Welcome to Old Town

A charming, historic neighborhood where classic Chicago character meets modern boutique living.

Old Town is known for its Victorian-era architecture, tree-lined streets, and a warm, village-like feel. From iconic comedy clubs to independent shops and award-winning restaurants, the neighborhood blends timeless charm with lively urban energy.

Beloved by longtime residents and newcomers alike, Old Town offers walkability, cultural richness, and quick access to the lakefront and downtown. Its inviting atmosphere and community-focused spirit make it one of Chicago’s most cherished places to call home.

What to Love

Beautiful historic homes and picturesque streets
The famed Wells Street shopping and dining corridor
A vibrant arts and entertainment scene
Easy access to the lakefront, parks, and public transit
A true neighborhood feel in the heart of the city

Local Lifestyle

Old Town moves at an easy, pleasant pace. Mornings bring locals strolling to neighborhood cafés, browsing small shops, or jogging toward the lakefront. Weekends are often filled with outdoor markets, sidewalk dining, and community festivals.

The neighborhood offers the perfect blend of relaxed charm and lively culture. With theaters, comedy clubs, cozy wine bars, and inviting green spaces, Old Town supports a lifestyle that is as comfortable as it is connected.

Dining, Entertainment & Shopping

Old Town offers a wide range of beloved local destinations:

The Second City – Chicago’s iconic comedy institution
Topo Gigio – A classic Italian favorite with a bustling patio
Old Town Ale House – A legendary neighborhood bar with history and personality
Kanela Breakfast Club – A relaxed brunch spot with a Greek-inspired twist
Wells Street Boutiques – Independent shops offering fashion, gifts, and specialty goods

The neighborhood’s intimate scale makes it ideal for exploring cafés, eateries, and shops at a leisurely pace.

Things to Do

Old Town has something to enjoy year-round:

Old Town Art Fair – One of Chicago’s oldest and most beloved summer festivals
Wells Street Festival – A weekend of music, food, and local artisans
Lincoln Park – Just steps away, offering trails, green space, and lakefront access
Historic St. Michael’s Church – A stunning landmark known for its architecture and history
Zanies Comedy Club – Another iconic venue for stand-up and live performances

Schools

Old Town is served by Chicago Public Schools and offers access to public, private, and specialty learning options:

Lincoln Park High School
Manierre Elementary School
Immaculate Conception St. Joseph School
British International School of Chicago – Lincoln Park

Families appreciate the neighborhood’s strong community feel and educational diversity.