Party on Like Rudolph With This Red Nose Punch
In this hotel lobby, you won’t find stale bagels and a computer from the ‘90s with a dial-up connection. You will find a ridiculously ornate, almost church-like frescoed ceiling, marble columns, and a sparkling little bar serving up $13.50 cocktails including chocolate mint mojitos and Manhattans made with Palmer House-batched bourbon. Order up some lobster rolls and Angus beef sliders and charge it to the Underhills.
One of the sexiest spots in the city for sipping $13 cocktails is this top-floor lounge at the Raffaello Hotel, where the laid-back sofa vibe of the indoor lounge is a mere prelude to the stunning outdoor lounge with primo views of the lake and Downtown. Opt for the whisky-packed Penicillin or bourbon-based House Cobbler served by one of Chicago’s top female bartenders, but skip the $11 plate of olives. Unless you’re really into olives.
While the exposed-brick and sofa aesthetic of the downstairs bar is beautiful in its own right (and often packed with beautiful people), the seductive charms of the upstairs bar is where Maude’s really takes things to the next level. The dark atmosphere and soft amber lighting are practically begging you to make a friend of the opposite sex. And if you make a fool of yourself trying, it’s too dark for anyone to really notice anyways.
For some, there is nothing more beautiful than a Polynesian girl in a grass skirt. For such people, there is Three Dots and a Dash -- the bar equivalent of the popular tropical male fantasy. Yes, there is bamboo. Yes, there are strange Polynesian sculptures and art. But the most beautiful thing in the place could in fact be the drinks, served in coconuts, giant clamshells and, of course, treasure chests pouring out with dry ice fog.
Named after the opulent French Riviera villa where The Rolling Stones recorded Exile on Main Street (quite possibly the greatest rock album of all time), the West Loop’s version of Nellcôte keeps the vibe alive with Stones-themed drinks like the Under My Thumb, Let It Bleed, and Wild Horses served beneath elegant chandeliers and marble columns. In other words, it’s like partying in a palace for rock & roll royalty (or West Loop accountants).
It doesn’t get much more beautiful than this in Chicago. But while the white tablecloths and chandeliers of the indoor space can be a little stuffy, the equally beautiful outdoor space keeps the vibe light and airy with the aid of cocktails like the bourbon- and prosecco-based Bourbon Monarchy, the whisky- and absinthe-backed Remember the Maine, and, of course, Champagnes that put that gas station bottle of Korbel from NYE to shame.
Barrelhouse Flat is an anomaly to the typical beautiful bar in that a) you don’t have to pay $13 for a cocktail and b) it’s open ‘till 4am, well past the point of looking beautiful for many of its patrons. Nevertheless, it remains a classy cocktail oasis in a sea of cookie-cutter college bars, with all the classics including mint juleps and whiskey sours plus more inventive offerings like the tequila- and ginger beer-based El Diablo and the Jimmie Roosevelt made with Cognac and sparkling wine.
There’s no denying the top-floor lounge of the newly revamped Chicago Athletic Association, Cindy’s, is a beautiful place. You’ve got a skylit restaurant. You’ve got a rooftop deck. You’ve got what just might be the best vodka tonic in the city. You’ve got a Shake Shack downstairs. But when it comes to sheer natural beauty, nothing tops the view overlooking Millennium Park and the lake.
There’s no doubt the modern cocktail emporium of the Aviary is a beautiful place. And it's doing things with cocktails that you’ve only imagined in your most hallucinatory of dreams. But what might be even more beautiful than grabbing a seat in Grant Achatz’s sleek den of cocktail reinvention is scoring a seat to its exclusive downstairs speakeasy The Office and losing yourself in its library-chic vibe.
With walls decked out with steel shutters from a Kentucky bourbon distillery and terrazzo flooring from the original Berkshire Hotel back in the 1920s, there are worse places to chill and wait for your room to be ready than the ACME Hotel’s Berkshire Room. Sip a Weston made with bourbon, pipe tobacco, and “coffee essence” or try your hand at a dealer’s choice cocktail where you choose the spirit, flavor profile, and glassware and let the bartender do the rest.
