Fashion Plates: What to Wear For 29 Nights Out In Chicago
We know the drill—it's 6 p.m. on a Saturday night, and you have nothing to wear…and no idea where you're going. Thankfully, we've got you. We're sharing our inside scoop on Chicago's best places for late-night revelry. But, because we love you, we felt compelled to take it one step further. That's right, we're giving you 29 spots that guarantee a fabulous evening, plus all the outfits you'll need to show up looking like one of the (cooler) regulars.
Very soon, you'll be overlooking the Wrigley Building from a plush chair in Trump's sexy lounge Rebar, chatting about the notes in a Sonoma Valley Pinot, taste-testing craft beers with a tattoo-sleeved hipster, sucking down refreshingly sweet margaritas with girlfriends, and sipping bourbon with a scruffy, Liev Schreiber-look-alike. The best part? There are more than enough spots on this list to ensure your Friday, Saturday, and (let's get real), Thursday nights are fully booked for the next few months!

Sexy Hotel Lounges
Rebar
With a name like Trump, it's pretty much guaranteed that the ambiance will be luxe, the drinks will be strong, and the real estate will be prime. Located on the mezzanine level of Trump International Hotel & Tower, Rebar is the perfect place to up the ante in a hot dress and stilettos — we're talking contemporary décor and wall-to-ceiling windows (with some seriously covetable views of the city), plus plenty of fine Italian suits at the bar. Grab a few girlfriends and order the Magic Winter Punchbowl, a take on traditional German glühwein.
Rebar, 401 North Wabash Avenue (between Kinzie Street and Wacker Drive); 312-644-0900.
Drumbar
And you thought rooftops were just for summer! Well, think again, because atop Raffaello Hotel, Drumbar’s sexy interior of tufted leather couches and warm dark wood paneling, is the perfect place to get cozy over an inspired cocktail menu. For colder nights, enjoy Tea Time with a few girlfriends — we suggest the Black & Red, a warm libation of red wine, Hennessy Black, cinnamon sticks, lemon sour, cardamom, nutmeg and orange served in a glass teapot.
Drumbar, 201 East Delaware Place (between Mies Van Der Rohe Way and Dewitt Place); 312-924-2531.
ROOF on theWit
We remember when ROOF on theWit hotel opened a few years ago in the Loop — the line of stilettos and miniskirts was down Lake Street — and we admit to wondering if its popularity would subside. But, that was before we went inside the 7,000-square-foot 27th floor lounge that literally oozes sex appeal. Lounge seating indoors is complemented by a retractable glass enclosure covering the outdoor patio, where bar stools line a long table and fireplace centerpiece. Snag a few of these seats with your girlfriends and be certain, the cocktails will come shortly thereafter.
ROOF, 201 North State Street (at Lake Street); 312-239-9501.
J. Parker
It’s probably too chilly to enjoy the stunning views of downtown and Lincoln Park from this perch above HotelLincoln, so duck inside and warm up with a classic cocktail: Mixologist Erin Hayes’ fall menu includes a variety of Kentucky Bourbon Trail-inspired libations like a Manhattan and Old Fashioned. Move on to the menu of small plates, overseen by chef Paul Virant from Perennial Virant on the first floor of the hotel. We like the sweet potato beignets and seared scallops with lemon butter and arugula.
J. Parker, 1816 North Clark Street (at Lincoln Avenue); 312-254-4747.
Vertigo
On the 26th floor of the Dana Hotel & Spa, Vertigo Sky Lounge is one of those spots you hit up to kick off a night that starts exactly as it begins: With plenty of dancing. The indoor/outdoor rooftop hosts live DJs nightly — plus, grab your faux fur coat and brave the elements for Vertigo’s annual December fire and ice winter patio returns.
Vertigo Sky Lounge, 2 West Erie Street (Between Dearborn and State streets); 312-202-6060.
Donna Karan Crepe-Jersey Dress, $1,995, available at Net-A-Porter; Vince Camuto Onyx French Clutch, $168, available at Vince Camuto; Alexis Bittar Swarovski Crystal Accented Orbiting Drop Earrings, $195, available at Saks Fifth Avenue; American Apparel Basic Leather Belt, $15, available at American Apparel; French75 Suede Stilettos, $125, available at Whistles.
