For more than two decades, the Lollapalooza Music Festival has constantly been ranked as one of the top North American Music Festivals.

The three day music fest brings together a diverse line-up that includes the top alternative rock and hip-hop acts, the latest indie and EDM artistes, and living legends like Depeche Mode and Paul McCartney.

What began as a one-time farewell tour for Jane’s Addiction has grown into a four day festival with over 200,000 attendees per day, and international expansion into six different countries.

Just like Bonnaroo or Coachella, Lollapalooza is considered by many to be a bucket list music festival and an event that should be experienced at least once in a lifetime. Splurging on a once in a lifetime experience makes sense and a purchasing a VIP Lollapalooza Tickets is almost the ultimate splurge.

Only almost, because the ultimate Lollapalooza splurge is the purchase of a Lollapalooza Platinum pass that includes climate-controlled lounges, concierge service, and more.

Lollapalooza VIP tickets are far more attainable, but at nine times the price of a General Admission ticket is a Lollapalooza VIP ticket worth the cost?

Bombay Sapphire and Bacardi cocktails at the Lollapalooza VIP lounge

Lollapalooza VIP Lounge Day One

Lollapalooza opens their gates at 10:00 AM but the lines to enter the festival actually beginss to form hours before that; Luckily a Lollapalooza VIP ticket means that you can avoid spending hours in the line by using the Dedicated VIP Festival Entrance.

Getting into Lollapalooza before the crowd is definitely a plus.

The Lollapalooza VIP experience involves a specially curated menu featuring food that’s just as diverse as the artistes on the line-up. Food isn’t served until 11:00 AM, so there is an hour to get familiar with the various alcoholic beverages;
A mobile Jack Daniel’s Whiskey bar features their eponymous whisky mixed with Cola, Tennessee Fire served on the rocks, and the custom-made Lolla Lemonade; which was a mix of Jack Daniels Tennessee Honey, sweet tea with a splash of fresh lemon juice.

Access to unlimited Tennessee Whisky is great, but for the price of a Lollapalooza VIP Ticket, Gentleman Jack on the rocks would have been a nice touch.

Jack Daniel's Tennessee Whiskey at the Lollapalooza Music Festival in Chicago

Up next was a classy looking Bombay Sapphire booth serving sophisticated gin cocktails like the Peppered Peach Collins; a mix of gin, fresh lemon juice, iced tea and black pepper.There was also the classic Tom Collins cocktail for anyone who wanted a less aromatic drink.

Bombay Sappire classic in cocktails at the Lollapalooza Music Festival in Chicago

Bacardi ran the most popular bar in the Lolla Lounge, serving Mojitos with freshly muddled mint leaved and the classic Cuba Libre every few seconds.

Maestro Dobel Tequila made ‘black diamond margaritas’ with a rim of black salt in a lounge area designed to resemble a beach complete with black sand, beach chairs, and beach balls.

I stuck with Jack and Colas and Bacardi Cuba Libres for the entire first day of Lollapalooza,; mostly because they both came in cool souvenir cups and I was craving the simplicity of alcohol and cola.

Jack Daniel's and Coca-Cola

The Food Options in the Lolla Lounge are quite varied. The only downside is that the famous Lollapalooza Lobster Dog is nowhere to be seen. Since this is Chigaco, the perfect place to start is with some miniature slices of Lou Malnati’s cheese pizza at the Italian Booth.

The Italian booth also served toasted cheese ravioli garnished with Parmesan cheese and served on a bed of marinara sauce, miniature meatball subs doused in marinara sauce, and breadsticks stuffed with mozzarella cheese served with ranch dip.

Meatball Marinana Sub, Deep Dish Pizza, and Mozarella Stuffed Breadstick at Lollapalooza

After snacking for almost an hour straight, I left the VIP Lolla Lounge to actually see some performances.

Amazing acts are always carefully selected to open the festival since they set the tone for the entire weekend. COASTS was no exception.
I’d become familiar with their music over the last few years and their live performance was full of energy.

Major Music Festivals with Star-studded line-ups are always filled with disappointing clashes that make seeing all your favorite artistes almost impossible.

