Chicago: Nightlife

Debonair Social Club Hipsters and yuppies collide at this intimate video club where a color-changing lightbox and thematic videos set the mood. Wicker Park; 1575 N. Milwaukee Ave.; 773-227-7990; www.debonairsocialclub.com
trendy | dancing | nightclub

Juicy Wine Co. Hipster oenophile Rodney Alex has struck gold in the form of this understated gem where local scenesters come for gobs of yummy cheese and an unbelievable wine selection. River West; 694 N. Milwaukee Ave.; 312-492-6620; www.juicywine.com
trendy | lounge | wine bar

Lumen Dazzling light shows and progressive DJs lure clubby crowds to this meatpacking district up-and-comer. Meatpacking District; 839 W. Fulton Market; 312-733-2222; www.lumen-chicago.com
trendy | dancing | nightclub

Pops for Champagne Great jazz exists city-wide in Chicago, but Pops tops them all when it comes to atmosphere. The elegant champagne bar (over 100 varieties on offer) lures thirty- and forty-somethings with fizzy libations and primo people watching in a simultaneously modern and classic space with cool blue accents and state-of-the-art sound complementing the building’s original stone walls and low ceiling. River North; 601 N. State St.; 312-266-7677; www.popsforchampagne.com
smart splurge | lounge | live music

Sidetrack This perennial gay favorite is a sprawling video bar with one of the best rooftop decks in town. Don’t miss Monday’s raucous showtunes night. Lakeview; 3349 N. Halsted St.; 773-477-9189; www.sidetrackchicago.com
gay | patio | video bar

The Green Mill Al Capone is among the legendary patrons to have climbed into one of the giant curvy booths at this legendary jazz joint and speakeasy. Uptown; 4802 N. Broadway; 773-878-5552
jazz | historic | live music

Zebra Lounge The ubiquitous zebra theme is the only distraction at this laid-back piano bar where unpretentious Gold Coasters cobble together for conversation and live music. Gold Coast; 1220 N. State Pkwy.; 312-642-5140
lounge | bar | live music