CHICAGO MUSICAL ODYSSEY

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UNLOCK THE RHYTHM OF THE WINDY CITY IN 3 DAYS!

Immerse yourself in the vibrant symphony of Chicago’s music scene as you embark on a rhythmic journey through iconic venues, historic neighborhoods, and eclectic sounds. 

Day 1: Downtown Beats

Start your day in the heart of River North with brunch at the Hard Rock Cafe Chicago, where the iconic giant guitar lights up the neighborhood. For over 30 years, Hard Rock Café has seamlessly blended funky styles with legendary food, beverages, and live music. Explore one of the world’s largest collections of music memorabilia, including pieces from icons like Billy Joel, Buddy Guy, Jimi Hendrix, and Prince!

In the afternoon, take a stroll through the Loop and make sure to stop at the Chicago Symphony Orchestra and the Symphony Store where you can find CSO merch, gifts, apparel and much more. 

For dinner, head to Andy’s Jazz Club & Restaurant for a perfect combination of live jazz music and a good meal. 


As the night falls, let loose in Chicago’s vibrant nightlife at Redhead Piano Bar, the city’s premier piano bar since 1993. With nightly live piano performances, a heated outdoor patio, and a curated humidor with over 150 cigars, The Redhead offers a vibrant atmosphere for late-night revelry, fostering congeniality, warmth, and the timeless spirit of classic Chicago nightlife.

Day 2: South Side Groove


On Day 2, embark on a journey through Bronzeville, Chicago’s historic Black Metropolis, where each street echoes with the resonance of its rich history. Discover the vibrant legacy of the 1950s, a time when Bronzeville thrived as a center for commerce, celebrated music clubs like the iconic Sunset Cafe, and housed a community of intellectuals and activists. Today, this neighborhood proudly embraces its heritage, inviting you to experience its soulful rhythms, from civil rights to the beats of jazz, blues, and gospel music. Amidst the charming Victorian-era architecture and 19th-century mansions, explore coffee shops, bistros, galleries, and more, creating a captivating experience deeply rooted in Bronzeville’s cultural tapestry.

Join the locals for the southern comfort food lunch buffet at Pearl Club. 

In the afternoon, let the rhythm guide you to the nearby South Loop. At 2120 S. Michigan Avenue, visit the legendary Chess Records studio, once home to the legendary Chicago-based label that witnessed the recording of blues legends like Willie Dixon, Chuck Berry, and Bo Diddley. This hallowed ground was immortalized by The Rolling Stones in their instrumental track “2120 South Michigan Avenue” during their inaugural U.S. tour in June 1964, paying homage to the studio’s profound influence on the world of music. 

Conclude your night with dinner and live music at Buddy Guy’s Legends and if you are lucky, Buddy Guy himself will take the stage. Sweet home Chicago! 

Day 3: West Town & North Side Vibes

Kick off day 3 with some legit vinyl hunting, at one of the iconic record stores in West Town and Wicker Park: Reckless Records, Shuga Records, and Dusty Groove, to name just a few. 

In the afternoon, make your way up north with a stop at the Old Town School of Folk Music. Founded in 1957, this vibrant institution is a hub of creativity, fostering a sense of community and accessibility to the diverse traditions that shape American and global music.

Looking for more music? The Green Mill is a Chicago jazz institution that has enchanted audiences since 1907. With its intimate setting, historic ambiance, and world-class performances, the Green Mill allows music enthusiasts to be transported through time while enjoying the finest jazz in a setting that has hosted iconic performers for over a century. 

And what better way to conclude your three-day music experience in Chicago than a late night visit to Kingston Mines? This iconic live blues music venue in Lincoln Park never disappoints and is open until the wee hours of the morning! 


Start planning your next getaway at enjoyillinois.com

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