Old Town
Neighborhood Guide
Old Town blends historic character with one of Chicago's most concentrated social corridors. Wells Street anchors the neighborhood, keeping dining, nightlife, and cultural venues within a short walk and allowing weekends to unfold without complicated planning.
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Hotel Recommendations
Staying near Old Town keeps weekends tightly connected. While accommodations often sit just outside the immediate corridor, the neighborhood's compact layout allows guests to move easily between dining, nightlife, and event venues without relying heavily on rideshare.
Bachelor & Bachelorette Weekends
Old Town is well suited for social weekends that blend brunch, casual dinners, and late nights in one place. Groups often start the day with relaxed meals before settling into Wells Street for the evening. Gussie's Italian and La Fournette provide dependable gathering points early on.
As the night builds, Old Town Ale House and nearby spots keep energy high without spreading the group out. The density of venues makes it easy to move together and adjust plans on the fly.
Wedding Weekend Flow
Wedding weekends in Old Town feel classic and social. Welcome drinks and rehearsal dinners frequently take place at familiar neighborhood institutions such as Topo Gigio, Orso's, and Kamehachi. Private parties at The VIG offer flexibility without formal staging.
Comedy and cultural programming through The Second City often becomes part of the weekend flow, giving guests an easy group activity between events.
Holidays & Neighborhood Events
Holiday weekends amplify Old Town's street level energy. Signature events like the Old Town Art Fair and Wells Street Art Festival bring crowds into the neighborhood while maintaining its local character.
Ongoing coordination and seasonal programming from the Old Town Triangle Association, along with events at the Second City, shape the neighborhood's annual rhythm and keep weekends active without losing cohesion.
Where to Eat & Drink
Old Town's dining scene is rooted in long standing favorites that work well for groups. Meals tend to stretch, conversations linger, and movement between venues stays minimal.
Nearby Attractions
Cultural institutions and neighborhood festivals define much of Old Town's weekend activity. Old Town's historical buildings and architecture anchor the scene, while nearby restaurants and recurring events along Wells Street give visitors easy daytime and evening options.
Travel Times from Old Town
Estimated travel times to our harbor locations. We recommend arriving 30 minutes before your scheduled departure.
31st Street Harbor
3155 S. Lake Shore Dr., Chicago
Burnham Harbor
1559 S. Lake Shore Dr., Chicago
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