like Tina Fey, Bill Murray, Gilda Radner, and Steve Carell began their careers here, and you can catch live shows showcasing the city’s best up-and-coming talent every night of the week.
For music lovers, the Old Town School of Folk Music provides classes, concerts, and workshops in a variety of musical genres. Whether you’re taking a lesson or enjoying a performance, this historic institution is a must-visit for its intimate and inspiring vibe.
Old Town’s culinary scene is a delightful mix of historic establishments and trendy hotspots:
Twin Anchors: This former speakeasy is a legendary spot for barbecue ribs, once frequented by Frank Sinatra himself.
The House of Glunz: Chicago’s oldest wine merchant, serving fine wines and spirits for over 120 years.
Old Town Ale House: A quirky, art-filled watering hole beloved by locals, Second City cast members, and even Anthony Bourdain.
For a more contemporary vibe, head to Wells Street, the neighborhood’s main drag, where you’ll find lively spots like:
Happy Camper: A fun pizza joint with an energetic atmosphere.
Broken English Taco Pub: Vibrant décor and delicious tacos make this a local favorite.
Gussie’s Handmade Italian: Cozy Italian comfort food in a welcoming setting.
For dessert, don’t miss The Fudge Pot, a family-run shop crafting handmade chocolates since 1963.
Old Town is a shopper’s paradise with its mix of unique boutiques and specialty stores. Explore vintage finds, on-trend apparel, and handmade goods along Wells Street and beyond.
Each June, the neighborhood hosts the Old Town Art Fair, a beloved outdoor festival featuring over 200 nationally acclaimed artists, live music, and a garden walk through the historic Old Town Triangle.
Old Town is one of Chicago’s most picturesque residential areas, with streets lined by charming brick and stone homes. The Old Town Triangle, designated as a historic district, showcases some of the city’s finest examples of Victorian and Italianate architecture. The neighborhood’s history dates back to the mid-19th century when German settlers first arrived, and much of its vintage charm has been carefully preserved over time.
Old Town’s proximity to Lake Michigan makes it an ideal location for outdoor enthusiasts. Residents can easily access the lakefront trail, beaches, and parks for jogging, biking, or simply soaking up the views. Nearby Lincoln Park offers a lush escape with its gardens, ponds, and the Lincoln Park Zoo.
Getting around Old Town is easy with a variety of public transit options:
CTA Brown Line: The Sedgwick station provides quick access to downtown and other parts of the city.
CTA Buses: Routes like the #22 Clark, #156 LaSalle, and #72 North connect the neighborhood to key destinations.
Divvy Bikes: Bike-sharing stations are scattered throughout the area, making it a breeze to explore on two wheels.
Old Town is home to some of Chicago’s most prestigious schools, attracting families who value education:
Franklin Fine Arts Center: A CPS magnet school offering an arts-focused curriculum.
Lincoln Elementary School: Consistently ranked as one of the top public schools in the city.
Walter Payton College Prep: A highly selective public high school recognized for its academic excellence.
Whether you’re laughing at a live show, enjoying ribs in a historic speakeasy, or wandering through charming streets lined with boutiques, Old Town offers an unforgettable blend of history, culture, and modern-day vibrancy. It’s a neighborhood that invites exploration at every turn, making it a true Chicago gem.
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