Lollapalooza Survival Guide 2018 – 29 Tips to Save Money & Time

Posted on: November 15, 2018, by :

Lollapalooza Survival Guide 2018 – 29 Tips to Save Money & Time

I’m not the hippest kid on the block. I watch the pop culture scene with maybe one-quarter of one eye, when I feel like it. I stopped seeking out new music years ago. I’m not confident I could name any artists on the pop charts right now.

My wife is much more in tune. So, it didn’t come as a total shock when she approached me in early 2017 with a proposal: Let’s go to Lollapalooza this year. Actually, it was an ultimatum. She’d already purchased our tickets.

She’s culturally attuned, for sure, but neither of us are really “festival people.” What saved the deal for me was Lollapalooza’s location – right in the middle of Chicago, near the Lake Michigan waterfront in Grant Park. It’s a stunning, super-convenient spot, within easy reach of the city’s top restaurants, museums, performing venues, and parks.

Anyway, my wife was between jobs, and this would be our last chance for the foreseeable future to experience any music festival firsthand. Plus, I knew it’d be a great opportunity to put together a guide for frugal Lollapalooza visitors. What follows is an unbiased, unvarnished look at doing Lollapalooza safely and (relatively) affordably.

Curious about Lollapalooza’s backstory? Here’s a quick overview of Lollapalooza – or Lolla, as it’s known colloquially.

Lollapalooza got its start as a one-off, multicity tour in 1991. Jane’s Addiction front man Perry Farrell planned Lolla as an extended farewell for his band, but its initial popularity convinced Farrell and the other organizers to plan a revival in 1992. A second successful year begat a third, fourth, and fifth. Even as its popularity increased, Lolla’s core ideal remained the same: showcasing the breadth and diversity of the then-vibrant alternative rock scene.

Farrell remained involved until 1996, when he stepped back to focus on other projects. The 1996 and 1997 editions of Lollapalooza were poorly received for a variety of reasons, and the 1998 edition was cancelled when organizers couldn’t find a suitable headline act in time.

The concept remained moribund for five years. In 2003, Jane’s Addiction announced a reunion tour, and Farrell decided it was time to give Lolla another shot. Though the 2003 and 2004 editions sold poorly, the rebirth wasn’t a total failure. So, in 2005, Farrell partnered with a seasoned event promotion company to professionalize Lollapalooza.

The team reimagined Lolla as a destination festival and chose Chicago’s Grant Park as the permanent venue. Since 2005, Lolla has been synonymous with Grant Park – though Chicago isn’t the only host city anymore. In 2011, the festival expanded to Santiago, Chile, and now hits nearly a dozen cities around the world throughout the year. Chicago remains Lolla’s home base and largest single event.

Farrell and company expanded Lolla to the current four-day format in 2015. Visitor counts have swelled in recent years. In 2017, organizers and city authorities expected as many as 400,000 visitors to come through over the course of the festival. According to Lolla’s website, the 2017 edition featured 170 performing acts on eight stages and 35 food vendors, all affiliated with popular Chicago restaurants.

Lollapalooza 2018 starts on Thursday, August 2, 2018, and runs through Sunday, August 5, 2018. As always, it’s happening in Chicago’s Grant Park.

I’m not going to reprint everything on Lollapalooza’s excellent festival information page. If you’re serious about checking Lolla out in 2018 and beyond, please spend some time there.

Since they’ll do more than anything else to determine whether Lolla is financially realistic for you, I do want to outline the festival’s three admission tiers.

General Admission
Most Lolla-goers buy general admission tickets. They’re pricey enough: $335 for a four-day pass or $120 for a day pass, as of 2017. Lolla hasn’t yet announced 2018 general admission prices. (Prices have steadily risen over time, however.)

2018 general admission passes officially go on sale in conjunction with the festival’s lineup announcement in late March. General admission passes typically sell out within hours. Resale values then rise for a while, level off, and eventually fall as the festival’s start date nears.

