You can join the masses cramming into Publican on its opening night in the West Loop, or you can hit a number of events around town, ranging from an all-out flashback bash to one for the fashion conscious:
THURSDAY
I love it when fashion shows cater to men and women, and this one spotlights the gear from new dress shop le Dress (1741 W. Division St., 773-697-9899) and dandy-man spot haberdash (1350 N. Wells St., 312-440-1300). The Dress & Dash Fall Fashion Show at Crimson Lounge pops off the latest looks, and guests will be treated to comped Cabana Cachaca rum cocktails, gift bags and more. 9-midnight. No cover, but call to get on the guest list just in case they try to give you drama.
The infamous Royster with the Oyster takes place next Friday, but tonight is the kick-off event. Head to Goose Island’s Clybourn location for free oysters with the purchase of any Goose Island Beer. 5:30-7pm. Free.
Engine, engine number 9, it's time for Black Sheep to shine! The seminal hip-hop duo from the 1990s makes a comeback with a live performance at Underground during its weekly Rewind! series. 10pm-4am. Cover varies.
Thursday Fall Series continues at Landmark Grill + Lounge, but you'll need to get there early for the freebies. They're offering comped Maker's Mark signature cocktails and seasonal bites from 7-9pm. There's also a $7 bar menu, created by Executive Chef Benjamin Browning, featuring organically grown meats and locally grown fruits and vegetables from Homegrown Wisconsin and Green City Market. Also, the signature cocktail to try is the Urban Cherry (Maker’s Mark Bourbon, homemade cherry syrup, blood orange bitters). 7pm-2am. No cover.
Chill out to rare grooves at Cat's Meow, as DJ Eric explores trip hop, reggae, nujazz, disco and more. The groovy, nostalgic setting is the perfect spot to nod your head to the beat as you chill out on the nice outdoor patio that's open until midnight. Also, $2 PBR and $3 Jameson shots. 9pm-2am. No cover.
FRIDAY
Be Bad to the Rhone simply because you can. Eno, the fab new wine bar tucked inside the InterContinental Chicago, debuts a new wine flight featuring Chilean, French and Napa Valley varietals. $15.
A fall-focused showcase highlighting the best in Chi-town fashion, music and the arts happens in the lobby of the W-City Center. Early arrivals get free bubbly (9-10pm), plus there will be a fashion show by Wicker Park's Funkshion Boutique (2121 W. Division St.). Also, bike enthusiasts can oooh and ahhh over the Criminal Customs choppers that'll be on display right outside of the hotel. DJ Uncle Milty spins. 8pm-1am. No cover.
SATURDAY
It's Oktoberfest time at Taste Food & Wine, which is showcasing a number of international beers, including Spaten, paired with cheese and sausages. 7-8:30pm. $20 in advance; $25 at door.
Get a lesson in the History of House Music as a number of legendary spin stars and vocalists take centerstage at the Congress Theatre (2135 N. Milwaukee Ave.) for what they're calling "one of the biggest dance parties ever." Just some of the talent: Mario "Smokin" Diaz, Lego, Wayne Williams, Joe Smooth, Farley "Jackmaster" Funk and Julian "Jumpin" Perez. Singers include Crystal Waters, Robin S., Shannon and Rochell Fleming. 6pm-3am. Call 312-559-1212 for tix ranging from $20-$49.50.
SUNDAY
The third-annual Andersonville Dessert Crawl happens—with two routes to choose from! I'm down for the Rainbow Route (3-6pm), but the Swedish Stroll (1-4pm) sounds just as good. Participants get to check out Andersonville's rich shopping district full of nifty little stores, boutiques and offbeat eateries. Each tour ends at In Fine Spirits for a wine-tasting event. Begins at the Swedish American Museum (5211 N. Clark St). 1-6pm. $25 in advance; $30 at door (if available). Event benefits the non-profit Andersonville Development Corp.; ticket info at 773-728-7552.
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