100 Things to Do in Chicago Before You Die

Soaring skyscrapers, deep-dish pizza, and improv comedy may be what the city is best known for, but they are only the beginning of Chicago’s story. It could take a lifetime to experience everything this one-of-a-kind town has to offer. But what if you only have a few days to explore? You're in luck! The one hundred adventures in this candid insider’s guide promise an authentic taste of the Windy City whether you’re taking a weekend-sized bite or sticking around for the buffet of a lifetime. You’ll find seasonal and themed itineraries to make planning your explorations easier. Discover which blues club locals swear by, pay a visit to a quiet green space hidden in plain sight, or dig in to an ice cream cone piled high with five different flavors! If you’re visiting for the first time, or you’re lucky enough to call Chicago home, these one hundred iconic experiences should top your to-do list. No matter when you visit or how long you stay, as you cross off each item, you’re certain to learn something new and have fun in the process.


As a writer and Chicago tour guide, Molly Page turned a passion for living life as a tourist into her career. She’s a devoted consumer of culture and a perpetual student of Chicago’s history and architecture.