Friday-Sunday: Chicago's LGBT community and its supporters flood the streets of Boystown for their biggest wekeend of the year. The two-day Pride Fest -- which boasts two stages of live music and drag shows plus loads of food and drink vendors -- leads up to the always over-the-top Pride Parade on Sunday. The fest is located at the corner of Halsted St. and Waveland Ave. The parade route begins at Halsted St. and Belmont Ave. Festival times: Fri., 4-10pm, Sat. 11am-10pm, $7 donation before 5 p.m.; $10 after, Parade: 12-3pm, Free
Friday: You and your pooch can unwind after a long day at the office on National Bring Your Dog to Work Day at Franklin Tap's "Yappy Hour." From 5pm to midnight, the Tap is serving up $5 appetizers and a canine-themed cocktail to celebrate the holiday -- the "Mutt-tini." 325 S. Franklin
Friday and Saturday: It's never too early to start celebrating the holidays. Uncle Fatty's Rum Resort is marking the half-way to Christmas mark this weekend with a festive holiday-themed bash. Live cover bands, a bikini contest --with a $1,000 grand prize -- and the unveiling of ten new frozen cocktails should add a little jingle to your night. Bring a new or gently used toy to benefit Toys for Tots and get your $5 cover charge waived. 2833 N. Sheffield Ave
Friday and Saturday: Washington Redskins QB and Chicago native Donovan McNabb is coming to town for a two-day weekend events series to benefit the Donovan McNabb Fund. Events include a white tie affair at China Grill, a rooftop party at Lakeshore Athletic Club and a late-night bash at Hotel W. Weekend passes are $40.
Saturday: Chicagoans will don their most impressive headwear and dance 1,000 feet above the city skyline at the Lookingglass Junior Board's Madhatter's Ball at the John Hancock Observatory. Madhatters can look forward to appetizers and cocktails as well as live music and performances. 9pm, 875 N. Michigan Ave, Tickets are $85
Saturday: Here's your chance to be part of Jeremy Piven's entourage this at the official afterparty for the Piven Theatre Workshop's 40th Anniversary Gala. Piven and nightlife maven Billy Dec will be hitting up Rockit Bar & Grill for the party after the party, which includes Grey Goose cocktails and snacks from Rockit's kitchen. 9-11pm, 22 W. Hubbard St, $20 donation
Saturday and Sunday: Green Music Festival hits Wicker Park this weekend to celebrate all things eco-friendly. In addition to two full days of live tunes, Green Fest houses an array of green-themed food and retail vendors. Damen and North Avenues, Sat. and Sun., 12-10pm, $5 suggested donation
Sunday: Custo-Barcelona rocks its summer fashion show at Sushi Samba Rio. Catch a glimpse of the hottest summer fashions sported by Ford and Factor models. Tsi-tsi-ki Felix of Telemundo Chicago hosts this fashion bash which also features Absolut cocktails and tasty treats from Sushi Samba Rio's house chef Dan Tucker. 504 N. Wells, 5-10pm, Tickets start at $45