The Show Outside of the Show

What happens to America's third-largest city when over 100,000 people take over its downtown?

In addition to our FLOOD Festival Guide presented by Toyota C-HR—which is available for download now—FLOOD will be at all this year’s best festivals to provide you with firsthand reports from the scene.

The stories about Lollapalooza don’t start and end with the performances themselves. When an event of this magnitude hits a major city, many other smaller moments play out just beyond the festival gates—ones that the livestreams just can’t catch. But we’ve got you covered. Here are a few short stories about the infamy outside Lolla this year.

Rain falls on Lorde / photo by Carlo Cavaluzzi

Rolling in the Rain

When a severe thunderstorm evacuation cuts Lorde’s headlining set short, relatively calm streets nearby give way to a hellscape of muddied basketball jerseys and star-spangled trunks, clear ponchos over two-piece swimsuits, and careless pedestrians weaving between cars as though they were playing a game of Frogger.

At one intersection, rows of headlights catch a woman in a rainsoaked white tee and jeans waving her hand while she darts between street corners, stopping at the scene of a minor fender bender. She begins positioning herself a safe distance away from the two conversing motorists and quickly turns her back, sweeps the clumped hair away from her face and smiles as she pulls out her phone. The glare from an ‘L’ station, a mattress store, and the sidelined vehicles become the backdrop for a Snap story she begins narrating.

After a night that ended early, many others like her paced the streets, aimless and searching for any slice of action.

When Worlds Collide

With Lolla confined to an expansive downtown park along the city’s skyline, most average Chicagoans breeze through the weekend without ever once encountering the grounds or the tens of thousands it attracts. Of course, there are some exceptions.

For a short time on Saturday afternoon, the area around Lolla’s southernmost gate entrance becomes something of an rendezvous point for a meeting between “business as usual” Chicago and “here for the party” festivalgoers.

As the Chicago Bears Family Fest disperses from nearby Soldier Field, toddlers bounce in strollers and parents hold the hands of skipping kids—all clad in Bears jerseys—as they move down a parkway approaching the gate. In one instance, a silver-haired, beer-bellied gent with a baby on his hip passes by an approaching group that could’ve been cast for Mean Girls 3, led by a Kylie Jenner doppelgänger with contoured lips, an ivory crop top, and thick, swinging gold-hoop earrings.    

The pit of despair / photo by Brigid Gallagher

A Sneak-In Attempt Gets Derailed

For the very low price of free ninety-nine, anyone not wanting to shell out on a day wristband can post up along a grassy strip directly across from the Chicago Hilton. The trail boasts a side view of one concert stage, just close enough to clearly listen in on performances, catch a glimpse of the monitors, and see beach balls bouncing amidst a haze of smoke that lingers just above the crowd.

There’s just one (big) thing getting in the way. The short fence along the trail sits atop a wall descending 20 feet into an open yard for regional commuter-rail trains. But for one eager guy, there ain’t no valley low enough to keep him from Lolla.

Soon after 21 Savage launches into “Red Opps,” a tall, thin guy in a green shirt climbs over the fence, having found a way to scale down the wall. “He got down!” one of his friends shouts, as he lands on the gravel beneath him. Onlookers gather nearby as he sprints toward the train tracks in hopes of finding a path up to the other side, where all the fun awaits.

But before he can get across, someone inside the festival catches the attention of an officer. He bolts back and somehow manages to escape before three transit authority trucks arrive along the tracks.

On patrol / photo by Brigid Gallagher

They Did Battle with a Gate—and the Gate Won

Mere moments after the great green escape, an apparent flash mob steals the show. No choreographed dance moves were necessary, only running shoes and the gumption to lunge at a side gate en masse in an attempt to storm into Lolla for free.

A few dozen people rush the barrier and zoom past a couple of contracted security guards. For a short time, it looks like some of them have managed to pull it off. But they soon return, running as far away from the grounds as possible.

One guy stands in the middle of the trail while the stragglers sprint past, telling his friend why this attempt couldn’t have been any more foolish.

“So you jump across one gate, and there’s another one behind it that you can see,” he says, referencing a second gate covered in a green tarp. “And then there’s three more gates before you get to where some of the security guards are hanging out.”

“Smart move, bros,” he says as he slow claps, before sharing that he’s just gotten off shift from working the event. “I even saw one of the guards tackle a guy just now.”

“Yeah, I got him,” the guard says. “That’s the second time this has happened today…and they planned it on social media.”

The masses / photo by Brigid Gallagher

Called Out for Cutting a Wristband Sale

Although ticket exchange companies purchase and resell wristbands nearby, some end up taking matters into their own hands, pawning off their passes to anyone walking by.

One prospective buyer snags a $60 wristband offer outside an entrance, less than an hour before Chance the Rapper takes the Grant Park stage. As the transaction begins, another guy butts in with money in hand. “I got this,” the original buyer says, but the other bidder persists. “Nah, nah, I’m going to pay for it,” he responds.

A young lady outfitted with glitter-studded braids takes notice from a nearby bench and intervenes.

“How you just gonna cut into his sale like that?” she says, throwing him off.

“Mind your business. Why do you care so much? Is he your man or something?” he asks.

“He doesn’t have to be my man, though, but why are you trying to cut him?”

“You don’t know who you talking to. I’m from the West Side.”

“And I’m from Logan Square, so what?”

“I got a ton of money too,” he retorts, flashing bills from his pocket.

“I don’t care what you got…have a blessed day and have a blessed life!” she yells back, before he throws up two middle fingers in her face and stomps away.

CPD at (relative) rest / photo by Brigid Gallagher

Cop Comics

As another evening winds down, two traffic officers walk from the Travelodge back toward Michigan Avenue, with fluorescent green vests hanging over their arms. Both ladies seem to be preparing themselves for yet another crazed evening of festivalgoers swarming the streets as the last performances wrap.

“I’m getting too old for this. These boys all look like they’re eight,” one officer says, sharing a laugh before the shift begins.

Steps away, just outside the main entrance, five bored police officers on bikes pass the time while observing passersby. It’s quite clear they’re ready to go home.

“Damn these Lolla days,” one officer says, before the group quips about rowdy teenagers and shares the snarky nicknames they’ve given the festival.

“LaLaLoopy,” another officer retorts, twirling a finger in circles around her ear—but it’s the next wisecrack that sends the group doubling over in laughs.

“PPO-palooza!” an officer shouts, before moving away from his bike and jumping up and down with his hands in the air with a listless look on his face, offering his best impression of a wasted reveler.

Goodnight, Lolla / photo by Brigid Gallagher

A Trump-themed Float Tries to Steal the Show

As Arcade Fire closes out the weekend, another explosive musical display takes shape just north of the park.

A long float heads southbound on Michigan Avenue blaring Martha and the Vandellas’s signature hit “Dancing in the Street.” On the flatbed itself, white letters spelling T-R-U-M-P sit atop a hill, lit up like the Hollywood sign, with two American flags perched on each side.

Fortunately, it doesn’t make it down the avenue, which has been blocked off by garbage trucks to help make way for pedestrians emptying out from Grant Park. The float holds up traffic for a few minutes on Randolph Street before it gets diverted to the east. Angry motorists slam their horns to voice their annoyance and disapproval.

Yet the float persists for the rest of the evening and finds a way to reach the south end of Grant Park, greeting people as they board trains and buses home. The unwelcome display is something of a grounding figure, reacquainting everyone with the reality they’d managed to escape with hours of live music, if only for a weekend. FL


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