Photo: Courtesy of Rebar
Very soon, you'll be overlooking the Wrigley Building from a plush chair in Trump's sexy lounge Rebar, chatting about the notes in a Sonoma Valley Pinot, taste-testing craft beers with a tattoo-sleeved hipster, sucking down refreshingly sweet margaritas with girlfriends, and sipping bourbon with a scruffy, Liev Schreiber-look-alike. The best part? There are more than enough spots on this list to ensure your Friday, Saturday, and (let's get real), Thursday nights are fully booked for the next few months!

Sexy Hotel Lounges
Rebar
With a name like Trump, it's pretty much guaranteed that the ambiance will be luxe, the drinks will be strong, and the real estate will be prime. Located on the mezzanine level of Trump International Hotel & Tower, Rebar is the perfect place to up the ante in a hot dress and stilettos — we're talking contemporary décor and wall-to-ceiling windows (with some seriously covetable views of the city), plus plenty of fine Italian suits at the bar. Grab a few girlfriends and order the Magic Winter Punchbowl, a take on traditional German glühwein.
Rebar, 401 North Wabash Avenue (between Kinzie Street and Wacker Drive); 312-644-0900.
Drumbar
And you thought rooftops were just for summer! Well, think again, because atop Raffaello Hotel, Drumbar’s sexy interior of tufted leather couches and warm dark wood paneling, is the perfect place to get cozy over an inspired cocktail menu. For colder nights, enjoy Tea Time with a few girlfriends — we suggest the Black & Red, a warm libation of red wine, Hennessy Black, cinnamon sticks, lemon sour, cardamom, nutmeg and orange served in a glass teapot.
Drumbar, 201 East Delaware Place (between Mies Van Der Rohe Way and Dewitt Place); 312-924-2531.
ROOF on theWit
We remember when ROOF on theWit hotel opened a few years ago in the Loop — the line of stilettos and miniskirts was down Lake Street — and we admit to wondering if its popularity would subside. But, that was before we went inside the 7,000-square-foot 27th floor lounge that literally oozes sex appeal. Lounge seating indoors is complemented by a retractable glass enclosure covering the outdoor patio, where bar stools line a long table and fireplace centerpiece. Snag a few of these seats with your girlfriends and be certain, the cocktails will come shortly thereafter.
ROOF, 201 North State Street (at Lake Street); 312-239-9501.
J. Parker
It’s probably too chilly to enjoy the stunning views of downtown and Lincoln Park from this perch above HotelLincoln, so duck inside and warm up with a classic cocktail: Mixologist Erin Hayes’ fall menu includes a variety of Kentucky Bourbon Trail-inspired libations like a Manhattan and Old Fashioned. Move on to the menu of small plates, overseen by chef Paul Virant from Perennial Virant on the first floor of the hotel. We like the sweet potato beignets and seared scallops with lemon butter and arugula.
J. Parker, 1816 North Clark Street (at Lincoln Avenue); 312-254-4747.
Vertigo
On the 26th floor of the Dana Hotel & Spa, Vertigo Sky Lounge is one of those spots you hit up to kick off a night that starts exactly as it begins: With plenty of dancing. The indoor/outdoor rooftop hosts live DJs nightly — plus, grab your faux fur coat and brave the elements for Vertigo’s annual December fire and ice winter patio returns.
Vertigo Sky Lounge, 2 West Erie Street (Between Dearborn and State streets); 312-202-6060.
Donna Karan Crepe-Jersey Dress, $1,995, available at Net-A-Porter; Vince Camuto Onyx French Clutch, $168, available at Vince Camuto; Alexis Bittar Swarovski Crystal Accented Orbiting Drop Earrings, $195, available at Saks Fifth Avenue; American Apparel Basic Leather Belt, $15, available at American Apparel; French75 Suede Stilettos, $125, available at Whistles.
Photo: Courtesy of Rebar
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