From neighbourhood pubs to trendy lounges, Chicago offers plenty of places to enjoy your favourite elixir.

Wine Bars

404 Wine Bar - Stepping inside this neighbourhood lounge is like walking into a private home. Leather couches, fireplaces and exposed brick walls are complemented by a wine list that features more than 100 labels from around the world. A canopy of trees covers the outdoor patio to offer a romantic setting for you and your sweetheart.
2856 N. Southport

ENO - Wine aficionados (and novices, for that matter) will feel at home in this exquisite lounge on Michigan Avenue. Wine, cheese and chocolate are on the menu to indulge the senses and a knowledgeable staff is eager to recommend pairings and offer insights on the nearly 500 varietals of wine.
505 N. Michigan

The Tasting Room at Randolph Wine Cellars - Rarely do you find an intimate setting with a sweeping view of the city skyline. But that’s what the Tasting Room delivers, along with over 100 wines availably by the glass, flight or tasting. Perhaps that’s why this lounge was voted “most romantic bar” in Chicago.
1415 W. Randolph

Vintage Wine Bar - While it may be nestled in one of Chicago’s trendiest neighbourhoods, you won’t find any dress codes or pretenses in this lounge. Instead, you’ll find a casual, yet hip, atmosphere where conversation centres around friends, not the wine.
1942 Division

VOLO Restaurant – Wine Bar - This lounge defines “urban vintage” with its chic design and cosy setting. If a romantic setting is what you’re after, then enjoy your wine in the heated cabana garden — arguably one of the city’s best dining spaces. VOLO also makes pairing select dishes with eclectic wine flights a breeze for guests to find their own palate.
2008 W. Roscoe

Webster’s Wine War - Chicago’s oldest wine bar is home to over 35 wines by the glass and over 500 wines by the bottle from around the world. While its setting may feel like an old-world library, Webster’s is anything but stuffy. Visitors will find an atmosphere that’s perfect for conversation among friends, or a quiet evening with your sweetheart.
1480 W. Webster

Lounges

Elm Street Liquors - A rare find in Chicago’s Gold Coast neighbourhood, Elm Street Liquors has arrived on the scene to mix high-end lounging with a dive bar attitude. A 35-foot bar dominates the front room, while leather chairs and plush couches line the back. The music leans toward funky indie and techno beats, and exotic drinks are served in champagne flutes. Try the beer cocktails or the “Trust Fund” — a cognac-Cointreau concoction with a ginger-coated rim.
12 W. Elm

Funky Buddha Lounge - Featuring Moroccan décor and Victorian-style easy chairs, this combination lounge and upscale dance club in trendy Lincoln Park offers Latin, jazz, hip hop and house music provided by live bands and DJs. Think intimate jazz mixed with modern dance grooves — a totally unique experience.
728 W. Grand

Ghostbar - Located on the upper level of the trendy N9ne restaurant, this seductively-lit, ultra-chic lounge has a great atmosphere. A curved silver bar backlit with a green glow gives the room an eerie feel; the egg-shaped chairs add a touch of mod. Sit back and enjoy full bottle service or choose from a luscious selection of specialty cocktails. (The chocolate raspberry martini is out of this world!)
440 W. Randolph

The Grand Central - A retro sports bar combined with the elegance of a piano lounge, there’s nothing in Chicago quite like the Grand Central, which features white subway tiling, vintage detailing, a 29-inch plasma TV, DJs spinning nightly and an all-you-can-eat buffet.
950 W. Wrightwood

J Bar - Located in the sleek, ultra-happening James Hotel, J Bar offers deconstructed cocktails like a Ketel One martini with a vermouth-and-olive lollipop and the “Stoli Raz” served in a martini glass coated with a raspberry candy shell. Low-slung lounge seating, candlelit cocktail tables and plasma screens with video art set the swanky scene.
55 E. Ontario

The Motel Bar - Think of it as a hip motel bar without the motel. Gauzy curtains, orange vinyl booths, old-fashioned cocktails, a pool table and a jukebox all make the Motel Bar the perfect destination for fun, understated cool.
600 W. Chicago

Rockit Bar and Grill - Once occupied by a lamp factory, this happening nightspot in hip River North leads the traditional bar and grill into the 21st century. Exposed beams, brick walls, a 75-foot skylight and a cosy upstairs lounge all create an atmosphere that puts a new twist on an evening out.
22 W. Hubbard

Plan B Bar + Kitchen - Plan B offers something for everyone, from a low-key after-work destination to an energetic, feel-good late- night scene with great music. Led by principals Ryan Golden and Mark Perres, Plan B Bar + Kitchen offers a well-edited bar menu, straightforward beer selections and premium, reasonably-priced cocktails against a perfect blend of sexy rock, vintage hip-hop, old school and 80s classics by local DJs. With seasonal menu items and drink specials, along with the installation of three plasma screen TVs (at seated eye-level), Plan B should be the first choice for entertainment.
1635 N. Milwaukee