Lollapalooza, August 1-3 in Grant Park, is one of the largest music festivals in the nation and one of Chicago's top destination events, with last year's installation reportedly drawing more than 100,000 attendees per day. Outside of the crowd and the expansive festival site, the size of the artist roster alone is enough to make the three-day, genre-spanning festival daunting and difficult to navigate.

The festival headliners for Lollapalooza 2014 - Eminem and Arctic Monkeys on Friday, Outkast and Calvin Harris on Saturday, and Kings of Leon and Skrillex on Sunday - may be household names, but they make up only a small fraction of the vast assortment of music performances to be seen at Lollapalooza.

With that in mind, here are five artists you definitely shouldn't miss:


Into It. Over It.

Evan Weiss Lolla

Chicago-based indie-folk troubadour Evan Weiss, a.k.a. Into It. Over It. started out as a solo act. Over the years, IIOI has evolved into a full band with a revolving cast of musicians. Weiss' work as IIOI meanders back and forth between lo-fi/acoustic tunes and garage indie rock, with an obvious and clear affection for late '90s emo popularized by groups like Sunny Day Real Estate and Death Cab for Cutie. Catchy hooks, courtesy of a decidedly Midwestern pop-punk sensibility, color IIOI's sound as well, making for a well-rounded, enjoyable listening experience.


J. Roddy Walston & the Business

J. Roddy Walston & the Business

Blues, 1960s garage rock, and a hint of traditional roots music come together in the rock ‘n' roll frontal assault that is J. Roddy Walston & the Business. On their newest record, "Essential Tremors (LABEL)," J. Roddy et al. touch on a little bit of everything — you'll hear everything from soulful, R&B tinged vocal harmonies to guitar-driven fierceness accompanied by Walston's cutting falsetto.


Lykke Li

Lykke Li

Swedish songbird Lykke Li's brand of indie-pop is appropriately dominated by her strong voice, often sounding vast and slightly haunting as it ducks and weaves through orchestral and electronic accompaniment. Her most recent work, I Never Learn (LL, 2014), is both her shortest and her most complex — an ode to a breakup that saw Li move across the world, she captures the pain and uncertainty of such events in a way that makes it feel like she's singing your feelings.


Jon Batiste and Stay Human

Jon Batiste

When trying to describe Jon Batiste and Stay Human, the easiest thing to say is the group pushes musical boundaries whenever possible. Batiste, an accomplished multi-instrumentalist of New Orleanian origin, grew up in the rich musical tradition of the Delta. Batiste's strong background in New Orleanian jazz is obvious in his work, but elements of funk, R&B, pop, hip hop and even classical music make an appearance.


Childish Gambino

Childish Gambino

As a lyricist, Donald Glover, a.k.a. Childish Gambino, brings the same acerbic wit and intellectual humor he demonstrated as a comedy writer for shows like 30 Rock and as a member of the ensemble cast of Community. Glover has utilized his musical career to explore deeper, more difficult aspects of life — his outsider feelings as a child and the exploration of racial stereotypes colored much of his earliest work.


Lollapalooza 2014 full lineup, by day:

Friday, August 1: Eminem, Arctic Monkeys, Lorde, Zedd, Above & Beyond, Broken Bells, Interpol, Lykke Li, Phantogram, Chvrches, The Glitch Mob, Portugal the Man, Dimitri Vegas & Like Mike, AFI, J. Roddy Walston & the Business, the Kooks, Rudimental, Iggy Azalea, Bombay Bicycle Club, Warpaint, Kodaline, Sander Kleinenberg, Lucius, Blood Orange, Perry/Etty vs Joachim Garraud, Jagwar Ma, Temples, Vic Mensa, Francisca Valenzuela, Into It. Over It, Courtney Barnett, San Fermin, Roadkill Ghost Choir, Brillz, Jacob Plant, the So So Glos, Cash Cash, Bebe Rexha, Wallpaper, Dugas, Bagheera, Of Verona, Highly Suspect.


Saturday, August 2: Outkast, Calvin Harris, Foster the People, Krewella, Nas, Spoon, the Head and the Heart, Chase & Status, Cut Copy, Fitz & the Tantrums, Grouplove, Gramatik, Jenny Lewis, Manchester Orchestra, John Butler Trio, Martin Garrix, Phosphorescent, Duke Dumont, the Temper Trap, Joachim Garraud, Typhoon, Z-Trip, Kate Nash, Vance Joy, Rich Homie Quan, Parquet Courts, Smallpools, Jungle, Wildcat! Wildcat!, Papa, the Districts, heRobust, Royal Blood, Ratking, Meg Myers, Joywave, Desert Noises, Jon Batiste and Stay Human, Benjamin Booker, The Last Internationale, Johnnyswim, Charlie Hirsch, Anna Lunoe, Rocky Business.


Sunday, August 3: Kings of Leon, Skrillex, the Avett Brothers, Sebastian Ingrosso, Childish Gambino, Cage the Elephant, Young the Giant, Chance the Rapper, Flosstradamus, Chromeo, Darkside, The 1975, Rebelution, Glen Hansard, Gesaffelstein, Flume, Trombone Shorty & Orleans Avenue, Run the Jewels, The Airborne Toxic Event, London Grammar, White Denim, Delta Rae, RAC, GTA, jhene aiko, Kongos, Nonono, Gemini Club, Crizzly, Bomba Estereo, Bleachers, Bear Hands, Kausea, Bronze Radio Return, Lindsay Lowend, Betty Who, Fly Golden Eagle, Crass Mammoth, Cardiknox, Space Capone, Plastic Visions, Oyinda.


by Moira Nestmann 

Photos Courtesy of (under Creative Commons): viviandnguyen_ via flickr; Abby Gillardi via flickr; basic sounds via flickr; rufus via Flickr; Eli Watson via flickr