Nightlife
Meet the Nightlife Leaders Behind Red Bull’s Battle of The Captains
What happened when the best of Chicago threw the ultimate celebration on the river.
With all due respect to, well…anywhere else, Chicago nightlife is one of the best on the planet. A Midwest melting pot, the city’s bars, restaurants and clubs benefit from everything the region has to offer: A desire to take care of each other while still giving each other space. And abundant public transit options and ride shares to make sure that everyone gets home safely. And of course, a thriving culinary scene. Which is great because it’s easy to hit several locations in the same night, but a city big enough that there’s a ton of variety. (Cozy bar, club vibes, or somewhere in between? Yeah, they've got that.) It’s nearly impossible to go out in the Windy City and not find something to love. Besides, as the colder season approaches, where else would we go other than indoors to a welcoming local spot?
All that is why, during the final days of summer, Red Bull brought six of the city’s finest restaurants, bars, and clubs together for an ultimate showdown for Red Bull Battle of the Captains. Part competition, part celebration, Deuce's Major League Bar, Whispers, Joy District, D.S. Tequila Company, and PB&J: Pizza Beer and Jukebox were each given a boat a, a DJ (Avi Sic, Dani Deahl, Don Parra, Billa Beats, Will Galvan, and Apollo XO laid down beats for their respective teams) and one simple goal: to create the ultimate floating party.
After an hour-and-a-half ride down the Chicago River, everyone joined up for an after party DJed by Layla Benitez and Autograf. It was there that Whispers at Oak Street was crown as the winner. (We’ll be back next year to clinch another winning title!” said owner Jenna Alia. “I’m just honestly super surprised! We're competing with the big players!”) But the true champions are anyone who visits any of these Chicago nightlife landmarks.
Larger than life
© Chris Hershman / Red Bull Content Pool
Deuce's Major League Bar
Located in the heart of Wrigleyville, Deuce's Major League Bar takes inspiration from its surroundings. Which, in a nod to the nearby Wrigley Field, you’re able to snack on ballpark favorites like giant pretzels (which seasonal dipping sauce), wings, and even Cubby-blue milkshakes with gummy bears, gumballs, sprinkles, and rock candy. But from the Miami-reminiscent upstairs fountain where patrons are encouraged to take a dip while enjoying their drinks, to their holiday pop-ups (You’ll know Halloween and Christmas is coming), they’ve made it their business to never be just one thing.
“We started doing the pop-ups three to four years ago,” explains general manager Jasper Robinson (who had his entire team wear pink during the Battle of the Captains in honor of his daughter’s favorite color). “Instagram has just become so popular, and everyone wants to take pictures…it just makes sense for us in order to provide not just our like party atmosphere, but to actually provide experience.”
But it isn’t just Santa Claus and skeletons that have found a home at Deuce’s. Although Chicago is home to the finest sports teams in the world, you’re welcome whether your loyalties lie on the home or visiting side.
“We definitely cater to the different times of the year, and different vibes,” says Robinson. “[There’s this] huge LA Dodger fan club, they flew in like 300 or 400 people and all came to Deuce’s before the Dodgers/Cub game. We were [a] Dodgers bar, essentially, for that day.”
Battle of the Captains
© Chris Hershman / Red Bull Content Pool
Whispers
As one of Chicago’s only beach-side restaurants, Whispers’ off-Michigan Avenue location can feel like a well-kept secret. But after three years in business, owner Jenna Alia is still excited to share the beauty of her club and restaurant.
“You see the water and you see the city, and it’s a perfect beach slash metropolitan vibe,” she says. “Sometimes I take my kayak out on the water, and I look back at the beach, and I get chills.”
Covered in flowers, the summer vacation vibe at Whispers runs deep—something Alia only encourages by adding Crayola-colored drinks, “motivating” her staff with the occasional Super Soaker surprise attack, and staging well-attended beach parties. (“Everyone here is always happy,” she notes.) It’s not just the salmon ceviche that has guests returning, but the overall vibe.
“We’ve been having parties and we were bringing out some great DJs,” Alia says of the events that she throws in her beachside lounge area. “We’ve had five or six hundred people come out, and they're just dancing on the beach, and they're drinking and living their best lives. Good vibes all around. I had two bars at my restaurant, and now we've got four just to accommodate the amount of people that come in for those parties…It’s fantastic. We've got our DJ and the gazebo going hard and then all these people and their swimsuits. One time the water even came into like the dance floor!”
