As you can tell by the name alone, Boystown has long been a nexus for Chicago’s LGBT community. But word of this pocket of East Lake View’s awesomeness has spread, and the stroller contingent now brings its A-game on weekend mornings. It’s no surprise: the neighborhood boasts excellent restaurants, kitschy shops, and beautiful architecture—all close to the lake.
1. The Annoyance Theatre & Bar
You just might see the next Stephen Colbert or Jane Lynch, both alums of this renowned comedy spot. theannoyance.com
2. Hawthorne Place
This street between Broadway and Lake Shore Drive may be only one block long, but, oh, what a beautiful stretch of mansions it is.
3. Kit Kat Lounge & Supper Club
Where else can you catch a drag queen diva show with a side of comfort food? (Avoid the Saturday night bachelorette party crowds and hit Burger & Beer Bitch Tuesday.) kitkatchicago.com