If you miss the initial sales window, as many Lolla-goers do, you can probably score a four-day pass for less than $400 on the secondary market. 2018 tickets are already available on resale sites like TicketCity. I found four-day passes for $357 and up on TicketCity, roughly in line with first-sale pricing. If you buy before passes officially go on sale, you won’t actually receive your pass until after the launch date.

General admission entitles you to:

VIP Admission
2018 VIP admission costs $2,200 for a four-day pass, or $650 for a single-day pass. Yes, you read that right. As a VIP guest, you’re entitled to:

Platinum VIP Admission
2018 Platinum VIP admission costs $4,200 for a four-day pass, or $2,800 for a single-day pass. Yes, you read that right. Your investment entitles you to everything those lowly VIP guests get, plus:

Platinum and VIP guests have free reign of the general admission areas as well, but it’s hard to imagine why they’d want to step outside the cozy confines of their lounges.

Pro Tip: Protect your Lollapalooza ticket purchase with a form of travel insurance by opting into Front Gate Tickets’ Secure Ticket™ feature. For a 9.2% surcharge on your ticket’s face value, Secure Ticket™ guarantees you a full refund if you have to cancel your trip for certain covered reasons. Check out the Secure Ticket™ terms and conditions for more details.

Lollapalooza takes over pretty much all of Grant Park. The layout seems to change a bit each year, so you’ll want to check the official website for the latest map.

This Chicago Tribune schematic from 2017 is a good first pass – it shows the stages, food vendors, bars, hydration stations, and cooling facilities. Monroe, Jackson, Columbus, and Balbo are all closed for the duration of the festival. Michigan is closed between Randolph and Roosevelt after the festival, when tens of thousands of revelers stream out into the city.

Columbus is the main pedestrian thoroughfare through Lolla. There’s a back way that cuts through along the Buckingham Fountain axis (more on that below) and some other useful paths around the park.

If you don’t get stuck in a crowd, it takes about 12 minutes to walk briskly from the north entrance (Monroe and Columbus) to the Grant Park stage – the longest distance you’ll have to cover in one go at the festival. Throngs lengthen transit times. In the evening, we’d budget 15 minutes to get from the west (main) entrance on Congress Parkway to either the Bud Light or Grant Park stages.

For the most part, Lollapalooza is not a kid-friendly event. The exception is Kidapalooza, a semi-independent event held in a fenced-off section of Grant Park. Ironically, or perhaps not, Kidapalooza is the best deal at Lollapalooza: Kids under 10 get in free with general-admission parents. If you’d rather not leave your small children with the babysitter (or grandma), this is your jam.

Kidapalooza has family-friendly music from 11am to 7pm all four days, plus a slew of fun, age-appropriate activities for tykes.

The Tag-a-Kid booth, where you can register your child and get a wristband for him or her, is reason enough to at least stop by Kidapalooza. “In the instance that a child gets lost, we have a way to unite them with their parent,” reads the Tag-a-Kid section of Lolla’s Kidapalooza page.

Planning a trip to Lollapalooza this year or next? Follow these tips to reduce your expenses and save yourself logistical headaches before you even set foot in Grant Park.

If I ever do Lollapalooza again, I’m following this advice. By Sunday, we were pretty tuckered out from an extended weekend of walking, biking, and mainlining loud music.

At $120 apiece, one-day general admission passes aren’t cheap, but they’re still easier on your budget than four-day passes. Come for Saturday or Sunday (or both) and you might not have to take a day off work.

You can still make a vacation out of Lolla without a four-day general admission pass. Hit the festival one or two days, then spend the rest of your time in Chicago exploring the city. You won’t run out of things to do, I promise.

This is an admittedly risky strategy. But, if your travel plans are flexible or you already know you’ll be in Chicago during Lolla, it’s realistic. Passholders whose plans have changed are increasingly desperate to sell as the festival approaches. We saw passes advertised at 50% off face value 10 days before the event – enough to make us question our decision to buy as soon as possible.

There are some restrictions on how, where, and when you can resell your Lolla passes. Check with the festival’s organizers for the lowdown.

