Check into Hotel Lincoln, former gay bathhouses now converted into hip and modern hotel suites in the Lincoln Park neighborhood.
The epic view of Lincoln Park from your hotel room will get you excited for the walk you're about to embark on to the north side of the park, where you will be able to choose between exploring the Lincoln Park Zoo, Garden, Conservatory, and/or the Lily Pool!
Find the Divvy Bike Station at the Theater on the Lake at Fullerton Avenue and take a ride up the lakeshore bike path to Montrose Harbor.
Grab some food at the Dock and cross your fingers for finding a good viewing area of gay men playing volleyball on Montrose Beach.
Once you've started getting restless again, check out Kayak Chicago's offerings back near the Montrose Harbor Divvy Station and choose the Lake Paddle, a 3-hour guided kayak tour through Lake Michigan with some seriously epic views of the city skyline.
Since you might be totally drained from paddling, biking or walking, give yourself a well-deserved taxi ride up Lake Shore Drive to the Waterfront Café for dinner. Or take the Red Line "L" from the Wilson stop to Granville stop and walk a few blocks east to this lovely, outdoor café right on the lakefront, which often has live music in the evenings (jazz, acoustic guitar, etc.) and is surrounded my festive string lights. Treat yourself to the fish & chips and a margarita or two.