When people think of Chicago, iconic images spring to mind—towering skyscrapers like the Willis Tower, the shimmering expanse of Lake Michigan, deep-dish pizza, and the famous Cloud Gate sculpture (affectionately known as “The Bean”).
Chicago is a city of neighborhoods—77 official community areas, each with a distinct personality. While downtown (known locally as “The Loop”) is packed with must-sees, the real magic often lives in the surrounding districts.
Start with the Neighborhoods, Not the Skyline
Yes, Chicago’s deep-dish pizza is legendary—and yes, you should try it. But once you’ve sampled a slice at Lou Malnati’s or Pequod’s, dig deeper into the city’s diverse culinary landscape.
Eat Like a Local (Hint: Not Just Deep-Dish)
Navy Pier is great for families and first-timers, but if you’re looking to blend in with locals, hit the Lakefront Trail instead. This 18-mile path hugs the shoreline of Lake Michigan and offers breathtaking views of the city skyline, beaches, and parks.
Explore the Lakefront (But Not Just Navy Pier)
As night falls, the Windy City lights up. Chicago has a long and storied jazz history, and you can still catch world-class live music at venues like The Green Mill in Uptown—once a hangout of Al Capone.
Chicago After Dark: Jazz, Cocktails, and Speakeasies