If you had the chance to see Prince perform in front of a crowd of about 300, you would have probably jumped on it no matter the cost. Same goes for The Rolling Stones or The Roots, who occasionally play at some of Chicago’s most intimate live-music venues when they’re in town.
Seeing bands of that caliber in small settings happens rarely, but the opportunity to experience up-and-coming groups occurs all the time in the Windy City. From a punk-rock lounge to an iconic jazz club where Al Capone used to hang out, these venues add color to Chicago’s live-music scene.
Dubbed "the greatest living guitarist" by Eric Clapton, Chicago legend Buddy Guy opened his eponymous downtown live music venue in 1989. Throughout the years, the club has hosted a who's who in show biz: Willie Dixon, Koko Taylor, Otis Rush, Albert Collins, B.B. King, Johnny Winter, Stevie Ray Vaughan, Bo Diddley, Eric Clapton, The Rolling Stones, David Bowie, ZZ Top, Gregg Allman, Slash, John Mayer, Sheila E. and Pete Townshend. The walls document the bar's rich history, featuring autographed photos, endless awards and more. 700 S. Wabash Ave., 312-427-1190
Let’s face it. You don’t go to a live-music venue expecting a decent glass or bottle of wine. You either deal with the crappy wine or order something else. That was the case until City Winery popped up in the West Loop in 2012. With an on-premises wine distillery, the venue cranks out its own superior wine. What it doesn’t offer it ships in from its New York venue. Genres are all over the place as far as music; it ranges from folk to funk. 1200 W. Randolph St., 312-733-9463
The West Loop bar not only gets props because it spotlights the best of punk rock, but also because it doesn’t take its customers for granted. The space is meant to look “divey,” however, it’s clean and loungy with a thoughtful menu of craft beers and pub grub. The venue now features an onsite brewery. 235 N. Ashland Ave., 312-226-6300
Always a popular stop on the gangster tours, the late-night jazz club has been around since the Capone days and served as a speakeasy. In its current state, Green Mill serves up traditional, bebop, improvisational and contemporary jazz nightly to locals as well as visitors, and its after-hours status allows visiting musicians to jam when they’re in town. 4802 N. Broadway, 773-878-5552
For a venue mostly cranking out indie music, Martyrs boasts some of the best acoustics in the city. It’s considered somewhat of an underground gem, taking on less-mainstream, but popular bands playing rock, rockabilly, soul and folk. Every so often, Martyrs will book a big name--which immediately sells out--and among the highlights include Jack Johnson, The Black Keys and The Pretenders. 3855 N. Lincoln Ave., 773-404-9494
As one of the city’s few all-ages concert nightclubs, Metro features a large range of acts, varying from punk to classic rock. Acts on the way to hitting the big time (Kanye West, R.E.M., Smashing Pumpkins) as well as legendary performers (James Brown, Bob Dylan, Iggy Pop, Depeche Mode) have graced the stage since it opened in 1982. 3730 N. Clark St., 773-549-4140
The massive Hyde Park venue doesn't just serve the typical craft cocktails and chef-driven cuisine. Its top-level musical hall books legendary and up-and-coming artists, including the likes of Maceo Parker, De La Soul and Dick Gregory. The team behind this venture also owns Dusek's in Pilsen and Longman & Eagle in Logan Square. 5311 S. Lake Park Avenue West, 312-801-2100
The bustling Lakeview venue is actually three spots in one: the music hall (for which you need tickets), the bar and Harmony Grill. Schubas’ music hall books a lot of under-the-radar bands as well as many groups that go on to stardom such as Janelle Monáe and Wilco. 3129 N. Southport Ave., 773-525-2508
With a rich history dating back to 1892 when it was established by John Dusek, the building housing Thalia Hall/Dusek's/Punch House sat vacant until its current owners brought it back to life in 2013. Its presence has also help re-invigorate Pilsen as an exciting entertainment and dining destination. What also sets Thalia Hall apart from its competitors is that in conjunction with Dusek's, it's the only Michelin-starred restaurant in the United States with a live-music component. Just a few of the major names to grace the stage including The Ting Tings, John Hiatt, Estelle, The Smashing Pumpkins and Dave Chapelle. Tack Room, occupying the former carriage house portion of Thalia Hall, boasts an equine aesthetic and casual back-porch atmosphere that supplements the buildings foremost concepts with piano sing-alongs each weekend. 1807 S. Allport St., 312-526-3851
Another late-night venue, but this one specializes in spotlighting home-grown artists. Passionate blues, jazz, reggae and Latin performers have made Underground Wonder Bar a must-do stop for many famous visiting musicians, including the likes of the Stones and David Byrne. 710 N. Clark St., 312-266-7761