Three Cities Social Club Opens in Wicker Park, Expanding Chicago’s Premier Membership-Based Community Club
In a city defined by neighborhoods and the communities that anchor them, Three Cities Social Club has officially opened its second Chicago location in Wicker Park, marking a significant expansion for the fast-growing, membership-based social club.
Located at 1643 N. Milwaukee Ave., the 10,000-square-foot, bi-level clubhouse joins the brand’s flagship in River North, reinforcing its presence in two of Chicago’s most culturally vibrant corridors. The expansion reflects a broader shift in how urban professionals seek connection, moving beyond traditional coworking spaces and nightlife venues toward environments designed with intention.
Founded in 2022 by former professional soccer player and Merrill Lynch alum Draymond Washington, alongside co-founder Ali Washington, Three Cities was born out of a personal search for meaningful community. What emerged is a private club structured around three pillars: altruism, connection, and culture.
“We built Three Cities for people who want to meet others with purpose,” Washington said. “The design encourages connection that happens organically, through shared experiences rather than transactional networking.”
A Modern “Third Space” in Wicker Park
The new Wicker Park clubhouse is designed to function as both a social and professional hub. Amenities include:
- An outdoor terrace
- Pool table
- Fitness center and showers
- Boardroom and private offices
- Dedicated dining room
- Flexible open work areas
Like its River North counterpart, the space operates on a BYOB and BYOF model, fostering a relaxed, communal atmosphere that encourages members to host gatherings, collaborate on projects, or simply unplug from the demands of the city.
Membership includes access to more than 20 curated events each month, ranging from intimate dinners and creative workshops to neighborhood excursions and volunteer initiatives. The programming underscores the club’s emphasis on intentional engagement over passive attendance.
The Business of Belonging
Three Cities enters Wicker Park at a moment when Chicago’s professional class is reevaluating where and how community is built. As hybrid work reshapes daily routines, demand for curated, values-driven gathering spaces has grown.
Membership begins at $249 per month for individuals and $299 for couples, granting access to both clubhouses, daily entry from 7 a.m. to 1 a.m., and all amenities. Prospective members can join a waitlist or schedule tours through the club’s website.
With two thriving locations and a values-first framework, Three Cities Social Club is positioning itself as more than a venue. It is an ecosystem, designed to cultivate belonging in a city that continues to evolve.
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