By Marty Rosenbaum

Although the summer is winding down, there’s plenty of time to plan a vacation. Yes, even you procrastinators still have excellent options for a summer getaway.

Summer is the best time of the year for music lovers as outdoor concerts are taking place on a seemingly daily basis in the Chicagoland area. Combine that with the year-round musical offerings the city provides and you won’t need to leave Chicago to have a musical vacation.

However, it’s nice to get away once in a while.

If you’re looking to combine your love of music with a quick weekend getaway, here’s a guide to five cities rich with music that make for a quick weekend trip from Chicago.

Take a look at a few scheduled concerts set to take place in these destinations within the next month as well as must see musical attractions.

While places like Nashville & Minneapolis are great cities for music, we’re keeping this list to destinations drivable in under 6 hours.


Every Thursday night thousands gather in Cathedral Square Park in downtown Milwaukee for free Jazz in the Park concerts featuring jazz, big band, funk, R & B, reggae, blues and other performances.

Also be sure to check out The Exclusive Company, America’s oldest full-line independent record store.


8/27: Indigo Girls at Pabst Theatre
8/31: JD McPherson at The Back Room at Colectivo Coffee
9/8: Conor Oberst at Pabst Theatre
9/9: Ben Harper & The Innocent Criminals at Reed Street Yards
9/12: Taj Majal & Keb Mo’ at Pabst Theatre
9/13: Spoon w/Twin Peaks at Pabst Theatre


If you’re taking a trip with the kids, the Rhythm! Discovery Museum is a must. The interactive percussion museum features a collection of historic artifacts and allows attendees to interact with a wide variety of percussive instruments.


8/19: Kings of Leon w/Nathaniel Rateliff & The Night Sweats at Klipsch Music Center
8/25: Portugal. The Man at The Hi-Fi
9/3: John Mayer w/Dawes at Klipsch Music Center
9/10: U2 w/Beck at Lucas Oil Stadium
9/10: The Mountain Goats at The Vogue Theatre


Detroit’s rich musical history can’t be described within the confines of this article, but here’s a few places all music lovers need to check out during their visit.

Third Man Records
The Motown Museum
Detroit Symphony Orchestra


8/27: Depeche Mode at DTE Energy Music Theatre
9/3: U2 at Ford Field
9/10: J Roddy Walston & the Business at St. Andrews Hall
9/11: Strand Of Oaks at The Loving Touch


A trip to Madison isn’t complete without stopping by the High Noon Saloon. Featuring nightly live music, pizza, and a large selection of beer, it’s everything a music lover needs combined into one place.


8/18: The New Pornographers at Live on King Street
8/24: Twin Peaks
8/30: Bonnie Raitt at Overture Hall
9/3: Jason Isbell at Breese Stevens Field
9/9: Foster The People at Orpheum Theater

Des Moines

Des Moines has an extensive offering of outdoor concerts. Chances are you’ll be able to enjoy live music with the beautiful Des Moines River serving as a backdrop.


8/20: Michael Franti & Spearhead at Simon Estes Riverfront Amphitheater
8/21: Blind Pilot and Gregory Alan Isakov at Simon Estes Riverfront Amphitheater
9/12: Ben Harper & The Innocent Criminals at Hoyt Sherman Place


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