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Best Jazz Clubs in Downtown Chicago: Top Picks for Blues and Entertainment

Chicago History, Downtown Chicago, Roaring 20s

When you’ve got the blues in downtown Chicago, there’s no better pick-me-up than an evening at a jazz club-and martini in hand! Chicago offers some of the most interesting and unique jazz clubs in the Midwest, places to enjoy the soulful stirrings of Buddy Guy, swing to Ray Brown, or just become a jazz aficionado. Many of Chicago’s popular jazz clubs grew out of the Prohibition era, the roaring ’20s that piqued interested minds and music tastes of hundreds of jazz musicians and area artists. Sit back and enjoy the show; it’s a Chicago opportunity you don’t want to miss! Here are just a few of the best jazz clubs in downtown Chicago:

Joe Segal wasn’t wrong when he picked the Jazz Showcase at 59 W. Grand Avenue for some fo the area’s top shows. This lounge is decked out in mahogany and black décor, and the full bar menu will keep you busy int the late night hours. The Dinner Package is a great option to enjoy some classic Italian before a reserved table at the showcase. Daily features include local musicians and guest stars throughout the year. Sunday matinees draw students, aspiring musicians, and Institute of Chicago members for a little variety. Call (312) 670-BIRD for your reservation.

It might be the super-casual atmosphere, or just the feel-good vibes that resonate from the New Apartment Lounge as you walk past 504 E. 75th Street; whatever the case may be, this is a classic Chicago venue that continues to draw jazz fans and enthusiasts of all ages and backgrounds. Open from 1 p.m. to bar time all week long, you don’t want to miss the showcase of local and national talent. The drinks are served in generous proportions, and you can’t ever complain about a dull atmosphere at this legendary tavern. Cal (773) 483-7728 for more information.

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Where else can you enjoy a dish of classic pig’s feet than the Checkerboard Lounge? Located at 423 East 43rd Street, this is the spot where Junior Wells generated local interest for jazz in full force. Walk into a relaxing and cozy setting amongst the wood and bistro-style chairs, and you’ll be ready for the evening with the soulful sounds of your favorite blues artists. If you’re up for a card game or two, stake a claim at one of the booth-style tables in the back! Call (773) 624-3240 for more information.

Blue Chicago is the place to find a variety of shows with female leads only; this is the place to enjoy a relaxing but exciting evening with a strong lineup of talented artists. The oversized stage is perfectly centered opposite the oversized bar. You’ll find yourself nestled in between some comfy wooden chairs for a view of both! If this atmosphere doesn’t suit you, head over to the sister location at 736 N. Clark (just down the street from this location at 536 N. Clark). Call (312) 642-6261 for show schedules and hours.

One of the most respected jazz clubs in the area is Andy’s Jazz Club; there’s never a dull night here. Located at 11 E. Hubbard Street, this is the place to browse the Wall of Fame as you sip your cocktail across the bar, and enjoy the 30-year establishment’s roots in Chicago history. The lineup of nightly live shows includes a Friday afternoon performance at noon. Where else can you take a midday break with some soothing jazz sounds and great atmosphere? Call (312) 642-6805 for more information.

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When its jazz and blues you’re after in downtown Chicago, be make your selection at Chicago’s finest. From casual and laid back to dressy and upscale, there’s something for all tastes in downtown Chicago. Ray Charles and Junior Wells would be proud to call any of these lounges their hotspot for the night. Enjoy your evening of jazz and cocktails after you’re done trekking through Michigan Avenue; you’ll be setting yourself up for an entertaining night to remember in downtown Chicago!