The Definitive Guide to Chicago's Best Hotel Bars


The Definitive Guide to Chicago's Best Hotel Bars
The Definitive Guide to Chicago's Best Hotel Bars

Courtesy of Cindy’s at the Chicago Athletic Association
Courtesy of Cindy’s at the Chicago Athletic Association

Nothing against your corner bar and its sweet-ass Buffalo wings, but sometimes you’re in need of an entirely alternative experience. Chicago's hotel cocktail lounges are a different breed of bar -- clandestine, classy, historical, fewer shot skis -- and lapping up the lap of luxury isn't just for out-of-towners. Take in sweeping views of the skyline when it’s patio weather and slink around in the sleek decor with Prohibition-era quirks when it's, well, the other six months of the year. Consider upgrading your typical drinking, and possibly sleeping, environs for an evening in one of the city's 11 most nightcap-worthy hotels.

Cindy’s at the Chicago Athletic Association


One of the best new bars of 2015, the crown jewel of the recently renovated Chicago Athletic Association has the best view of Millennium Park AND the best drink named after an elephant that refused to leave a CAA party in the 1900s (The Hesitant Elephant). If you needed more, there’s Maker’s Mark pecan pie, Moody Tongue Caramelized Chocolate Churro Baltic Porter on draft, and late-night eats like poutine and cast-iron chilaquiles to make quick work of on communal picnic tables.

Courtesy of J. Parker

J. Parker

Lincoln Park

The Hotel Lincoln’s 13th-floor oasis provides the perfect escape from the cookie-cutter Downtown hotel scene thanks to magnificent (yes, we said magnificent) Lake Michigan views and an always-happening scene of attractive, buttoned-up ladies and gents. Join the cool kids with small plates from chef Paul Virant, including shrimp ceviche and mini burgers paired with cocktails like the pisco-based “In” Crowd (get it?), or bust the corporate credit card on $950 magnum bottles of Dom Perignon brut. Either way, you win.

Courtesy of Drumbar



On the 18th floor of the Raffaello Hotel, you’ll find one of the sexiest rooms in all of Chicago where dark woods and marble get you in the mood to dive into a comprehensive cocktail menu from one of Chicago’s top female bartenders. Whether you’re hitting up old classics like the Walk a Tightrope (made with rye whiskey and Goose Island sour blackberry rye beer) or new creations like the Candy Cigarette (including pisco, cream, coconut, and egg white), you’re pretty much guaranteed to stumble upon your new favorite drink. Or get plenty buzzed trying.

Flickr/Dan Dickinson

Pump Room

Gold Coast

The fabled Pump Room has been reinvented for the modern era at this swanky outpost of the PUBLIC Chicago where anyone who’s anyone hangs out to see and be seen (what, you’ve never been?) Settle into the Frank Sinatra booth in the ‘30s/’40s supper club-style dining room to unpack heavy-hitting eats like Maine lobster, filet mignon, and suckling pit confit or chat up hotties at the bar over a Passion Chili (with rye, passion fruit chili, and ginger ale) cocktail or the Scotch- and crème de cacao-based Queens Boulevard. Which we’re pretty sure Vinny Chase drinks.

Courtesy of I/O Urban Roofscape

IO Urban Roofscape

River North

It’s the largest indoor/outdoor “roofscape” in the city. What the hell is a roofscape, you ask? Well, it’s pretty much everything this place excels at: retractable roof, video wall, and a well-dressed, good-looking crowd dancing to the DJ under trippy club lights. For eats, there’s lamb lollichops and squash risotto. For drinks, there’s pitchers of white sangria and Deschutes Fresh Squeezed.

Courtesy of The Bar at The Peninsula

The Bar at The Peninsula

River North

The name may be understated, but The Bar is anything but. Unless your ordinary bar produces a dimly lit environment of sexy red walls, tall leather bar stools, and a roaring fireplace (because what the hell good is a fireplace if it isn’t roaring?) While best known for its martinis and rare whiskeys, drinks like the Hemingway daiquiri and White Whiskey Fizz (with grapefruit, maple syrup, and egg white) are no slouches either. The “smart casual” dress code applies to the bar bites as well, with mini Kobe burgers and sushi rolls getting you in the mood to mingle. Or not, it’s cool either way.

Courtesy of Vertigo Sky Lounge

Vertigo Sky Lounge

River North

In winter, the 26th floor of the Dana Hotel is most well known as the location of the city’s only (but totally necessary) indoor/outdoor rooftop ice bar. The rest of the year, it’s known as one of the biggest party spots in the hotel bar scene thanks to DJs spinning house, top 40, and live remixes amidst party accessories that may or may not include an outdoor fire pit, buckets of beer, and bottles of Cristal. If you’re one of those people who only does shots via ice luge (and why wouldn’t you be?), this is the clearly the place for you.

Courtesy of ROOF on theWit

ROOF on theWit


If you’re looking to pick up models in Chicago, you should probably hit up a bar named a “model’s choice” by Elle magazine. In addition to live runway shows, this equally visually stunning space features a retractable roof, 3D video-mapping wall, and several sleek spaces for skyline-view make-out sessions. Before swapping spit, however, one would be wise to indulge in eats like jerk chicken flatbreads and seafood towers paired with cocktails like the whiskey-based Bridgeport and vodka-heavy Sex on the Roof.

