15 Killer Outfits For Day-Drinking

When temps can't go any higher and the sun lingers into the night, Chicagoans come out of the woodwork to enjoy summer like no one else. Sidewalks are dotted with maxi-dresses, espadrilles, and floppy hats — all those fun items stashed in the back of our closets, reserved only for these three precious months. And if there's one thing this city does right in the summer, it's nightlife. From rooftop lounges to sidewalk patios, the city is stocked with restaurants and bars serving inventive cuisine and summer cocktails, such as spiked snow cones and killer margaritas. They pretty much beg for shorter workdays, longer weekends, and — we admit — a little day-drinking.
It’s not that we’re saying we do summer better than other cities, it's that...no, we are — we're saying exactly that. And with fall quickly approaching, it’s time to enjoy these last few weeks while we have them. So, grab your gladiators and sunnies, and get yourself to one of these 15 must-try hot spots.
1 of 15
What happens when you serve slow-smoked, bone-in short rib with a sneakily strong, frozen bourbon cocktail with blackberry, lemon, and mint while blasting country music in the trendy River North neighborhood? A magical union of comfort food, kick-you-on-your-ass cocktails, and good-old-fashioned patriotism — a place where you can finally sport your Jessica Simpson-circa-Dukes of Hazzard cowboy boots without feeling like Jessica Simpson circa mother of two. The flag made of beer cans stationed over the bar doesn’t hurt, either. We’re not quite sure if it’s the eight-buck cluck-fried-chicken sandwich served up on a soft bun with — what else? — a mini red-white-and-blue flag stuck on top, the giddy-up fries topped with barbecue pork and melted cheddar cheese, or the live country acts that has the crowd filling this new honky-tonk spot every night, but either way, we’ll settle for the nice selection of wholesome, take-home-to-mama guys.

Bub City, 435 North Clark Street (between Hubbard & Illinois streets); 312-610-4200.

Clockwise from top left: girl. by Band of Outsiders Silk Pleated Drop-Waist Dress, $415, available at Saks Fifth Avenue; Bauble Bar Lucite Garden Drops, $28, available at Bauble Bar; Kate Spade Sailor's Knot Hinge Bangle, $78, available at Kate Spade; Dolce Vita Hartley Boot, $92.90, available at Dolce Vita.

Photo: Courtesy of Anjali Pinto.
2 of 15
This River North lounge-restaurant hybrid is known for its literary-inspired bohemian vibe, a menu of thoughtful gastropub fare, and sophisticated cocktails. Packed with vintage knickknacks, eclectic furniture finds, and bright, interesting artwork, it’s the perfect place to order your grandpa’s favorite cocktail — a Manhattan served up with two cherries — and wax poetic over the good ol’ days when literary fiction was still worth reading. And though the conversation might drift into territory a little less highbrow than the Hemingway types you envision at Hubbard Inn, don a flirty, black skirt and graphic-print sweater, and you’ll fit right in.

Hubbard Inn, 110 West Hubbard Street (between Clark & LaSalle streets); 312-222-1551.

Clockwise from top left: Benefit Ultra Plush Lip Gloss, $16, available at Benefit; McQ Alexander McQueen Swallow Print Sweatshirt, $325, available at MyTheresa; Michael Kors Rock Crystal Ring, $95, available at Neiman Marcus; Jeffrey Campbell Montana Boot, $189.95, available at Lori's; Theory Mini Skirt, $448, available at The Corner.

Photo: Courtesy of Hubbard Inn.
3 of 15
While the American classics prepared with locally sourced ingredients at this newly opened River North resto are good, what we’re crazy about is the interior. Elements of reclaimed wood are rustic without seeming pretentious, and the sculptural light fixtures up the design quotient just enough to feel modern. Inspired by the cuisine of cities spread across the Central time zone, it has everything from chicken-fried alligator to a Wisconsin-grilled-cheese sandwich. Don’t be fooled, though, the after-work crowd is still sporting plenty of suits, so ditch the bar garb for something a little more sophisticated like a tribal-print dress and bright clutch. We’re due for a second trip to keep navigating through the list of creative cocktails — the Alabama Slam with Southern Comfort, amaretto, slow gin, OJ , and bitters, admittedly, slowed us down.