Luckily, I only wanted to see three acts that were all following each other on the main stage; Cold War Kids, Alabama Shakes and Paul McCartney. Finding a spot near the front of the Bud Light Stage is a Herculean task that involves standing stage side for over seven hours, especially when the headliner is a former member of The Beatles.

Paul McCartney at Lollapalooza

Knowing that I would be away from the luxuries of the Lolla Lounge for the rest of the day, it was time to enjoy a few more cocktails, eat some slices of deep dish pizza, and prepare for some once in a lifetime live music!

Paul McCartney at Lollapalooza

Lollapalooza VIP Lounge Day Two

I began the second day of Lollapalooza with a tequila sunrise followed by a bottle of Daily Greens vegetable and fruit juice since that combo seemed like a balanced choice for a liquid breakfast at a music festival.

I relaxed in the Lolla Lounge waiting for food to be ready, luckily the folks at Maestro Dobel tequila were more than willing to keep the margaritas flowing before lunch.

Having started the day with tequila, I decided to keep it Mexican themed by only eating food from the booth labelled “Taco”. The food on offer included grilled steak fajitas with cilantro and mole, beef barbacoa tamales dipped in green chili, and elote on a stick seasoned with Parmesan cheese and dried peppers.

Tacos and Tamales at Lollapalooza

I went stage side to catch Catfish and the Bottlemen who I’d seen for the first time at the Governors Ball Music Festival the year before.

Catfish and the Bottlemen at Lollapalooza

I stayed inside the VIP Lolla Lounge to see Django Django. The view from the lounge is vast and allows you to see the band along with the entire festival crowd and the Chicago skyline in the distance.

The acoustics actually travel well but being able to sit with a drink in hand was the best part of listening to music in the Lolla Lounge.

Choosing a headline act was a much tougher call than Friday since pop crooner Sam Smith and rock legends Metallica were playing on opposite ends of Grant Park.

I skipped both headliners and decided to relax in the lounge instead of trying to get a good spot near the front of either of the main stages.

I had some more Maestro Dobel cocktails and miniature Chicago-style hot dogs while listening to Kid Cudi’s performance in the background.

I ended the day by watching BANKS and G-Eazy on one of the festivals smaller stage. Thanks to the golf kart shuttles that transport Lollapalooza VIP Ticket holders between the two main stages; I did manage to catch a little bit of both Saturday Headliners although for Metallica, it was just their encore of “Enter Sandman”.

Lollapalooza Perry's Stage

Lollapalooza VIP Lounge Day Three

The third day of the festival is the day that I most appreciated having a Lollapalooza VIP ticket.
The combination of a scorching sun and the general fatigue from partying for two days straight, made a seat in the shaded Lolla lounge the best place to be.

I watched the Chicago based Twin Peaks, and British Indie band the Wombats from the lounge that day.
The Lolla Lemonade made with Tennessee Honey and sweet tea was just what I needed that day. It was sweet and tangy with a boost from the caffeine.

Jack Daniel's Bar at Lollapalooza

I also downed loads of Vita Coco coconut water. I actually had enough coconut water left over from Lollapalooza to last me an entire week!

The weather was amazing when I left the VIP Lolla Lounge to catch some of the opening acts of the day, The Wombats followed by local band Twin Peaks.

The Wombats at Lollapalooza

I was unaware of an impending storm, but some of the Jack Daniel’s bartenders brought me up to speed and gave me a free branded poncho. When the evacuation of Grant Park did eventually happen, the Lollapalooza VIP sections were among the first areas in the festival to be cleared.

I headed back to the hotel, got some rest and came back recharged for an energy packed performance from Gogol Bordello.

Eugene Hütz of Gogol Bordello

With my schedule now thrown off, and knowing that I just wanted to see TV on the Radio and Florence and the Machine again I decided to try some more Lollapalooza VIP food that I might have missed.

Mini Chicago-style and jumbo pretzels with a cheddar cheese sauce dip was not something that I would typically go for, but it ended up being the ideal carefree finger food to snack on.

Jumbo Pretzel and Mini Chicago-style Hot Dog

The weather never fully cleared and there was always some clouds in the sky, but that lead to the occasional flash of lightning as Florence and the Machine closed the show. I left the music festival as the sounds of an extended Bassnectar set pulsed in the distance and people swarmed the streets after three incredible days of music.