There’s a lot to love in Chicago, a fact we at Playboy have known well for almost 60 years—Si Non Oscillas, Noli Tintinnare, right? But it’s been a while since we’ve knocked around these parts, and with everything settled in the West for the summer, we’re riding east into the rising sun for an all-nighter soundtracked by the curators of the now legendary Lollapalooza. Any Chi-town native will tell you that come festival time, the city is engulfed in a veritable sea of festival-goers, off-site shows and after-parties that reaches its crescendo on Saturday night. It can be easy to forget that it’s just a music festival and not a three-day federal holiday running August 2-4.BEFORE THE FESTIVAL 1 P.M. - PUBLIC Chicago
Launched in 2011 as a hybrid luxury-economy guinea pig, PUBLIC Chicago is one of the few boutiques that walks the line between style and value with a semblance of balance. Under the leadership of Studio 54 ringleader Ian Schrager, PUBLIC offers high-end amenities (sky-view private terraces and the Pump Room restaurant/bar, hipper than most clubs anywhere) that won’t break the bank. Plus, with their inspired four P.M. checkout, you’ll have ample time to regain consciousness after rolling back in 16 hours from now. Photo courtesy of PUBLIC Hotel.4 P.M. - Masa Azul
Sometimes you go somewhere to drink tequila. Other times, you do that and wind up learning something. The keeners at Masa Azul have agave down and they want you to know about it. As if their comprehensive list of tequila and mezcal wasn’t enough, they also offer a small selection of sotol and bacanora, the increasingly rare and slightly more exotic cousins of the better-known agavaceae-based liquors. Order from their Flight Menu to sample the entire family, but be sure to keep your feet earthbound with our fave: tacos laden with braised pork, pickled onion and habanero salsa—perfect to rouse the senses before heading to the festival. Photo courtesy of Masa Azul.@ THE FESTIVAL
6 P.M. - The National
After striking emotionally damaged gold yet again with their latest, Trouble Will Find Me, and completing a hat trick of brilliant albums like so few other buzz bands have ever done, The National are making a victory lap of the festival circuit. Don’t miss their heartbreaking and darkly funny brand of festival-ready anthems. Photo courtesy of Brennan Schnell on Flickr.7:15 P.M. -Azealia Banks
It’s hard at times to see the songs behind the musician when she spends so much time launching expletive-loaded feuds on Twitter. But Banks’ breakout, “212,” is still a killer and her output since then has only cemented the promise of her long-delayed debut full-length in our minds. If nothing else, check in for the Brooklyn bombshell’s signature cadence and flesh-baring costumes. Photo courtesy of rpttp on Flickr.
**Editor's note: Citing a throat infection as the cause, Azealia Banks has since cancelled her appearance at Lollapalooza. We're bummed, too, but if you let *it get you down, won't nobody be to blamebut** yourself*********. In lieu of Banks, check out HAIM (playing in the same slot, conveniently), a troupe of California babes doing their best to* channel the Pretenders, as best displayed in their latest excellent buzz single, "The Wire."**8:45 P.M. -Death Grips
Get weird with the only band to exist at the nexus of punk, hip-hop and electronic music; they’ve opened for Bjork and are signed to the label headed by the guy who discovered Avril Lavigne. Curious associations aside, the band’s experimental records have earned bewildered-but-positive reviews, and vocalist Stefan Burnett is a force of nature whose live performance you don’t so much witness as survive. Photo courtesy of libertinus on Flickr.AFTER THE FESTIVAL 11 P.M. - Kendrick Lamar @ Aragon
You’ll be hard-pressed to gain access to the hottest after-festival show in Chicago, but the rewards for perseverance will be rich. Kendrick Lamar’s sound is as warm as the L.A. weather he reps so well, his lyrics uncommonly literary. The sound might go down easy—and fuel the best party of the night—but the labyrinthine subtext will have your mind wandering long after the crowd clears. Photo courtesy of nrk-p3 on Flickr.2 A.M. - Pat Mahoney DJ Set @ Smart Bar
With LCD Soundsystem peacefully departed and James Murphy off brewing coffee somewhere, if the closest you can get to touching the sound of silver is a DJ set from former LCD drummer Pat Mahoney (on the Saturday of Lollapalooza weekend, at one of the best after-hours in Chicago), you poor, unfortunate soul, just dance yrself clean. Mahoney’s current gig drumming for Lolla-players Hot Chip guarantees buzz-y guest appearances, and the man responsible for that much groove is almost certainly the only one capable of keeping you on your feet until the sun comes up. Photo courtesy of crowdstrudel on Flickr.
Header photo courtesy of Jareed on Flickr.