Central Standard, 169 West Kinzie Street (between Wells & LaSalle streets); 312-527-9409.

Clockwise from top left: Rebecca Taylor Silk Floral Dress, $325, available at Rebecca Taylor; J.Crew Stone Mix Necklace, $135, available at J.Crew; Ramble Square Toe Sandals, $130, similar styles available at Topshop; Clare Vivier Fold Over Clutch, $185, available at Shopbop.

Photo: Courtesy of Cory Dewald.
4 of 15
This recently opened spot by Top Chef fan favorite Fabio Viviani and the guys behind the DineAmic Group (who brought us popular pubs such as Public House and Bull & Bear) fuses Italian flavors and recipes into American comfort dishes like short-rib ravioli and crispy brick chicken with Parmesan potatoes. The resto’s partners spent two weeks eating and drinking their way through Italy to glean inspiration for the concept, so now it’s time to test the fruits of their “labor” at this trendy spot. We’re digging the breezy vibe of these floral-print skinnies and peplum top to try the newly offered brunch menu on weekends, which makes us feel like we’re jet-setting to Lake Como. You never know, you might just catch the eye of a newly single George Clooney…well, a girl can dream.

Siena Tavern, 51 West Kinzie Street (between Clark & Dearborn streets); 312-595-1322.


Clockwise from top left: Joe's Jeans Palm Beach High Water Jeans, $80.25, available at Neiman Marcus; Madewell Peplum Tank, $68, available at Madewell; Dannijo Cody Necklace, $525, available at Shopbop; Raoul Red Britt Leather Clutch; Ann Taylor Shay T-Strap Leather Sandals, $79.99, available at Ann Taylor.

Photo: Courtesy of Anthony Tahlie.
5 of 15
Located in the Trump International Hotel & Tower, this sophisticated lounge boasts sweeping views of Chicago’s iconic architecture, including the Wrigley Building and Tribune Tower, and it’s a gorgeous lookout point to catch the Navy Pier fireworks during the summer. Bust out the big-girl heels and a geometric-print dress and feel like a high roller sitting in plush chairs, because if anyone knows the value of dressing up for a stiff drink during cocktail hour, it’s the Donald. And with a menu titled Liquid Kitchen, Rebar is sure to be up our alley — its mixology program emphasizes fresh juices, mixers, and fresh herbs and spices, and the cocktails pair perfectly with the sushi menu’s specialty maki rolls like the toasted lobster. Top it off with one of Rebar’s sweet “pops” — a passionfruit lolli with a dark-chocolate shell or banana-hazelnut push-up.

Rebar, 401 North Wabash Avenue (between Kinzie St. & Wacker Dr.); 312-588-8114.


Clockwise from top left: Tibi Multicolor Transit Dress, $450, available at Tibi; J.Crew Beaded Rose Necklace, $128, available at J.Crew; Rebecca Minkoff Craig Camera Bag, $195, available at Rebecca Minkoff; River Island White Ankle Strap Pointed Croc Wedges, $92, available at River Island;

Photo: Courtesy of Rebar.
6 of 15
With nearly a dozen restaurants under his belt, the unofficial “mayor of Chinatown” Tony Hu brings his authentic Chinese cuisine to River North at his new joint, Lao18. The interior boasts a more sleek and upscale vibe — golden antique birdcages hang over the booths and a brass swirl-shaped sculpture hangs above the dining room. Bright colors like this Kara Ross python clutch and print dress will pop against the room’s primarily neutral slate. The menu, however, is anything but neutral as crazy-spicy dishes like the Szechuan-peppercorn sole filet with chile relleno make trying the cocktails a must. Go for the Revival Shochu Smash, which is named for the ingredient shiso’s revitalization properties in Chinese medicine and is sure to cool any residual heat.

Lao 18, 18 West Hubbard Street (between Dearborn & State streets); 312-955-8018.

