Win a Trip to Chicago for Lollapalooza 2026: Enter the Summer Sendoff Sweepstakes

There is a particular summertime carnivalesque energy that follows Lollapalooza—three days where Grant Park in downtown Chicago feels less like a public space and more like a portable city of stages, confetti and blockbuster lineups. “Lollapalooza is three days of chaos, confetti and some of the biggest names in music taking over Grant Park in the heart of Chicago—and honestly, there’s nothing like it,” reads the sweepstakes copy, and it is hard to argue with that.

For anyone still juggling festival spreadsheets and airfare alerts, a sweepstakes called the Summer Sendoff to Lollapalooza is offering one tidy prize package that collapses a lot of logistical headaches. The Grand Prize bundles two Lollapalooza tickets, round-trip airfare for two to Chicago, and a four-night hotel stay—everything needed to get you and a guest into Grant Park from July 30 through August 2 without the usual guerrilla travel planning.

How the entry works

Entries open Saturday, June 20 and close at 11:59 p.m. on Sunday, July 12, 2026. The more you like, subscribe and share, the more chances you can rack up; one winner will be randomly chosen from all eligible entries on Monday, July 13, 2026. “One (1) winner will be randomly selected from all eligible entries received on Monday, July 13, 2026,” the official rules state. This is a multi-market contest limited to residents of the contiguous United States who are at least 18 years old, and the winner’s guest must also be 18 or older. Prize is provided by Republic Records.

Speaking to the obvious: this is not a VIP backstage pass or a meet-and-greet. It is a practical package aimed at getting two people into the festival and into the city for the weekend. For many readers, that is precisely the kind of thing that moves a festival plan from aspirational to real.

Elsewhere in our coverage, we round up some cultural detritus and context—because while Lollapalooza is the most immediate invitation, the cultural landscape around festivals and music nostalgia keeps shifting.

“Lollapalooza is three days of chaos, confetti and some of the biggest names in music taking over Grant Park in the heart of Chicago—and honestly, there’s nothing like it.” “One (1) winner will be randomly selected from all eligible entries received on Monday, July 13, 2026.”

Curious readers who want visual reading lists can also check the adjacent features. There’s a gallery that reckons with the way familiar rock acts age into the category of “dad rock,” and another that keeps a ledger of retail chains closing locations this year.

Gallery Credit: Rob Carroll