Staff Pick's: Chicago, IL
Music Roadtrip
Certified: 🌟 Certified
Description: Chicago is a city wired for music. Blues, jazz, rock, house, soul—every genre has left fingerprints on these streets. This route follows that lineage across neighborhoods, historic studios, record shops, and late-night rooms where the city’s sound keeps evolving. Kick things off at Choose Chicago, the city’s official tourism hub, where you can grab maps, venue tips, and neighborhood guides to help you navigate Chicago’s sprawling creative landscape. From there, head straight into history at Chess Records / Willie Dixon’s Blues Heaven Foundation, the legendary studio where Muddy Waters, Howlin’ Wolf, Etta James, and Chuck Berry carved the blueprint of modern music. Continue south to Thalia Hall, a 19th-century opera house turned Pilsen nightlife anchor, where great food and even better shows unfold beneath its ornate balcony. Then dig for treasures at Dusty Groove, one of the nation’s best vinyl shops, with deep crates of soul, jazz, funk, and global grooves. A short ride away, Reckless Records keeps the hunt alive with indie gems, new releases, and Chicago-scene essentials. As night settles in, head to Metro Chicago, a storied live-music club in Wrigleyville that has hosted everyone from R.E.M. and Nirvana to today’s rising stars. Cap the evening at The Green Mill, an Uptown icon where jazz swells beneath vintage chandeliers and the ghosts of Prohibition-era legends still whisper in the walls.