All roads lead to Lollapalooza. But forget about driving and high parking fees. The CTA is the best bet to get you close enough.
With Jackson and Balbo both closed between Michigan and Lake Shore Drive for the weekend, there will be many bus routes. The CTA
has not released final details , but they will here by Thursday night. Most buses will be rerouted to adjacent streets.
But actually, CTA rail is the best way to go. They are a bit more reliable and frequent, and again, will get you close enough. The two entrances are between Jackson and Balbo, and on Monroe at Columbus. Trains running on the Loop elevated track will get you closest: Brown, Orange, Green or Pink. Exit at Adams/Wabash or Madison/Wabash.
For users of the both the Red and Blue lines, exit at Monroe or Jackson. CTA will operate longer trains more frequently.
Finally, pay attention to your surroundings. Notice who is there, who might be watching you. Don't be a victim.
And have some fun.