Our four-day Lolla passes cost $335 apiece. That’s already prohibitive for millions of frugal music fans. VIP passes cost six times more. And let’s not even talk about Platinum passes.

We had a great time hanging out with the unwashed masses. We saw all the acts we wanted to see, with good to great sight lines. The worst mishaps we suffered involved long entry lines and internal crowds, but those didn’t really move the needle on our overall experience. We escaped without completely destroying our budget for the year.

Sure, you get a lot for your VIP or Platinum Pass, but is it really worth it? Probably not.

Before firming up your travel plans, consider combining forces with other Lolla-goers and carpooling to Chicago. I’m not saying you need to put up a Craigslist ad and accept a ride offer from a total stranger. That’s a recipe for regret. Reach out to those you trust, or at least know by association: colleagues, classmates, friends, friends of friends.

This isn’t exactly earth-shattering advice, but it bears repeating. Chicago is a major city with two busy airports. Oft-forgotten Midway, a compact little facility tucked away on the city’s southwest side, is almost entirely given over to Southwest Airlines, the country’s best-known discount airline. If you’re flying in from a major U.S. city, you can probably snag a direct Southwest flight to Midway, from which it’s an easy jaunt to Grant Park on the El.

We seriously considered flying Southwest to Midway from Minneapolis. It ended up being slightly cheaper to drive, and the prospect of catching up with an old friend along the way sealed the deal. Had our journey been any longer, though, we definitely would have flown.

Pro Tip: Flying Southwest to Lolla? Before you go, apply for one of Southwest’s two consumer credit cards: Chase Southwest Airlines Rapid Rewards Plus Credit Card or Chase Southwest Airlines Rapid Rewards Premier Credit Card. Use yours enough and your next Lolla flight might just be free.

You can get a truly great deal on Lollapalooza wristbands once the festival has already started. The catch: You have to get them from the scalpers congregating around Grant Park.

This approach has too many risks to warrant serious consideration. The biggest is simply that you won’t find out your wristband doesn’t work until you try to enter the festival grounds. It’s not like you can ask your scalper for a refund.

According to this handy Lollapalooza tip sheet from Time Money, nightly hotel room rates rose some 55% across Chicago in advance of Lollapalooza 2017. The most conveniently located hotels, within walking distance of Grant Park, charged a whopping 77% higher than their baseline rates during the festival.

You can find a decently priced hotel for Lollapalooza – it just won’t be in downtown Chicago. Look to nearby suburbs with good transit connections to Chicago and plenty of hotel options: Evanston, Skokie, Park Ridge, and Des Plaines all work. (Park Ridge and Des Plaines are close to O’Hare International Airport, so they’re super convenient for Lolla-goers flying in from elsewhere.)

Chicago is the third-biggest city in the United States. The Chicagoland metro area has nine million residents, give or take. Even if you’ve never been to Chicago, there’s a not-insignificant chance that you know a local well enough to crash on their couch for a couple nights.

Early in the planning process, my wife and I made a list of people we knew in Chicago. We came up with about a dozen names, mostly former high school and college classmates with whom we’d been out of regular contact. We were tempted to reach out to a few to try to strike a deal – perhaps a reasonable, under-the-table cash payment or generous post-stay gift.

Ultimately, we decided that an Airbnb rental would be more private and less intrusive. We’d be coming back to our home base after midnight each night, and we didn’t want to put out people we didn’t really know that well. Still, it doesn’t hurt to reach out to locals before you make other plans. Worst case scenario, they ignore your email or text.

If you don’t have friends in town, or aren’t sure about putting them out for an extended weekend, do what we did: Rent modest digs on Airbnb, HomeAway, or another reputable short-term rental platform.

We got a private room in a walk-up on Chicago’s North Side. The neighborhood was great – quiet, yet close to tons of restaurants and bars. The 606, a disused elevated rail line that’s now a popular multiuse path, was just steps from our door. We had a secure indoor place to store our bikes. Though we didn’t have the place to ourselves, our host was super accommodating and gave us our space. And we spent well under $100 per night – half the cost of a hotel room anywhere in the city.