Clockwise from top left: Great Plains Women's J1AA9 Orchid Bloom Dress, $145, available at Coggles; Maison Martin Margiela II Ring, $385, available at The Corner; Plomo Coral Red Suede Braided Bootie, $296, available at Bona Drag; Vince Camuto Julia Crossbody Bag, $105.86, available at Nordstrom.

Photo: Courtesy of Jeff Schear.
7 of 15
There’s not much more we Chicagoans love in the summer than a hot rooftop lounge, and we always seem to be on the hunt for the next new one. This summer, we’re totally crushing on The dec, Ritz-Carlton Chicago’s new outdoor terrace, with its cool, blue-lit lounge seating and outdoor fire pit to warm up next to when the breeze off Lake Michigan hits in the early evening. Needless to say, it’s time to bring your A-game: a chic, ’70s-inspired jumpsuit, stilettos, and drop earrings. This is the Ritz, after all. Tucked away, high above Water Tower Place, this hidden spot is ideal for escaping summertime tourists shopping the Mag Mile. Let’s just try and keep it under wraps, okay?

The dec, 160 East Pearson Street (between Michigan Ave. & Mies van der Rohe Way); 312-266-1000.

Clockwise from left: Yves Saint Laurent Mascara Volume Effet Faux Cils Babydoll, $30, available at Sephora; 3.1 Phillip Lim Stretch Silk Twill Jumpsuit, $729, available at Harvey Nichols; Sophie Hulme Floral Envelope Clutch, $718, available at Matches; Tory Burch Clemens Drop Earring, $61.60, available at Tory Burch; Topshop Unique Hi Strappy Sandals, $230, available at Topshop.

Photo: Courtesy of Christian Horan.
8 of 15
We were already big fans of this cocktail lounge that opened last summer atop the Raffaello Hotel, but ever since Craig Schoettler (the former executive chef of Grant Achatz’s The Aviary) was named beverage director last fall, the place has seriously upped its chic factor. His inventive approach to cocktails is evident in his newest summer endeavor: Grey Goose vodka Moscow Mules served on draft from an outdoor lemonade stand. Keep it light with a Marni bag, strappy sandals, and printed romper topped with a cool fedora. And while we love the sexy interior with dim lighting and tufted-leather couches, Chicago’s few months of warm weather are all about taking advantage of Drumbar’s 1,500-square-foot, open-air terrace, which boasts views of Lake Michigan and the John Hancock Building.

Drumbar, 201 East Delaware Place (between Mies van der Rohe Way & Dewitt Place); 312-924-2531.

Clockwise from top left: Skaist Taylor Bird Print Romper, $610, available at Wantering; IIIBeCa West Broadway Satchel, $198, available at IIIBeCa; Monki Ulrike Sandal, $8, available at Monki; Goorin Bros Blue Notes Fedora, $140, available at Goorin Bros..

Photo: Courtesy of Timothy Hiatt.
9 of 15
Get ready for some serious people-watching at this Gold Coast mainstay. For years, Tavern on Rush has been a favorite of the see-and-be-seen crowd, and when its wraparound corner patio is open during warmer months, diners can expect plenty of worthwhile distractions — not to mention auto-ogling at the numerous Ferraris, Maseratis, and Porsches parked out front. Preppy, embroidered shorts, a denim top, and Ray-Bans say, “I just breezed over here for a martini in between browsing the sale at Barneys and getting a blowout.” Known for its classic cocktails and contemporary steakhouse fare, such as prime steaks, chops, and cold-water lobster tails, the menu features plenty of more-casual options, such as thin-crust, brick-oven pizzas and one of our favorite burgers in the city. And while there’s nothing better than a glass of Santa Margherita Pinot Grigio underneath the bright-red awnings, be warned: The 114-seat patio is reserved for full lunch and dinner service only.

Tavern on Rush, 1031 North Rush Street (between Bellevue Pl. & Elm St.); 312-664-9600.