Kitty Kat
© Red Bull
Joy District
Joy District is an old-school, multi-level nightclub. If you’re just looking to dance it out or hanging out with friends on the sleek, Instagram-friendly roof while enjoying the view, they’ve got you covered. (Keep your ears open: Demi Lovato, Ludacris, Travis Scott, and Louis the Child have all taken a turn behind the decks.)
But located behind the walls of the River North venue is life beyond bottle service. Get your late-night snacks at their in-house bistro Parlay, where you can nibble on burgers, pizza, mac and cheese, and all manner of carb-lover snacks. Bonus: with their lavish brunches (Saturdays and Sundays, 11am-3pm), they’ve got your entire weekend covered.
D.S. Tequila Company
© Red Bull
D.S. Tequila Company
As the name implies, Boystown’s D.S. Tequila Company is the place to be for anyone who appreciates the agave spirit—which gives it an edge during events like Pride Week and Taco Fest.
“Two weekends ago...I looked at our credit card receipts and 70% of the people were from out of state that we're visiting that weekend,” says Director of operations, Dusty Carpenter, noting that they’re also popular with locals. “Boystown is a very knit community, so a lot of people bounce around the same places all the time.”
But even if you’re aiming dinner instead of drinks, D.S. Tequila Company has you covered with the founders’ other passion, Tex Mex style tacos and a Noah’s Ark worth of burger options. (Carpenter recommends the Barnyard, which true to its name includes a beef patty, applewood smoked bacon, BBQ brisket, fried egg, and provolone.)
“At the end of the day we take a lot of much pride in our food, and the atmosphere we create for people, from our burgers and tacos, to our DJs,” says Carpenter. “We just try to make sure no matter what time of day you come into our business; you're always having a great experience.”
DJing on the river
© Red Bull
Blind Barber
With a line out the door nearly every night, Fulton Market’s Blind Barber isn’t a secret—even if guests enter through a functional barbershop, just like classic speakeasies. Ultimately, as co-owner Rob Wilce explains, their popularity as a seemingly well-kept secret comes down to understanding what clients want. He should know—he was one of the first clients of Blind Barber New York, and such a fan, he jumped to open a Chicago branch of the barber shop/speak easy.
He speaks highly of the staff that got them through a lean year and a half. After all, it’s their hard work that helps set the tone for guests’ nights out.
“We provide good drinks, the best service and we make sure there's music,” he says. “That's it. There’s the gimmick of walking to the barbershop, but it's actually not a gimmick that that barbershop is purely functional—so I am a firm believer in keeping it simple….Every night is like a house party. You do not walk down any stairs but we'll have people say like, ‘Hey, I gotta go upstairs really quick!’ when they're talking about literally just going out to the street. It’s really funny…. There’s a lot of inhibitions that get lost once you pass that threshold. So, it is kind of a wild place on the weekends.”
PB&J
© Red Bull
PB&J: Pizza Beer and Jukebox
PB&J co-owner Dougie Stylz loves his regulars, and people who come by looking for a taste of the true Chicago flavor. (Yes, they have pizza, and yes it’s delicious.) But there’s a special VIP section of the menu, dedicated to everyone’s favorite four-legged friends. Dogs are more than welcome in the West Loop restaurant. And if you invite them, they will come.
“There was one point where I was tossing a ball around,” Stylz jokes of a recent service. “We have water bowls all over the place, so I think that if you're a dog owner, sometimes you don't want to leave them at home when you're going to grab a bite to eat or grab a drink or something like that. So hey, bring your dogs!”
But even if you’re just there to watch the animal show or local sports on one of their many big screens, you’ll find something to like, whether it’s their fried chicken, loaded peanut butter and jelly sandwiches (yeah—it’s more than just a clever restaurant name), or the freedom to just chill out.
Stylz compares his restaurant to a clubhouse, where every should feel like they belong, noting that he brought the same energy to the Battle of the Captains boat ride. “ I love the social aspect of it all, I love conversing with people I love making people happy and stuff like that so that's just something that I've always tend to veer to in my life.”