All told, we couldn’t have been happier with the place and its value. If you’re willing to go farther out, to Chicago’s first- and second-ring suburbs, you’ll no doubt find even better deals.

Pro Tip: It won’t help reduce your Lolla costs directly, but that doesn’t mean you shouldn’t consider a tourist discount pass or booklet from CityPASS or Smart Destinations. Both offer bulk or a la carte admission and service discounts in and around Chicago. If you plan to work some non-Lolla activities around your festival experience, they’re worth looking into.

Once you arrive in Chicago, follow these tips to stretch your Lolla dollars (and sanity) further.

The El, Chicago’s rail rapid transit system, is more than a century old. It’s notoriously slow and unreliable in the best of times.

Lollapalooza is not the best of times. I can’t go so far as to advise against using the El under any circumstances during your Lolla trip, but – at a minimum – you should expect it to be an adventure. We stayed less than half a mile from an El stop, so it was theoretically convenient to take the train. After a rough evening ride, complete with a multi-block line into the station and a heroic effort to pack far enough into the car to allow the doors to shut, we resolved to make alternate arrangements on the following days.

Good thing we brought our bikes to Chicago. For the next three days, we made like true bike commuters and rode downtown from our place each afternoon, a distance of about six miles one way. It was way easier, and a whole lot healthier, than riding the El.

If you don’t have the luxury of bringing your own bike to Chicago, and you don’t want to pay insane surge pricing to catch an Uber or Lyft home from Lolla each night, look into Divvy, Chicago’s excellent bike sharing network. The stations around Grant Park will likely be over capacity, but you can probably find a bike if you’re willing to walk a few blocks in any direction. If you’re not staying close to a Divvy station, use the app to find a station partway home and use that as a transfer point to catch the bus or grab a more reasonably priced rideshare.

Even if you’re not super jazzed about the first day’s schedule, get there as early as possible and hit the will-call stand to pick up your wristband. We arrived at 1:30pm or so on Thursday and still had to wait almost an hour to grab our bands. You don’t have to enter the festival right away – your pick-up rendezvous might turn into an opportunity to check out the nearby Field Museum or Shedd Aquarium on an uncrowded weekday afternoon.

Every vendor I encountered at Lolla accepted credit cards, and Internet connectivity was never a major issue. (A few transactions were slowed by heavy network use.) I don’t think I used cash for a single transaction inside the festival grounds. It was nice not to have to worry about carrying around much paper money in a big, unruly crowd.

For even faster payment, consider using Lolla Cashless, a secure mobile contactless payment system that uses your wristband’s RFID transmitter. It’s fairly easy to set up when you activate your wristband.

This is easier said than done when you’re planning to spend an entire afternoon and evening away from home, exposed to the elements, but try not to bring a bag into Lollapalooza. Everyone entering Lolla’s secure area is subject to search. For bag-toting visitors, that means a thorough pat-down and a long glance inside the pouch – a 20-to-30 second ordeal. Multiply that by thousands of visitors, divide by perhaps eight to ten bag-checkers, and you get some idea of the time involved.

We were fortunate enough not to contend with serious security lines until Saturday, when it was warm, sunny, and very busy. I stood in line for about 45 minutes, watching nervously as sun- and booze-addled revelers jostled one another for position. (One fight nearly broke out in front of me, but fortunately cooler heads prevailed before anyone got hurt.)

If you can’t carry everything in your pockets or purse, share a bag with your partner. (If you’re part of a larger group, try to fit everything the group needs into a single bag.)

Given the sheer volume of visitors, I was surprised by security’s diligence. While they didn’t open every single hidden compartment in my shoulder bag, they definitely would have found (or at least felt) any bulky contraband items in there. Don’t tempt fate by bringing anything you wouldn’t want security to find.