Clockwise from top left: Mango Washed Effect Denim Shirt, $49.99, available at Mango; Gap Colorblock Canvas Tote, $40.45, available at Gap; J.Crew Ratti Regatta Short, $98, available at J.Crew; Sol Sana Ainslie Sandal, $67.99, available at Need Supply Co.; Ray-Ban Aviator Large Metal, $195, available at Ray-Ban.

Photo: Courtesy of Tavern on Rush.
10 of 15
Remember the days when long weeks of travel were segmented by stops in a warm inn where you could sidle up next to the bar for a strong whiskey? Well, no, not really, but now we can imagine, thanks to Logan Square’s Longman & Eagle. The modern take on an old Chicago neighborhood inn is one where we could definitely stay a while. It's retro-in-a-good way interior begs for a too-cool-to-care look of leather shorts, crossbody Marc Jacobs bag, and white T-strap sandals. With nearly 150 whiskeys to choose from, the selection is unanimously recognized as one of the best in the city. Thirty daily selects at $3 per shot means we get to sample to our hearts’ content, and the six chic rooms (the custom-designed furniture, local art, and exposed-brick details complete the mood) adjacent to the restaurant are available for overnight stay. Just sayin’.

Longman & Eagle, 2657 North Kedzie Avenue (between Schubert & Milwaukee avenues); 773-276-7110.

Clockwise from top left: Joe Fresh Leather School Bag, $99, available at Joe Fresh; Stella Forest Lightweight Sweater, $265, available at Les Pommettes; Pamela Love Dove Ring, $220, available at Otte; Jeffrey Campbell Melina Boot, $165, available at Need Supply Co.; Alexander Wang Cuffed Leather Shorts, $750, available at La Garçonne.

Photo: Courtesy of Clayton Hauck.
11 of 15
When the restaurateur behind this 50-seat cocktail bar is Matthias Merges, you know he’s going to kill it. The Charlie Trotter's vet hooked us with Yusho, his restaurant of Asian-inspired street food, and has lured us back again with Billy Sunday. The lounge boasts just the right amount of retro to not seem pretentious and serves impeccable cocktails. Each signature drink starts with a different spirit, so that no two taste alike, and we’re thinking even the Prohibition-era evangelist, who serves as the eponym for the bar, would be hard-pressed to resist washing down items like crispy pig ears and steak tartare without one of the celebrated cocktails.

Billy Sunday, 3143 West Logan Boulevard (between Kedzie Blvd. & Milwaukee Ave.); 773-661-2485.

Clockwise from top left: Adriano Goldschmied The Beau Slouchy Skinny in 15 Years Thrasher, $134.99, available at Zappos; Bauble Bar Iced Gold Lariat Necklace, $28, available at Bauble Bar; Zara Star Print Clutch Bag, $49.99, available at Zara; Chanel Rouge Coco Shine, $34, available at Nordstrom; Cole Haan Pelham Strap Wedge, $228, available at Cole Haan; Equipment Riley Cutout Washed-Silk Top, $295, available at Net-A-Porter.

Photo: Courtesy of Matthias Merges.
12 of 15
We waited a long, long time for brothers Michael (of Blackbird) and Patrick (of Signature Room) Sheerin to open Trenchermen last summer. Even now that Michael is moving on to new ventures, Trenchermen's luster is still going strong, thanks to a seasonal menu of filling foods with inventive twists. Don a few cool touches like worn-in skinnies, chunky-heel sandals, and a loose-fitting, silk tee — the better to sample the menu with — and you're set. After all, a "trencherman" is a hearty eater and drinker, and that's something we can definitely get on board with.

Trencherman, 2039 West North Avenue (between Hoyne & Damen avenues); 773-661-1540.

Clockwise from top left: Hudson Collin Skinny Youth Vintage Jeans; Rebecca Taylor Silk and Lace Tee, $265, available at Rebecca Taylor; Adia Kibur Antique Pendant Necklace, $30, available at Shopbop; Elizabeth and James Clair High Heel Sandals, $147.50, available at Shopbop.

