Alright, so I guess it’s that time of year again when out-of-towners hoard to Chicago to get a ‘real’ music experience at one of the biggest ‘festivals’ the country has to offer, all stuffed into the context of a humid midwest summer. As if three days of mud-soaked teenagers in affronting native-american garb wasn’t enough to fill the pockets of downtown aldermen, we’re quickly reminded of the manifest destiny that is the last week of July. Yes, Lollapalooza is back bigger than ever and packing more of a punch than ever before. While the lineup is undeniably filled with plenty for everyone, it can intimidate even the most seasoned festival vet with feelings of anxiety over where to go next, what ‘moment’ is more worth missing and just which headliner from the last five years of Lolla to relive once again this year, something that’s becoming an annual tradition for those of us that stop by somewhat regularly. However, it appears the extra day of stages opened up routing and availability for organizers to throw a larger arm around local acts, a move that is a welcome furtherance of the Chicago Renaissance we’ve been experiencing here for the last five years or so. Without further ado though, I give you my gameplan for getting through the 2016 edition of Lollapalooza the right way.

Day 1

For those of you either without weekday responsibility or with enough of it to say screw it mid-day on a Thursday, then by all means take that long lunch break straight to Jazz Cartier who should prove to be the first true breath of life at the top-end of the crowded day one lineup. Dude has a live show and accompanying singles to turn up even the most tame, neon-clad college kid home from break, wondering why he’s standing over them, walking on their hands. Leaving that physical cup of coffee, my move would be to stroll by the Petrillo Bandshell to catch a couple songs of the always-entertaining Hiatus Kayote before settling in for the second half of Mr. Carmack’s set, continuing a sort of hot-cold juxtaposition of energy from one set to the next, easing into perfectly-suited Yeasayer set before getting back into the thick of it with what should be an inspired Danny Brown performance.

Ending at 5:00 once again at the Bandshell, that slot gives you just enough time to right your fanny pack, tighten your shoelaces and get a slight stretch in before going all the way up for Towkio’s debut Lollapalooza performance right in the middle of the day at 5:15 on The Pepsi Stage for what should be a really cool new chapter in the hometown act and member of SaveMoney. After drying off from that sweat-fest, I’d pop over to the never-disappointing A/V performance from Excision, a perfect warm-up to dive back into another Chicago mainstay with trap legends Flosstradamus before ending the night with a couple tracks from J. Cole’s 2014 Forest Hills Drive. Congratulations, you made it through day one and only really moved between two stages. Minor movement, optimal experience and you didn’t even have to watch Kehlani try to keep up with her backup dancers. You’ve made it through the appetizer and are sitting pretty for the main course.

12:50-1:30 - Jazz Cartier - Pepsi Stage

2:00-3:00 - Hiatus Kaiyote - Petrillo Bandshell

2:30-3:15 - Mr. Carmack - Perry's

3:30-4:30 - Yeasayer - Lakeshore

4:00-5:00 - Danny Brown - Petrillo Bandshell

5:15-6:00 - Towkio - Pepsi Stage

7:00-8:15 - Excision - Perry's

8:30-9:45 - Flosstradamus - Perry's

8:30-10 - J. Cole

Day 2

One of the coolest things I can say about Lollapalooza the last couple of years has been the festival’s willingness to tap into the musical renaissance that we have happening here locally. Following suit with Pitchfork and North Coast who have increasingly tapped local talent for their stages, this year around boasts some of the best names from around the city’s streets. One of those is Saba, who takes the Pepsi Stage at 12:50 to kick off our day two and should be looking to close the chapter on his 2014 ComfortZone release, using the big stage to help do so with what should be a rousing early day performance. After that I’d lay low and try to catch a couple bottles of water or free cocktails however you can before continuing on with the local talent as SaveMoney's second third act of the weekend, Joey Purp makes a surprise  debut on the Perry's Stage in place of Skepta, sidelined by visa issues. The set, one of a flurry from Purp lately, should prove to be a huge benchmark in his career. After that you would be well-served to catch Lettuce and Cherub back-to-back for some real good vibes from a pair of collaborators with fellow local ProbCause, who introduced me to their eclectic dance sounds.

After that? It’s right back to our wheelhouse of the Bud Light-Petrillo Bandshell and Pepsi stage for an onslaught of hip-hop as Mac Miller, Future and A$AP Ferg should put even the most casual of rap fans into some sort of frenzy. Then, take all that energy and focus it into a paper cylinder to ease into the smooth, willowy vibes of Radiohead who will almost assuredly be playing songs from their latest project, A Moon Shaped Pool. Whew. Two days in and we’re only halfway there. Friday has plenty of after parties, local DJ Oreo is actually hosting three days of post-event celebrations around town, but if you’re here for the real triumph of getting to all four days you’ll need all the strength you can muster.