If you’re the type that finds distilling machinery easy on the eyes, you’re the type who will find the industrial-chic surroundings of CH Distillery a thing of beauty. Watch the inner workings of the brewery-style distillery equipment as you pump booze into your own system courtesy of cocktails like the gin- and egg white-infused The Baron Takes the Sea or more seasonal offerings like punch bowls and boozy snow cones. Also, the Wi-Fi password is “DrinkMore,” so you get the idea...
If you find yourself getting all hot and bothered in the Chase teller window, your arousal might prove uncontrollable at The Bedford, where you can sip drinks inside a renovated bank vault. But it’s not just imaginary stacks of Benjamins that’ll get your heart rate up. It’s cocktails like the Scotch and vermouth Monty Burns, massive bowls of tequila punch, and drinks ranging from $300 bottles of Dom Perignon to $4 cans of PBR. Tallboys, of course.
Hidden beneath Sumi Robata is the intimate 12-seat Charcoal Bar, dedicated to the fine art of Japanese cocktail making. Impress a date as you pull up a seat on black lounge sofas or, better yet, at the futuristic bar to watch the bartender hand-carve your ice sphere and drop it into drinks including the 12-year whiskey- and shochu-infused Mother of Dragons or the Red Wedding made with Jamaican rum and Swedish punch.
No list of beautiful bars is complete without the inclusion of a Downtown rooftop bar such as ROOF on theWit, which covers all the bases thanks to a stunning 27th-floor rooftop lounge open all year, DJs and, of course, runway models (the bar is converted into a runway during fashion shows). You can also get craft cocktails, punch bowls, Champagne, and pisco pitchers in addition to sushi rolls and duck confit bánh mì. So yeah, a little more classy than BW3.
1. Palmer House Hilton17 E Monroe St, Chicago
2. Drumbar201 E Delaware Pl, Chicago
3. Maude's Liquor Bar840 W Randolph, Chicago
4. Three Dots and a Dash435 N Clark St, Chicago
5. Nellcôte833 W Randolph, Chicago
6. RM Champagne Salon116 N Green St, Chicago
7. Barrelhouse Flat2624 N Lincoln Ave, Chicago
8. The Office At Aviary955 W Fulton Market, Chicago
9. The Berkshire Room15 E Ohio St, Chicago
10. CH Distillery564 W Randolph St, Chicago
11. The Bedford1612 W Division St, Chicago
12. Charcoal Bar702 N Wells St, Chicago
13. Roof on the Wit201 N State St, Chicago
14. Cindy's12 S Michigan Ave, Chicago
First opened in 1871, this downtown hotel has become a classic mainstay of the city, located within walking distance to numerous attractions like Millennium Park, Grant Park, and the Art Institute of Chicago. It features luxurious rooms and amenities like a fitness center, restaurants, bars, and a spa.
Not only is Drumbar one of the sexiest rooftop lounges in Chicago, the 18th-floor bar atop the Raffaello Hotel has a brag-worthy selection of whiskey, scotch, bourbon, and cognac. The sleek spot has a cozy den-meets-gentlemen's club decor with dark leather couches, wood-paneled walls, and a marble bar. During the summer, the seasonal outdoor patio makes it even more of an after-work drinking destination near the Magnificent Mile.
A second installment from the Gilt Bar folks, Maude's is a two-level gastro-tavern that feels like a lived-in Parisian dive, with mismatched chandeliers, candles in vintage jars, and weathered, "electric blue" metal chairs, fortunately the type of electri
Three Dots and a Dash is a tiki-themed speakeasy in the back of Bub City that's pouring out crazy tropical cocktails in vessels like glass skulls and treasure chests.