If you get cold feet before you enter, you can use the “amnesty bins” just outside the security gate. They’re big, unsupervised trash bins for dumping contraband, no questions asked. And, to avoid unwittingly bringing anything illicit into the festival, be sure to check Lolla’s information page for a full list of prohibited items. It’s pretty long and always changing.

Getting stuck in the security line for 45 minutes was no fun at all. I can’t guarantee that you’ll completely avoid lines by timing your arrival right, but it’s indisputable that entry volumes peak from mid to late afternoon. To beat the lines, arrive earlier in the afternoon, before 2pm, or later in the evening – after 7pm. And try the north entrance if the main entrance is packed. We had much better luck up there.

Pro Tip: Daily lineups do affect entry volumes. Bigger acts usually play later in the evening, during the 7pm and 8:45pm sets. But the pattern breaks down when local artists or acts with rabid followings perform. For instance, the biggest crowds of our year coincided with Chicago native Chance the Rapper’s evening set. Check the schedule before you leave for the park and time your entry accordingly.

The weather mostly cooperated for our Lolla adventure. The hottest day, Saturday, was sunny and maybe 82 degrees – pretty bearable for Chicago in August. The other days saw highs in the 60s and 70s. It did rain a couple times though, and a severe thunderstorm on Thursday night cut short the festival’s final act.

I’d take cool, wet weather over hot, muggy conditions any day, but I might be singing a different tune had we forgotten rain gear. We actually spent $10 to purchase ponchos specially for the festival – probably the single best purchase we made all week. (Umbrellas aren’t allowed inside the festival.) I strongly recommend doing the same, even if the weather looks clear for the duration of the event – summer thunderstorms can strike with little warning.

And bring a towel to sit on. Even if the ground is dry, it’ll keep your clothes clean – Grant Park’s grass gets pretty beat up by the end of the weekend.

Lolla security doesn’t allow any liquids in unsealed containers. If it’s still factory-sealed, fine – otherwise, whatever’s inside gets dumped in the trash.

Bottled water is a rip-off at Lolla, and recycling bins fill up quickly. (I’m skeptical that the bottles lying next to the bins actually make it into the stream.) Avoid paying festival prices for the privilege of hydrating and bring a large, empty water bottle into Grant Park with you. You can fill up at one of the many hydration stations around the park – though the lines can be a bear on hot, busy days.

girl carry empty water girl carry empty water 18. Fill Up Before You Arrive

Lolla partners with nearly three-dozen food vendors, all based in Chicago and some quite well-known to locals, to keep its patrons satiated. The selection is surprisingly eclectic: We had Chicago-style pizza and sausages (obviously), but also pork buns, mac and cheese on a stick (weird but good), multiple kinds of noodles, and some other stuff I ate too fast to remember.

We paid dearly for the privilege though. It was hard to fill up at Lolla for less than $10 per person, which really adds up over the course of four days (eight full meals, plus the occasional between-meals snack). On the second day, we crunched the numbers and decided it would be more cost-effective to eat a big lunch before arriving at Grant Park, tide ourselves over with snacks brought from outside, and eat a smaller dinner before the closing act each night.

It worked pretty well. We got to try three affordable, unpretentious eateries in the neighborhood around our Airbnb, and we likely saved $40 to $50 between the two of us.

Lolla is a great opportunity to sample Chicago’s bar and brewery scene too. Every day, before we arrived at Grant Park, my wife and I tried a different brewery somewhere in the city. It was a great way to indulge our taste for craft beer and avoid buying too many overpriced drinks inside the festival. The standard price for a 16-ounce, 6-to-7% ABV brew at neighborhood Chicago breweries and bars is $6 or $7 – not cheap, but a far cry from $9 to $10 for a watery Bud Light.

If you plan to purchase adult beverages inside Lollapalooza, you’ll have plenty of options. Outdoor bars selling the aforementioned $9 to $10 Bud Lights, plus a few other macrobrew options at similar price points, are ubiquitous. There’s also a “craft beer” bar selling $10 pints. (All the brands are owned by Anheuser-Busch, cheapening the experience a bit.) And there’s a wine bar – more on that below.

