Chicago is a city of world-class music—the blues, jazz, country, and modern rock have all left an indelible impact on the city.


From touring musicians to local heroes, live music is never too far away from The Guesthouse—in fact, some places to catch a concert are just a walk down the street!

The Aragon
(.6 miles from Guesthouse)

Rivera Theatre
(.6 miles from Guesthouse)

Metro Chicago
(1.5 miles from Guesthouse)

Old Town School of Folk Music
(1.4 miles from Guesthouse)

Simon's Tavern
(.4 miles from Guesthouse)
This 80-year-old tavern features live music—from swing country bands to eclectic cover bands—every Wednesday and Sunday night.




Lollapalooza (early August) 
The granddaddy of modern music festivals makes itself home along Lake Michigan each year.

Pitchfork Festival (mid July)
This brainchild of the venerable online music magazine of the same showcases cutting-edge artists.

Riot Fest (mid September)
A three-day music festival and carnival that brings to the stage legendary bands and up-and-comers.

Taste of Chicago (mid July)
An eclectic line-up of well-known artists usually headlines this summer festival. Lawn seating is free—but you can also pony up $15 for a closer view!

Chicago Blues Festival (mid June)
Chicago is the "Blues Capital of the World," and for three days you can be front and center before world-class artists.

Downtown Sound (Mondays, throughout the summer)
From indie rock to world music, Downtown Sound is a contemporary showcase of musicians from around the world—and it's free!