Photo: Courtesy of Derek Richmond.
13 of 15
With one of the city’s It patios for afternoon cocktails that roll into late dinners, the wait at Big Star leaves something to be desired…but once you snag a seat, what comes next is another story. Thanks to executive chef Paul Kahan (that’s right, of Blackbird) and chef de cuisine Craig Svozil, this whiskey-, tequila-, and beer-focused venue is not your run-of-the-mill Mexican joint. While you can’t serve inventive tacos without an extensive tequila list and killer-strong margaritas, it’s the selection of bourbons and $3 daily whiskey shots that give this place the honky-tonk feel of a Texas bar. Grab a floral maxi, sunnies, and a little worn-in denim, and get moving, because Big Star fills up fast. Whiskey and tacos — who knew?

Big Star, 1531 North Damen Avenue (South of North Ave.); 773-235-4039.

Clockwise from top left: Lavender Brown Carwash Maxi Dress, $190, available at Couture Candy; rag & bone Jean Burney Tattered Denim Vest, $225, available at Intermix; Dolce Vita Fanta Sandal, $118.30, available at Dolce Vita; Pietro Alessandro Colorblock Convertible Handbag, $129, available at South Moon Under; ASOS Round Sunglasses With Metal Bridge, $20.36, available at ASOS.

Photo: Courtesy of Big Star.
14 of 15
It’s safe to say the secret is out about Nellcôte — flour milled in-house to create the perfect al-dente pasta and crispy-yet-doughy pizza crust, tasty small plates, and a still rosé that we can’t sip enough of this summer. And we haven’t even mentioned the chic crowd of Taylor Momsen types vying for a rock-star sighting (which isn’t far-fetched, given The Rolling Stones-inspired restaurant is the usual pick for musicians while in town, and Billy Corgan, Florence and the Machine, Kelly Clarkson, and Imagine Dragons have all been spotted there). But those in the know head to RM Champagne Salon, the hidden gem located directly behind Nellcôte, for a nightcap of Veuve Clicquot and mignardise. The easy-to-miss entrance is just around the corner, down a back alley lit by Christmas-tree-style lights leading to a Bohemian-chic patio and quaint interior with plenty of two-tops for a little tête-à-tête. Harness your inner Bianca Jagger with a maxi-dress and statement jewelry that’s the perfect balance of hippie and chic.

Nellcôte, 833 West Randolph Street (between Green & Peoria streets); 312-432-0500.

Clockwise from top left: Issa Embellished Silk-Chiffon Maxi Dress, $1,320, available at Net-A-Porter; Amrita Singh Azzurra Cuff, $100, available at Amrita Singh; Lauren Merkin Tatum Turquoise Raffia Clutch, $295, available at Lauren Merkin; Stuart Weitzman Strapback, $178, available at Stuart Weitzman.

Photo: Courtesy of Potluck Creative.
15 of 15
Among the many West Loop spots along the city’s unofficial restaurant row, Randolph Street's Embeya continues to top our list, thanks to the progressive Asian eats of executive chef Thai Dang. This summer, it debuts a spacious, new patio, flanking the restaurant along Jefferson Street, that's perfect for sporting a floral top, black skinnies, and a chunky, white cuff. With the mix of outdoor tables and lounge couches tucked underneath a gazebo-style pod, Embeya is calling our name. And beverage director Danielle Pizzutillo’s new cocktails are hard to resist — handcrafted snow cones in flavors like rum and cherry, or bourbon with falernum and citrus, as well as spiked sodas like kumquat and vodka.

Embeya, 564 West Randolph Street (between Jefferson & Clinton streets); 312-612-5640.

Clockwise from top left: Motel Galaxy High Waist Matte Skinny Pants, $50, available at Motel; Giambattista Valli Floral-Print Silk-Chiffon Top, $910, available at Net-A-Porter; Forever 21 Cutout Cuff; River Island Black and White Two Part Pointed Pumps, $38, available at River Island; BCBGMAXAZRIA Allie Whip-Stitch Satchel, $228, available at BCBGMAXAZRIA.

Photo: Courtesy of Joe Compan.

More from Chicago


R29 Original Series