Nellcote was named after the mansion on the French Riviera in which The Rolling Stones recorded Exile on Main Street, and it bears all the trappings that you'd expect for a place connected to such fame and splendor. Beyond the fanciful decor, this restaurant features an eclectic menu ranging from pizza and pasta, to wood-grilled chicken and pork belly confit.
This secluded alleyway bar/restaurant in West Loop is a prime spot for sipping bubbly, slurping oysters, and devouring luxurious cheeses. The French-inspired menu is filled with sharable plates and classic brasserie mains like croque monsieur and steak frites. If sparkling wine isn't your thing, don't worry, the bar serves its fair share of craft beers and cocktails. RM's picture-perfect interior features chandeliers, a cozy fireplace, and white tablecloths, and the secluded outdoor patio is a prime spot during the warmer months.
This two-floor throwback cocktail bar in Lincoln Park churns out classic tipples like Sazeracs, Old Fashioneds and Manhattans alongside lesser-known drinks like the Jimmie Roosevelt, a blend of cognac, green chartreuse and Champagne. Choose from 60+ varieties of shaken or stirred drinks.
This classy speakeasy is located below The Aviary, and is only accessible by invitation, or booking a private party (up to 16 people). Prepare yourself for $20+ cocktails and creative small plates with a similarly decadent price tag.
Inside the Acme Hotel in River North, The Berkshire Room is an old-time cocktail lounge that harks back to when the hotel was called The Berkshire Hotel from the 1920s to 1950s. The drink selection puts a heavy emphasis on barrel-aged cocktails, but the real stunner is the Dealer's Choice, essentially an off-menu cocktail based on your choice of spirit, flavor profile, and glassware. The space is dark and cozy with black-and-white tiled floors and a long, glossy bar.
CH Distillery is Chicago's first distillery/cocktail bar, serving up house-made vodkas with carefully curated concoctions, as well as small plates from other renowned Chi-town eateries. The distillery makes vodka (distilled 40 times for ultimate purity!), rum, whiskey, and two kinds of gin, all in-house. The bar then pours them into inventive, Chicago-inspired craft cocktails such as the Rhymes With Orange, made with Serrano chili vodka, orange Curaçao, lime, and watermelon. The small plates eats include corned duck on black rye, and charcuterie from West Loop Salumi. Does the CH in CH Distillery stand for Chicago? No! No it does not. The CH stands for the periodic symbols for carbon and hydrogen, the fundamental components that make alcohol. And if you can remember that after you've had a few of these cocktails, you might be almost as impressive as the cocktails themselves.
Named for the Bedford, IN limestone that continues to comprise the exterior of the historic Home Bank & Trust building, TB's an 8000sqft den of dining and drinks that includes the bank's original vault room, which's lined with wall-to-wall lockboxes and other trinkets.
Charcoal Bar provides a unique Rising Sun-style cocktailing experience for a select 11 guests.
Do you like models, bottle service, and DJs? If so, theWit's rooftop lounge is for you. More than just a glitzy bar, the 27th-floor hotspot features a retractable roof (it's open year-round, after all), a 3D video-mapping wall, and a sleek bar that turns into a runway. The food and drink menu is equally fit for a glam squad, serving up flatbreads, seafood towers, fancy craft cocktails, and punch bowls.
Cindy’s is one of the most beautiful restaurants in the Loop with views of Millennium Park and Lake Michigan, but underneath its glass dome ceiling atop the Chicago Athletic Association Hotel it doesn’t simply rely on its looks. Cindy’s has a host of gifted bartenders who whip up unexpected “potions” like the Alsatian Rustbelt (made with Del Maguey Vida mezcal, Wolfberger Amer Fleur de Joie, lagunitas, and lime) that complement its upscale, seafood-forward menu. At brunch the egg dishes, like the cast iron-made quiche with chard, leeks, and gooey emmental, are buttery and light, and at dinner the shellfish platter and the grilled salmon with horseradish crème fraîche are both rich but pleasantly light ... but the late night fried cheese curds might be the sexiest thing on the menu.