This eclectic neighborhood juxtaposes Victorian homes with modern new builds and trendy restaurants and bars alongside mom-and-pop shops along Damen and Milwaukee Ave. Pick up a pastry from Alliance Bakery, one of the oldest bakeries in Chicago, or drink in the spectacular skyline view along with your cocktail of choice at The Up Room on the 13th floor of the Robey Hotel. Walk the 606 trail, a repurposed rail line, for an elevated view of the area and adjacent neighborhoods.


Get lost in time in this quaint, historic area. Architecture buffs will love the Victorian-era mansions. Look out for the real cannon in the front yard of one of these homes and the “Wicker Park Castle”, a Queen Anne design complete with imposing columns of polished granite.