Cocktails/Wine Bars » Chicago, IL

Cocktails/Wine Bars in Chicago, IL

Chicago, with it's breathtaking skyline and picturesque views, has hundreds of spots to sip your drink of choice. From charming, intimate wine bars to high-energy clubs, Chicago has the bar for you.
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Chicago's most unique wine bar specializes in organic, inventive food offerings to compliment their impressive wine list. With dishes like whole roasted squab in a red wine reduction, the executive chef at Telegraph makes a point to create dishes that match the wine selection perfectly. This Logan Square locale exclusively features wine from small, family-owned European producers who craft their wine as naturally as possible, which adds to this bar's intrigue. The extensive wine list features 20+ glass pours and covers vintage, recent and mature wines. Planning a fun night out with the girls? Call ahead to try and reserve the 12-seat chef's table.

The Violet Hour

This iconic Chicago cocktail bar is located in the artsy, edgy Wicker Party neighborhood.  The Violet Hour does not accept reservations, so unless you plan to come early, you're in for a bit of a wait. With impressive cocktail ingredients like chartreuses, raw egg and root beer bitters, The Violet Hour is a must visit. They take their establishment seriously, as evident by their playful list of "house rules". An experience at The Violet Hour is often compared to a "trip down the rabbit hole" a la Alice and Wonderland. No cellphones are allowed in the lounge and whatever you do, do not order an O-Bomb!


Located in the charming Roscoe Village neighborhood, Volo is a boutique wine bar and restaurant with an urban flair. Volo has dozens of small plates, artisan cheeses and desserts to nibble on between sips of wine. In the warmer Chicago weather, Volo has patio seating with people watching that can't be beat. They offer sidewalk cafe seating and a charming backyard garden patio. Want less than a bottle, more than a glass? Order one of the 30 wines by the mini carafe, the equivalent of a third of a bottle. Here's another tip: hit up Volo on Mondays when they have half-price bottles.

Fion Wine & Spirits

Fion Wine & Spirits, dubbed Lincoln Park's most intimate and coziest place to have a drink, is a neighborhood bar beloved by the locals. Fion has a warm ambiance with soft, low lighting and a welcoming vibe. It's the perfect place to grab a cocktail with a girlfriend before dinner or to savor a handcrafted drink with your man on date night. While their wine list is impressive, try one of their signature cocktails using local, fresh ingredients. Bartenders at Fion are known for their inventive use of spirits and expansive knowledge of wine. Ask them for a recommendation - they won't steer you wrong!

The Bluebird

Situated in the hip and trendy Bucktown neighborhood of Chicago, The Bluebird is a craft beer and wine bar that is a local favorite. Billed as a "wine bar meets ale house meets bistro meets neighborhood watering hole", The Bluebird truly has something for everyone. The warm decor is inviting, the rustic touches abundant. One such example? The wood on the wall was repurposed from an old barn, the rich pine flooring restored from a small Illinois schoolhouse. Take heed: The Bluebird is a popular bar and doesn't accept reservations so be prepared for a bit of a wait.