Flickr/Tobi Mattingly

Lobby Bar at Palmer House Hilton


One of Chicago’s most ridiculously ornate bars, where church-like frescoed ceilings and high-rising marble columns surround a sparkling little bar serving up chocolate chip mojitos and treetini martinis that plant a tree in the Brazilian rainforest every time you order one. (See, we knew you were environmentally conscious.) If you can’t make it to church on Sunday, this is a perfectly acceptable alternative.

Courtesy of Berkshire Room

Berkshire Room

River North

For those of you who can’t make up your goddam mind already, you’re lucky there is such a thing as the dealer’s choice cocktail. You pick your spirit, flavor profile, and glassware, and they do the rest at the ACME Hotel’s pretension-free temple of booze. No judgments: just a welcome respite from the typical wallet-gouging hotel bar scene thanks to beers like $4 Hamm’s and $3 Rhinelander paired with duck wings, bacon Reubens, and soft pretzel bites with beer cheese.

Freehand Chicago

The Broken Shaker

River North

Parked in the new upscale hostel (or “poshtel”) The Freehand, The Broken Shaker does everything a little bit differently. First, there’s the space decked out with octopus art and basement décor, with a laid-back house-party vibe thanks to DJs spinning old-school soul vinyl as travelers play Jenga on couches. Then there are drinks like the Trailer Park Smash (featuring bourbon topped with Miller High Life) and eats like pork al pastor skewers and seared Spanish octopus. Oh, and you don’t get bottle service here, you get punch service.

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Jay Gentile is a Thrillist contributor and he always checks to see if there's punch service first before booking a hotel room. Follow him: @innerviewmag.

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1. Chicago Athletic Association Hotel 12 S Michigan Ave, Chicago, IL 60603 (Loop)

Following a 2015 renovation, this historical building transformed into a boutique hotel with several food and drink options, including a patio-equipped Shake Shack and a rooftop restaurant with views of Millennium Park. The epic game room has bocce and shuffleboard courts, a pool table, and foosball, while the restaurant, Cherry Circle Room, serves a beef-centric menu and tableside cocktails.

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2. J. Parker 1816 N Clark St, Chicago, IL 60614 (Lincoln Park)

This rooftop bar atop the Hotel Lincoln features an impressive cocktail list, views of the park/lake shore/skyline, and small bites so good you'll hang around for a dangerously long time--no big deal.

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3. Drumbar 201 E Delaware Pl, Chicago, IL 60611 (Gold Coast)

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.

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4. Pump Room 1301 N State Pkwy, Chicago, IL 60610 (Gold Coast)

Reinvented for the modern era at the Gold Coast's swanky Public Hotel, the fabled Pump Room is one of the best hotel bars AND most romantic spots in Chicago. The best seat in the house is the glamorous Frank Sinatra booth in the '30s/'40s supper club-style dining room, and your waiter will surely give you a history lesson of the iconic people who've sat at the same table. The food and drink taste like old-school glamour -- think Maine lobster, filet mignon, and classy cocktails like the Scotch- and crème de cacao-based Queens Boulevard.

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5. IO Urban Roofscape 127 W Huron St, Chicago, IL 60654 (River North)

This seriously sleek rooftop spot is perfect for our 100 days of Summer. A lounge with swanky drinks and serious eats, this is the place to be when the weather's nice.

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6. The Bar at The Peninsula 108 E Superior St, Chicago, IL 60611 (Gold Coast)

This secluded Gold Coast bar (located in The Peninsula Hotel) has a fireplace, great drinks, and bar bites like mini Kobe burgers and sushi.

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7. Vertigo Sky Lounge 2 W Erie St, Chicago, IL 60654 (Gold Coast)

On the 26th floor of the Dana Hotel, this rooftop lounge is one of the best party spots in the Chicago hotel bar scene. In the winter, Vertigo turns into an indoor/outdoor ice bar where you can do necessary winter drinking activities like take shots on an ice luge. The rest of the year, it returns to its ultra-luxe penthouse vibe with DJs, bottles of Cristal, buckets of beer, and an outdoor fire pit.

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8. Roof on the Wit 201 N State St, Chicago, IL 60601 (Loop)

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.

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9. Palmer House Hilton 17 E Monroe St, Chicago, IL 60603 (Loop)

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.

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10. The Berkshire Room 15 E Ohio St, Chicago, IL 60611 (River North)

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.

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11. Broken Shaker 19 E Ohio St, Chicago, IL 60611 (River North)

An outpost of the fabled Miami hotspot, The Broken Shaker in Chicago is located at the upscale hostel (yes, hostel), The Freehand. The bar has a laid-back house party vibe with vinyl-spinning DJs, back-to-back rounds of Jenga, and cozy couches. Bottle service is traded for punch service and unique cocktails like the Trailer Park Smash (bourbon topped with Miller High Life) color the menu.