We here at InsideHook love a good hotel bar.
Patronized by passers-through and stoppers-by, they’re full of infinite possibility.
Now, two schools of thought prevail on how to make good on these thoroughly sexy spaces: Meet someone. Or bring someone.
We tend to opt for the latter option. Because if you stop and think about it, the hotel bar — with all of its unknown charms — make for the perfect venue for a date night. Below, nine of our favorites to do just that.
The Destination: Broken Shaker at the Freehand Chicago
The Vibe: One part hipster. One part tropical grandma kitsch. All part hostel. Think mahogany accents, colorful tile and mismatched tapestries, all in a dimly lit setting.
But Why Here? Broken Shaker provides a carefree ambiance in the heart of bustling River North. Not to mention the original Miami locale is one of the world’s 50 best bars. But that doesn’t mean they take themselves too seriously, an argument that can be made by cocktail handles like “Side Piece” and “Becky With the Good Hair.”
The Destination: Sable Kitchen & Bar at Hotel Palomar
The Vibe: Classic hotel atmosphere with elegant touches from end to end. If you’re looking for a kind of chic the older set can appreciate, this is your place.
But Why Here? One of Chicago’s original essential cocktail bars, Sable was a cool hotel bar before hotel bars were cool. And we can actually say it’s the cocktails that keep us coming back. The bar’s newly revamped menu features tipples grouped by different train lines, with each line serving a different compulsion. Going for something modern? Hop on the Metropolitan Line. Spirit-forward? That’s the Brown Line. Whatever you choose, Sable provides a cozy atmosphere to enjoy a stiff cocktail at the bar.
The Destination: Baptiste & Bottle at the Conrad Hotel
The Vibe: Located on the 20th floor of the Conrad, this newcomer offers city views overlooking Michigan Ave. and Streeterville. The hotel itself is the epitome of swank, and trust it's got a bar to match.
But Why Here? In a word: bourbon. Try the show-stopping A Curtsey and a Bow — a tableside-made cocktail featuring Basil Hayden's eight-year bourbon with orgeat, absinthe, and a dramatic helping of tonka bean fog. If bourbon isn't your thing, you can still find solace in plenty of wine and beer options, though whiskey lovers can buy a bottle and store the extras in a locker at no charge.
The Destination: The Game Room at the Chicago Athletic Association Hotel
The Vibe: Handsome as all get out. A place for all walks of life to gather, with amateur gamblers and pool sharks thrown in for good measure. Open to all on the second floor of the engrossingly beautiful Chicago Athletic Association Hotel.
But Why Here? The Game Room is simple, good fun, and so is its drink list. Wines by the glass include “Big” or “Little” red and white wine, eight cocktails curated by Paul McGee including a house bottled option, and a simple selection of draft and bottled beers. Work up an appetite for tacos, burgers and fries while trying your hand at bocce, shuffleboard, billiards and other tabletop games.
The Destination: Up & Up at The Robey
The Vibe: The Robey is Wicker Park’s shiny new toy, a boutique hotel that recently opened at the famed six corners. The triangular building is home to multiple places for imbibing, but it’s Up & Up that provides the best scenery.
But Why Here? Located on the 13th floor of The Robey, Up & Up successfully combines elements of old and new. The indoor and outdoor spaces feature Art Deco design coupled with modern and retro touches including white marble tables and angular furniture. Best part of the space? The view from the wrap-around terrace, presenting a new and unrivaled view looking south to the Loop.
The Destination: The J. Parker at Hotel Lincoln
The Vibe: Lincoln Park meets River North at this bar towering atop Hotel Lincoln. You've got your indoor section, but it’s the outdoor space on the south side that is the main attraction. Relax in a lounge chair or sit at a high top while taking in views of North Avenue beach and the Chicago skyline.
But Why Here? While some rooftop bars come with an heir of pretentiousness, J. Parker has a relaxed vibe where people come to hang, enjoy a drink and then see where the night takes them. The drink list is refreshingly simple. Keep your eyes peeled for a summer cocktail menu based on destination locations around the globe.
The Destination: Vol. 39 at the Gray Hotel
The Vibe: The ultimate gentleman's library with just the right amount of space to kick back and unwind. While The Gray is a relative newcomer to Chicago’s hotel scene, it’s keeping up with the pack.
But Why Here? Vol. 39 is not just some lobby bar. It’s as rich with history as it is with sophistication. Tall bookshelves line one side of the intimate space, housing vintage encyclopedias uncovered during the building’s renovation. Vol. 39 seeks to impress with rare wines and spirits, a caviar program, and a cocktail menu blending old and new, much like the Gray itself.
The Destination: Drumbar at the Raffaello Hotel
The Vibe: Located on the 18th floor of the Raffaello Hotel, Drumbar has held its own since its 2012 opening. Each space in the bar provides a different experience, so it's a good choice whether you’re in the mood for whiskey neat at the bar or al fresco.
But Why Here? The indoor bar provides a dark and intimate escape with rich leather booths and a cozy fireplace. Tucked away in another corner is a bright window-lined nook filled with green furniture, in stylish contrast against the black and white tile. Still, the outdoor spaces are Drumbar’s best assets. The ever-evolving cocktail list currently features #NetflixandChill beverages, all named after TV shows, including the Narcos with Tanqueray, Scotch, elderflower, lime cordial and egg white.
The Destination: LH Rooftop at LondonHouse
The Vibe: Champagne toasts and easily one of the most exclusive views in the city. Every element of the hotel effectively balances classic architectural elements with modern touches.
But Why Here? LH Rooftop includes three separate venues, each offering its own vibe and the next level more posh than the previous. Floor 21 provides a relaxed atmosphere with crushed velvet furniture and classic American cocktails and dishes. Meanwhile, floor 22 boasts the expansive LH terrace with its picturesque views overlooking the Chicago River. For a more exclusive experience, reserve the Cupola at the very top of LondonHouse, where nothing is too over-the-top.