One place you definitely don’t want to buy drinks is the “cocktail bar,” which in 2017 was on the western edge of Grant Park, overlooking Lake Shore Drive. The cocktail bar looks tempting because it’s fenced-in, relatively uncrowded, and 21+ (you have to show ID to get in). In fact, it’s an ideal place for older attendees to congregate and mingle away from the throngs of high schoolers and college-age kids.

It’s fine to hang out there – just don’t buy a drink there. The cocktails are watery (mostly ice) and weak, with maybe one full measure of liquor, and they cost $14 apiece. My wife and I visited once, learned our lesson, and never returned. Don’t make the same mistake.

The first thing I remember seeing upon entering Lolla’s main gate on Thursday afternoon was a young woman drinking red wine straight out of a plastic carafe. Pretty aggressive, I said to myself. Then I looked around and saw a sea of carafe-clutching Lolla-goers before me. Hmm.

It’s not that Lolla attracts wine connoisseurs. It’s that these unassuming carafes of Cupcake wine were far and away Lolla’s best booze deal. Yes, they were $27 each, which sounds like a rip-off next to the $7 or $8 you’d pay for the same amount at your local liquor store. But the equivalent beer share would set you back $40 or $50, depending on the size of the pour. And the carafes come with cups, so you can share with your partner without swigging right out of the container.

You can buy these relatively affordable carafes at regular outdoor bars and the Cupcake wine bar, a gigantic tent near the festival’s geographical center. If you want to imbibe at Lolla without spending a fortune, learn to love them.

As soon as you get to Lolla, consult a map of the grounds. One of the first things you’ll notice is that there are lots of portable toilets – a good problem to have amid tens of thousands of partiers, many no doubt overindulging.

But not all portable toilet pods are created equal. The most obvious clusters flank the festival grounds’ central boulevard. One, right near a bank of food stalls and bars, is particularly prominent – and reliably chaotic. On the second day, which wasn’t as busy as the third, my wife and I waited at least 20 minutes for a free stall there.

Other pods are less obvious. Those are the ones you want to find. By the third day, we’d located a hidden gem: a smallish cluster of portable toilets beyond the Bud Light stage, in the extreme northeastern corner of the park. We never had to wait for a free stall here, even when the stage was active. The obvious downside was the distance from other stages, but walking beats standing in line.

Columbus Drive bisects Grant Park the long way, from north to south. During Lolla, it’s closed to vehicle traffic and basically serves as the festival’s main street. You’ll undoubtedly use it to travel between stages, food vendors, bathrooms, and quieter spots throughout the festival.

Don’t rely on it too much though. By midafternoon, especially on Saturday, it’s completely packed. Much of its eastern edge is occupied by food and beverage vendors, whose queues force pedestrians into narrower, even more congested lanes. More often than not, our walks along Columbus Drive were little more than lazy shuffles, and our transit times rose correspondingly. The mess cost us the start of two sets, though fortunately we were able to see most of both.

The best alternative to Columbus Drive is further east – a wide pedestrian thoroughfare that connects the northern end of the park (at the Bud Light stage) to the southern half, passing Buckingham Fountain. It doesn’t go all the way through, but it’s relatively straightforward (and usually not too congested) to get from the southern terminus to the two southeastern stages.

These tips might not directly impact your bottom line, but they’ll still save you (and others) a world of trouble.

Don’t forget sun protection, even if you don’t burn easily. With a couple noteworthy exceptions, Lolla’s venues have limited cover. During afternoon sets, the sun can be intense.

It doesn’t hurt to pack bug spray either. We didn’t see (or feel) many mosquitoes at Lolla, but Grant Park is built on former swampland within sight of Lake Michigan. It’s a bug-friendly environment.

Trust me: They make multiple hours of screaming-loud music a lot more bearable, and it’s actually easier to carry on a conversation with earplugs besides. If you’re an audiophile, splurge on musicians’ earplugs, which can cost upwards of $15 per pack. Otherwise, hit a Walgreens near Grant Park on Thursday and grab a $6 pouch of regular foam plugs. That should be enough to last through the weekend.

