Rae

Guide: Chicago
123 Spots

Windy City Wonders

Chicago is a vibrant city that blends iconic sights with local charm. As a resident of over eight years, I complied this guide that offers things to do, can’t miss landmarks, buzzing bars, and a curated list of coffee shops and restaurants across the city's diverse neighborhoods. Whether you're here for a weekend or a while, dive into Chicago’s unbeatable food scene, thriving arts, and unforgettable energy.

Lakefront Trail
Sightseeing
Sightseeing
Lakefront Trail
Scenic lakefront trail in Chicago
Wrigley Field
Sightseeing
Sightseeing
Wrigley Field
Iconic home of the Cubs
Cloud Gate
Sightseeing
Sightseeing
Cloud Gate
Reflective sculpture in Chicago Park
Cindy's Rooftop
Restaurant
Restaurant
Cindy's Rooftop
Rooftop dining with stunning views
The Second City
Culture
Culture
The Second City
Famous comedy club
Field Museum
Museum
Museum
Field Museum
Exploring natural world and history