And we back, and we back, and we back…for yet another year of Lollapalooza. I haven’t missed a single day of the festival since it settled in Chicago back in 2005, so 2019 will mark my 15th year in a row of this madness in Grant Park. No, I’m not sure when I’ll finally decide to scale back and start skipping days or the festival entirely. Yes, I’ve slowly become older than most of the people who attend Lollapalooza these days. But the combination of age and experience leads to wisdom, which is something I’m happy to share with anyone planning to spend time at the festival this upcoming week/weekend.
The most basic advice I can give is to know your limits and practice rigorous self-care whether you’re in Grant Park for one day or all four. Drink lots of water (more than you want/need to), wear sunscreen and bug spray, and don’t be afraid to find a spot and sit down for a bit. The number of people I see collapse due to exhaustion, dehydration, or too much alcohol/drugs every year just makes me shake my head. Wear comfortable shoes (NOT flip flops). Avoid bringing a bag or purse if you can, because there are separate security lines at the entrance for bags vs. no bags and I’ll give you one guess as to which one moves at least 3x faster than the other. If you absolutely have to bring a bag, make sure you’re aware of the Allowed and Prohibited Items list before packing it. Also be very mindful of the bag’s size, shape, and number of pockets because there are restrictions on those things too. These might seem like a lot of things to remember, but the good news is that most of them are common sense anyway. Just be smart about it, and you should be fine.
But what about the music? Navigating sets from 180+ artists over four days isn’t easy by any stretch of the imagination, and the best advice I can give you for scheduling is to map out your day in advance and avoid going from one end of the park to the other too often. The walk end-to-end through Grant Park takes about 15 minutes wading through clusters of people, and you’ll exhaust yourself quickly by doing it more than 2-3 times per day. If you’re facing a difficult time slot conflict between two or more artists, you’d be best off just picking the one at the stage closest to where you are at that very moment. Simple enough! Not familiar with enough artists to fill your schedule for the day? Let me try to help with a list of five performances you shouldn’t miss on each day of the festival. Here we go:
The first day of the 2019 Pitchfork Music Festival, all anybody could seemingly talk about was the heat. Chicago has been placed under an “Excessive Heat Warning” through Saturday evening, with temperatures reaching into the mid-90s though the “real feel” was just a touch over 100 degrees. So yes, it was hot. Everybody was sweating. Not much could be done about it, though some people took it upon themselves to find ways to keep cool. Fans, both paper and mini portable electric ones, were being used by many. Others brought mist bottles. Some simply felt they were wearing too much, and stripped down to the barest of essentials without resorting to outright nudity. The festival organizers were kind enough to offer up as much free water as you could drink, complete with giant ice tubs packed with bottled water free of charge, as well as water fountains in multiple areas of Union Park. At one point I spotted two large buckets filled with ice and a sign on them that simply said “DUNK”. A few brave souls just went right ahead and plunged their whole heads into them. There were also a few cooling buses available so people could have a seat in some air conditioning if they really needed it. Every time I walked past them they looked to be about half full. 
Now feels like a good time to cover some of the extra “things to do” at this year’s Pitchfork Music Festival that don’t revolve around standing in front of a stage and watching an artist play their songs. Obviously there are food and drink tents where you can get all kinds of different delicious things. If you’re a fan of limited edition craft beer, you might want to check out the Goose Island booth, where they’ll be offering Wit Awake, a collaboration with the band Parquet Courts that will be sold exclusively at the fest. All proceeds from those beer sales will go to the Freedom for Immigrants charity. Other spots you may want to explore in Union Park include the Flatstock poster fair, where artists showcase and sell various concert posters they’ve designed. There’s the CHIRP Record Fair, where you can find a whole lot of limited edition LPs for sale. If you’re bringing young children under 10 with you there’s also a Kids Zone featuring some fun distractions. And new for this year, Pitchfork Radio will be broadcasting live from the festival grounds. You’ll be able to watch some special live performances, DJ sets and interviews with artists on the lineup, and a few other things. Check out the 
Welcome to the start of another 