12:50 - Saba - Pepsi Stage

2:30-3:15 - Joey Purp - Perry's

3:45-4:45 -  Lettuce - Petrillo Bandshell

4:45-5:45 - Cherub - Bud Light Stage

5:45-6:45 - Mac Miller - Petrillo Bandshell

6:45-7:45 - Future - Bud Light Stage

7:45-8:30 - A$AP Ferg - Pepsi Stage

8:00-10:00 - Radiohead - Samsung Stage

Day 3

Alright let’s be real. After two days of heat, booze and whatever else, you’re going to want a nice night of sleep and a big brunch, or at least a decent couple hours and a breakfast burrito. Whatever works for you, don’t worry because you’ll have some time before things really get moving Saturday. Me? I’d arrive just before three to see Tory Lanez who never fails to impress and should be a similar experience to Jazz Cartier on Thursday. At his show at Reggie’s last winter dude literally walked on the crowds hands to different parts of the venue, performing seamlessly the whole time, we’ll have to see what he has in store for the fest crowd.

After that, I’d peruse whatever access points you have for food and drink before heading into Big Grams, the confluence of pop/dance duo Phantogram and rapper Big Boi. After getting a few songs there, I’d head into the soul-inducing back-to-back of Leon Bridges at 4:45 on the Bud Light stage and Jack Garratt at 5:15 on the Pepsi stage. His girlfriend is from here and word is he plays harder, wouldn’t really know as I’ve only seen him here, so cheers! After that, dive back into 2012 with the trio of Two Door Cinema Club, Big Gigantic and Grimes which will have you tearing up at Pitchfork’s heyday. Get out of all of those asap though and make sure you have a good spot at the Pepsi stage where our very own Vic Mensa will at long last make his Lollapalooza headlining debut, six years removed from nearly dying while sneaking into the event as a high school student. Talk about storylines.

2:50-3:30 - Tory Lanez - Pepsi Stage 

4:15-5:15 - Big Grams - Samsung Stage

4:45-5:15 - Leon Bridges - Bud Light Stage

5:15-6:00 - Jack Garratt - Pepsi Stage

6:45-7:45 - Two Door Cinema Club - Bud Light Stage

7:00-8:15 - Big Gigantic - Perry's

7:30-8:30 - Grimes - Lakeshore

9:00-10:00 - Vic Mensa - Pepsi Stage

Day 4

If you really made it this far, then do it all and get there early because Lolla did you dirty and front-loaded the final day of this Music Marathon. Why escew sleep on the last day before getting back into the real world of afternoons spent in offices and classrooms? Because Smino’s playing the opening set, and Smino doesn’t disappoint. The St. Louis native has made quite the name since arriving in the Chi and should put his stamp on a very successful twelve months with his debut Lolla set. Don’t go anywhere though, following him is another talented local in Sir The Baptist, who parlayed a series of talented singles into a recent signing with Atlantic and subsequent dates at Bonnaroo and here where he also makes his first appearance. D.C. native and close collaborator with Chance The Rapper and The Social Experiment, D.R.A.M. should have one of the most fun sets of the weekend in the middle of the day on Sunday, once again right at the Bud Light stage, once again preluding yet another Chicago talent in Louis The Child who have blown up over the last year through their distinct and up-tempo dance stylings. From there, it’s smooth sailing with some fairly easy listening in Bryson Tiller and Snakehips before taking in the IDC attitude of Vince Staples, who endeared himself to the city late last year when he voiced his distaste for Spike Lee’s ‘Chiraq’ movie at a show at the Bottom Lounge. With all that in the bag, there’s really only one way to close out such a weekend and that’s by taking in the sounds of the one and only LCD Soundsystem, which might just be for the final time. With all that, slap yourself on the back; you did it. Now get your dirty ass back to work, life isn’t a festival once Monday comes.  

12:00-12:30 - Smino - Pepsi Stage

12:50-1:30 - Sir The Baptist - Pepsi Stage

4:00-4:45 - Louis The Child - Pepsi Stage

5:45-6:45 - Bryson Tiller - Petrillo Bandshell

6:30-7:15 - Snakehips - Pepsi Stage

7:45-8:30 - Vince Staples - Pepsi Stage

8:30-10:00 - LCD Soundsystem - Samsung Stage