Old Town

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Old Town is one of Chicago’s most charming and character-filled neighborhoods, known for its historic architecture, tree-lined streets, legendary comedy clubs, and vibrant dining scene. Located just north of downtown, Old Town blends classic Chicago character with an energetic nightlife and easy access to the lakefront, Lincoln Park, and the Magnificent Mile.

It’s a favorite for visitors who want history, entertainment, and walkability without the intensity of the Loop or River North.

Old Town offers a mix of culture, entertainment, and neighborhood exploration.

Highlights include:

• Second City Comedy Club — World-famous improv and comedy where many legends got their start
• Old Town Historic District — Victorian-era homes and quiet residential streets
• Wells Street — The neighborhood’s main corridor for dining, bars, and nightlife
• St. Michael’s Church — A historic landmark dating back to the 1800s
• Nearby Lakefront Access — Easy walks to North Avenue Beach and Lincoln Park

Old Town’s dining scene is lively and social, especially along Wells Street.

What you’ll find:

• Casual neighborhood restaurants
• Popular brunch spots
• Bars and cocktail lounges
• Late-night dining options tied to the comedy scene

It’s a great area for pre-show dinners, weekend brunch, and relaxed nights out.

Old Town has limited hotel options directly within the neighborhood, but it’s surrounded by excellent places to stay.

Best nearby areas include:

• River North — wide range of hotels and nightlife
• Gold Coast — upscale, walkable, and close by
• Lincoln Park — quieter, residential feel

Old Town is ideal if you want central access to entertainment, dining, and multiple neighborhoods.