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DAY TWO: FREEWHEELING
Orange (Lakeview: 3231 N. Clark St; 773-549-4400; and Downtown: 75 W Harrison St; 312-447-1000; $8-10) has the market cornered on Chicago's best brunches -- nutty and inspired pancake flights, anyone?
If you?re staying downtown, rent a bike at Navy Pier. If you?re staying closer to Boystown, rent bikes from gay-owned Out Spoke'n (1113 W. Belmont Ave; 773-404-2919) and bike the path along Lake Michigan, which runs from the Loop to the Northside, which is about six miles. Some sites along the way include Lincoln Park Zoo (2200 N. Cannon Dr.; 312-742-2000), one of the oldest and still free zoos in the nation; the excellent Lincoln Park Conservatory (2391 Stockton Dr.; 312-742-7736), and a few decent public beaches. If it's raining, step inside Chicago Historical Society (1601 N. Clark St.; 312-642-4600), which traces the development of Chicago through numerous exhibits and installations.
Stray off the path for lunch at gay institution, the Melrose (3233 N. Broadway St; 773-327-2060; $5-18), which serves inexpensive diner food 24 hours a day.
Spend the afternoon shopping in Boystown. Gay-oriented retail and dining options are sprinkled along Halsted and Broadway. Some quandaries for shoppers intent on squandering include Bad Boys (3352 N. Halsted St.; 773-549-7701), Chicago's premier gay outlet for sportswear and clubwear; His Stuff (5314 N. Clark St.; 773-989-9111), which markets itself to upscale gay men and metrosexuals; Laundre (5205 N. Clark St.; 773-769-2890), a minimalist white showroom offering men's clothing and a smaller women's line; Gay Mart (3457 N. Halsted St.; 773-929-4272), a knick-knack boutique offering gifts, cards, shirts, and a wild assortment of everything gay.
For gay books: Unabridged Books (3251 N. Broadway St.; 773-883-9119) is the leader. Women and Children First (5233 N. Clark St; 773-769-9299) is an excellent lesbian/feminist bookstore. Sex-positive shops of note, which feature condoms, lube and toys, include: Batteries Not Included (3420 N. Halsted St; 773-945-9900) and the excellent women-owned Early to Bed (5232 N. Sheridan Rd.; 773-271-1219).
For cafe culture, try Caribou Coffee (3300 N. Broadway St; 773/477-3695, or 3500 N. Halsted St; 800-CARIBOU), a friendly place to sip, read, and chat. They are both very happening, although if you're looking for something without corporate branding, try Pause (1107 W. Berwyn Ave; 773-334-3686) which is gay-owned and operated, albeit located a little further north.
Just steps from all the hot bars, FireFly (3335 Halsted St; 773-525-2505; $9-27) is a hot little romantic spot with great martinis, perfect filets, and legendary desserts.
You did the old favorites last night, so tonight sashay off to hit the city?s freshest, hippest hotspots; Scarlet (3320 N. Halsted St; 773-348-1053), a sleek red and exposed brick drinking den in the space that formerly housed tired piano bar Gentry?s; and sleek Minibar (3341 N. Halsted St; 773-871-6227), home to the city?s stand and model set.
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