Check Out Smashing Pumpkins, Case Oats, Whethan And Other Local Acts At Lollapalooza 2026 is one of our hand-picked city-news finds for Chicago. Musical acts from the Chicago area performing at Lollapalooza this year include South Side rapper Ric Wilson, house music star John Summit,.
Why Chicago? Chicago is a lakefront city of bold architecture, deep-dish pride and neighborhood-by-neighborhood character along Lake Michigan. The city is known for architecture and skyscrapers, deep-dish pizza, blues and jazz and the lakefront.
Good to know: Summer and early autumn are glorious on the lakefront; winters are famously cold and windy. The 'L' train and buses cover the city; the lakefront trail is ideal for walking and biking.