Welcome to Old Town
Old Town blends historic Chicago character with legendary comedy, lively dining, and walkable neighborhood streets just north of downtown. Explore Victorian-era architecture, spend an evening along Wells Street, catch a show at Second City, or continue toward the lakefront and nearby Lincoln Park.
At a Glance
Get a quick overview of Old Town, from its historic streets and legendary comedy scene to dining, nightlife, walkability, and easy access to nearby Chicago neighborhoods.
Best For
Comedy, nightlife & history
Highlights
Comedy • Dining • Architecture
Walkability
Excellent
Getting Around
CTA trains & buses
Local Tip
Plan dinner before a comedy show
Our Recommendations
🏨 Stay
Old Town has limited hotel options within the neighborhood, but nearby River North, Gold Coast, and Lincoln Park offer convenient places to stay within easy reach.
🍽 Eat
Explore casual neighborhood restaurants, popular brunch spots, cocktail bars, and pre-show dining along Wells Street and throughout Old Town.
☕ Coffee
Take a break at a neighborhood café or coffee shop while exploring Old Town’s historic streets, local businesses, and nearby attractions.
🎭 Don't Miss
Catch a comedy show, stroll the Old Town Historic District, explore Wells Street, and discover landmarks such as historic St. Michael’s Church.
Explore Old Town
Experience Old Town through its restaurants, historic streets, entertainment, shopping, and nightlife, with Wells Street at the center of much of the neighborhood’s energy.
🍽 Where to Eat
Discover casual neighborhood restaurants, weekend brunch spots, pre-show dining, cocktail lounges, and late-night options along Wells Street and beyond.
🎭 Things to Do
Catch a comedy show, explore Victorian-era streets and historic landmarks, stroll Wells Street, or continue toward nearby Lincoln Park and the lakefront.
🛍 Shopping
Browse local shops, boutiques, and neighborhood businesses while exploring Wells Street and Old Town’s walkable commercial corridors.
🌃 Nightlife
Make a night of it with comedy, neighborhood bars, cocktail lounges, and lively gathering spots that keep Old Town energetic after dark.
Discover More
Explore more guides, recommendations, entertainment, and local discoveries to help you experience the best of Old Town.
Continue Exploring
Ready to explore beyond Old Town? Discover nearby neighborhoods with lakefront attractions, acclaimed dining, shopping, nightlife, and more Chicago experiences just minutes away.
Lincoln Park
Head north for Lincoln Park Zoo, beautiful green spaces, lakefront recreation, neighborhood dining, and tree-lined residential streets.
Gold Coast
Head toward the lake for historic architecture, elegant streets, luxury shopping, upscale dining, and easy access to the waterfront.
River North
Continue downtown for acclaimed restaurants, rooftop bars, galleries, nightlife, architecture, and easy access to the Chicago River.