About this pick
Vape! The Grease Parody is one of our hand-picked Events finds for Chicago. Apollo Theater · 2026-11-05.
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.