Don’t let your beverage out of your sight, period. The statistical likelihood that someone will slip something in your drink is quite small, but it’s not worth the risk.

Duh. Take all of your things with you, all the time, even if you’re not walking out of eyeshot. It’s painfully easy to steal stuff in a crowd, and the cops patrolling Lolla have better things to do than help you find your purse. There is a lost and found on-site, and you should absolutely check there if and when you misplace something, but don’t bet on a favorable resolution.

Thankfully, the near-fistfight referenced above is the closest I came to witnessing person-on-person violence at Lollapalooza. A heavy police presence probably did more to keep things safe than anything.

That said, any situation involving drugs, alcohol, large groups of people, and waiting is inherently combustible. Don’t overestimate the danger or preoccupy yourself with worry, but do keep an eye out for signs of trouble, such as sharp exchanges (preludes to fights), sudden flows of people from one place to another (indications of crushes or stampedes), and police activity (hints that an altercation may already be in progress).

Your own safety comes first. If you get the sense that you’re close to a situation that could escalate, move to safer ground before doing anything else. Then alert the authorities, if it’s safe and appropriate to do so. Don’t spectate – in dynamic crowds, bystanders become part of the action in the blink of an eye.

This is a tricky one. You don’t want to step on others’ toes or get in the way of anyone’s good time. But I’d argue that you have a moral obligation to speak up when you see someone in distress – or even someone who might be in distress.

An example: My wife and I were walking up a grassy hillside after a set when we came upon a guy lying face down on the ground – like, nose in the dirt. He was completely motionless, clearly unconscious. We looked around, then at each other, then back at him. At first, it wasn’t totally clear that he was breathing. After a few seconds, we determined that he was, but slowly and shallowly enough that it seemed like a good idea to let someone else know. We asked the nearest group if they knew the guy. They did, fortunately, though they admitted they hadn’t paid much attention to him for the duration of the set. We explained what we’d seen and gently suggested that they try to wake him up, then left.

My last glance back revealed a concerted effort to wake the guy up and some stirring on his part, so I’m pretty sure things turned out okay. He probably would have been fine had we not said anything, but I’m glad we did.

Many of these tips and tricks apply to music and entertainment festivals in general, not just Lollapalooza. But Lollapalooza is notable, if not quite unusual, for its location smack in the middle of the United States’ third-largest city.

Lolla’s location was actually a big selling point for my wife and me. As I said up top, we’re not really “festival people.” Out-of-the-way events like Bonnaroo (in rural Tennessee) and Coachella (in California’s Mojave Desert) have never been on our radar. We saw Lolla as an opportunity to visit Chicago for the first time in a few years and do some sightseeing and exploring while there.

The result was a mixed bag.

In the loss column: our attempt to explore the big museum campus just south of Grant Park. It was inundated with tourists; we spent 45 minutes waiting in line at the Shedd Aquarium before giving up and heading back to Lolla. Our mistake was trying to get in on Saturday, the busiest day of the festival by far.

In the win column: our visits to a handful of low-key Chicago attractions. We had a couple great runs on the 606, an elevated multiuse trail near where we stayed on the North Side; patronized two awesome craft breweries that we’d long wanted to try (plus a couple other cool watering holes); and spent a leisurely hour at the American Writers Museum, a really cool collection that had just opened the previous year.

If you want your Lolla trip to include some bonus Chicago exploration time, learn from our experience and do some advance planning. Think outside the box. And save money on sightseeing with discounts from CityPASS or Smart Destinations!

Have you ever been to Lollapalooza? How did you control your spending and minimize the impact to your budget?

Categories: Entertainment, Lifestyle, Travel

Brian Martucci writes about frugal living, entrepreneurship, and innovative ideas. When he’s not interviewing small business owners or investigating time- and money-saving strategies for Money Crashers readers, he’s probably out exploring a new trail or sampling a novel cuisine. Find him on Twitter @Brian_Martucci.

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