All The Pros And Cons of Lollapalooza in Chicago

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Article Summary

  • The main pros of Lollapalooza are great music lineup, more bands than nearly any other festival, great food from throughout Chicago, and the public transportation allows you to stay anywhere in Chicago for Lollapalooza
  • The main cons of Lollapalooza are it is expensive, the Chicago summer can be brutal weather wise, drunk teenagers

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So many music festivals, so little time…and money. If we all had unlimited capital I’m sure we would attend Lollapalooza and every music festival under the sun. However, we don’t have unlimited capital, at least I know I don’t. Life is about making hard decisions on what is worth your precious money. This article goes over all the reasons you should attend Lollapalooza as well as the things about Lollapalooza that are less enjoyable. Read it, digest it, and decide for yourself if the pros outweigh the cons for you. Let’s get the bad stuff out of the way first and start with the negative aspects of Lollapalooza.

Con #1 of Lollapalooza – It is expensive

Lollapalooza is a big investment, mostly between the tickets and the accommodations. The wristbands last year climbed to $335 for a four-day general admission pass, which is among the most expensive across all music festivals. If you are the type who likes VIP at festivals be prepared to cough up a couple grand as VIP passes are priced at $2,200! Even more expensive are the accommodations in Chicago for Lollapalooza, especially now that you need at least four nights. In 2015 Chicago was the tenth most expensive city in the United States for hotel prices. You can fully expect the prices for a big event like Lollapalooza to be even worse. It's unfortunate, but if you are planning to attend Lollapalooza it's not going to be cheap. As with most travel items, the earlier you book the cheaper it will be. Hotels and houses will fill up very quickly, especially once Lollapalooza announces their lineup. The point is, don’t wait too long to book your accommodations for Lollapalooza if you are trying to snag a deal.

Con #2 of Lollapalooza – The Crowds

Lollapalooza is a monster of a music festival, attracting nearly 100,000 attendees per day. All of these people are congregated in Grant Park in downtown for Chicago, and the surrounding area. This is a lot of people in a fairly limited space. Expect lines, and lots of them – there will be a line for getting into Lollapalooza, a line to get a beer, a line to go to the bathroom, etc. If you want to get a good spot for a particular show you need to get there at least a performer in advance so you can move up and secure a good spot. Even in your good spot you will be sandwiched in there with tens of thousands of other people. I’m not trying to be a downer – part of the fun of music festivals is experiencing everything with the crowd. That said, Lollapalooza is one of the most crowded festivals there is, so if you are really bothered by big crowds it may not be for you.

Con #3 of Lollapalooza – No Age Restriction

Lollapalooza is a festival with no age restrictions at all. If you are younger this is great, but if you are an adult it can be quite annoying that so many teenagers go to Lollapalooza. Just go in knowing you will see some teenagers who have no idea how much alcohol they can consume and are ignorant to common human decency.

Con #4 of Lollapalooza – The Weather

Lollapalooza takes place every August, right in the middle of what can be a brutal Chicago summer. Expect the weather to be hot, and potentially very humid. This gets doubly worse when you are there with 100,000 other people at Lollapalooza. Additionally, Chicago is known for unpredictable weather – it could be 80 and humid, 100 and dry, or just down pouring rain. This means you need to pack for multiple scenarios, or risk being ill prepared. In years past they have even had to evacuate Lollapalooza for safety concerns due to lightning. Just know you aren’t guaranteed beautiful weather at Lollapalooza; this isn't Southern California with beautiful weather year round.

Lollapalooza Pros

That’s enough about the negative side of Lollapalooza. Let’s turn the page now and look at all the great things about the festival.

Lollapalooza Lineup

Pro #1 of Lollapalooza – Music Lineup

The nice part with Lollapalooza being so big is that they have the financial backing to afford anyone they want to book, making their lineups really strong each year. The lineups are also so eclectic that they will surely have something for every music taste. Obviously how good a lineup is considered is a subjective thing, but in general everyone seems to really like what the producers of Lollapalooza do with their lineup each year. This is a festival that sells out before the lineup is released every year after all - this wouldn't happen if people didn't know the lineup was going to be good. Lollapalooza also resists the urge to go too heavy on the EDM to attract a younger crowd, which is something I can fully appreciate.

Another perk, at least in my opinion, is that Lollapalooza is now a four-day festival. This means even more music! For Lollapalooza 2017 the festival features over 170 artists, which is the among the most of any festival. If you go to Lollapalooza you are sure to see some of your favorites and discover some great new stuff.

Pro #2 of Lollapalooza – The Food

Chicago is certainly known for its food, and Lollapalooza is no exception. Every year Lollapalooza brings in some of the best restaurants and food trucks from the Chicago area in what they deem Chow Town. Who exactly is there varies every year, but there is guaranteed to be great food each year. If you aren’t from Chicago, or have never visited, this is a great opportunity to try some Chicago classics such as giant hot dogs or deep dish pizza. It’s not all expensive either as Lollapalooza usually has a few places with some cheap options like $3 slices of pizza. You can see all the restaurants that will be at Lollapalooza on their official website.

Lolla Grant Park

Pro #3 of Lollapalooza – The Location

Lollapalooza has one of the best locations of any festival in the country. The only festivals that come to mind with such a central location in a major city are Austin City Limits, Outside Lands and Bumbershoot. Lollapalooza takes place in Grant Park, which is about as central of a location as possible in Chicago. This is a beautiful park with picturesque views and tons of restaurants and bars nearby. If you haven’t been to Chicago before it’s also really convenient as it is near all the touristy spots in Chicago like Millennium Park, Shedd Aquarium, and others. This gives you a chance to see some of Chicago and attend Lollapalooza. There are hundreds of hotels in the immediate area around Lollapalooza, so if you have the money you should have no problem finding a good hotel within walking distance.

Pro #4 of Lollapalooza – Chicago Public Transportation

Chicago has arguably the best public transportation system in the United States. There are trains, subways, and buses that cover every region of the city. Regardless of where you stay in Chicago, you will be able to get to Lollapalooza easily. Because Lolla takes place in the heart of Chicago there are multiple lines from all directions that head there. Obviously the closer you stay the easier it is to get to Lolla, but people stay as far away as O’Hare airport for Lollapalooza and get there just fine. If you can afford to stay in Downtown close to Lolla then I fully recommend you do so - there's no better way to get to Lolla than biking or walking. However, don't fret if you have to stay far away: you will be able to find a way to get to Lollapalooza with the cities public transportation. This is such a common topic for Lollapalooza that I have written a full article on how you can get to Lollapalooza from all over Chicago. You can read our full guide for getting to Lollapalooza here.

Pro #5 of Lollapalooza – Well Oiled Machine

Lollapalooza is one of the best-run festivals in the country. There are signs with proper directions everywhere, security and entering the festival is smooth, and the festival grounds are well organized. This may seem trivial, but I assure you many music festivals are not well organized and it makes the whole experience less enjoyable. Nothing is more frustrating than a festival being poorly run after you dropped $300+ on the tickets. You will not experience this at Lollapalooza as they do a great job putting on this party every August. Even when Lollapalooza had to evacuate for weather issues recently it was executed very smoothly. Lollapalooza is a well-oiled machine that you can trust to treat you well and be properly organized.


There you have it – all the pros and cons of Lollapalooza. Hopefully this helps you determine if Lollapalooza is the festival for you. I personally feel Lollapalooza is absolutely worth it - it's one of the true major music festivals in the country, and one that should be on every music fans bucket list. However, the final decision is up to you! Hopefully this article has helped you decide if Lolla is for you.

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