Volunteer at Lollapalooza to get in free on the day you volunteer. Shifts are four hours long so you'll still have plenty of time to catch performances. Volunteers may assist the box office, help people with disabilities or help keep the park clean.
Win a contest. Many radio stations offer free tickets to Lollapalooza for contest winners. You'll need to have quick dialing fingers and some luck to win, but your reward will be free tickets.
Become a vendor at the event or work for one. If you produce an eco-friendly product, you can submit an application to Lollapalooza. The event also includes some non-profit groups' booths. By working at the event, you'll get to attend for free, although your attention will be diverted during those working hours.
Submit an application for your band to play at Lollapalooza. It's great exposure and you'll get to enjoy other acts and events as well. Of course, you'll need to put in the time and practice to be good enough to be accepted.
Cover the event for a newspaper or music outlet as part of the media. You'll need to have your credentials in order, but your employer may send you to cover Lollapalooza on their tab.
Ask for tickets as a gift. If you want to attend Lollapalooza, put tickets on your birthday or Christmas list. You may be surprised by tickets from someone that you love.