Knowing that I was visiting the city, I wanted to experience a jazz concert. My Mom is confined to…read morea wheelchair and sometimes these gems are not ADA compliant. I spoke with Scott Stegman, the General Manager ahead of time and he was so accommodating and helpful. We had a wonderful time and enjoyed the music, especially the saxophone Thank you for the great experience

We went to Winter's Jazz Club for a Sinatra show, and it was a great time. It's a super cool jazz…read moreclub, and everything that night was set up beautifully, the production, lighting, seating. The set itself was great and really fit the space. I ordered the Blackberry Jam Session, which was great and easy to drink. Service was magnificent throughout the night. Overall, the vibe was excellent, and it felt like a really cool spot. Definitely a great place to catch live jazz and enjoy a drink.

This place has a magical feel IF you're into jazz. If you aren't a jazz lover, you just may become…read moreone here. Well, I love jazz and it's a great place to be. I came here for the first time knowing my grandparents started coming here in the 50's for date night jazz. This place was founded in 1947 and you can see they've preserved this place to keep that same feel with all the greats from the past... Count Basie, Dizzy Gillespie, George Benson, Lonnie Liston Smith, Hugh Masekela, Dexter Gordon, etc. (those are my favorites!). I saw the Kyle Swan Quartet. They were absolutely amazing. You see young and seasoned musicians that are so talented. I usually go to Birdland in NYC but this place, Jazz Showcase, is better to me because it feels more welcoming and like home here versus a production at a theater. We interact with the artists here-- well, they interact with us and make us feel like we are at home and like we are supposed to be there with them, not a performance transaction. $25+ for a show and booking online was a breeze. It's comfortable here, chairs are good and there's sofas in reserved areas but the whole seating area has a great view of the stage no matter where you're sitting. The staff seems gracious and kind of everyone who visits and genuinely wants you to have a great time. They see very selective in their talent that performs here... but why wouldn't they when they've been here for so long and had the best artists perform here?! I came the night that The only downside that may be for some people is they don't have food... only drinks. Me personally, I ate before and don't come for food, I come for the jazz... but they've got beer, cocktails, and other spirits. Macallan and Laphroaig for those who need a good whiskey. Come here if you're ready to relax and listen to great jazz with artists who know their craft. I'm coming back with friends... or even alone. Yeah, it's cool like that. ***Side note: the GPS may take you to the Main Street and you may not see the sign right away and actually have to turn the corner on Plymouth and walk down that side street to get to the end of the block (where the dead end/no outlet is).

Great time! The performance was really good and the venue was huge! Random comfortable seats in the…read moreform of chairs, sofas, couches, and loveseats. A little on the expensive side for a one hour show! Shocked that a complementary drink was not included in the fee.

We had a great time, band was good, but the icing on the cake was Buddy Guy himself coming in to…read moreperform. We got to see the legend in action and he didn't disappoint!! Our waitress was attentive and refilled our drinks as necessary.

I always wanted to come and visit The Legendary Buddy Guy's for a night of Jazz. This particular…read morenight Toronzo Cannon was getting married at Buddy Guy's & after will be performing. I got there early to get a good seat close to the stage. It was a packed out night. Grown Vibes and some of the best performances. I enjoyed the atmosphere and show. The flip side is the service & food sucked. The server Katarzyna was rude and unprofessional. I understand it was crowded that night and service was slow. It was the attitude and demeanor and rudeness. The staff also seemed to be unorganized and unprepared on that night. I ordered the fish and chip and it was greasy and very salty. I did enjoy the performance of Toronzo. But, disappointed with the service and food.

Lovely spot for jazz. The customer service was amazing from start to finish. Everyone was genuinely…read morekind, from the moment you walk in and pay the cover charge to the server who went out of their way to make you feel comfortable and stayed very attentive throughout the night. The music itself was also really good and felt like the main focus of the whole experience. If you are solo, there are not always the best views of the stage depending on where you sit, but it still felt worth it because the performance is strong enough that you stay engaged no matter where you are seated. They ask that conversation volume be kept to a minimum for the performers. The food was decent and a little pricey, but for the overall experience it felt worth spending a bit more. Between the atmosphere, service, and music, it added to the night rather than taking away from it. Overall the combination of great customer service, good energy, and the location near the riverfront made it a really enjoyable experience! I was also able to walk from my accommodation to the venue and back, and it felt safe and easy to navigate.

Great spot to enjoy a night. Food was good too. We enjoyed…read morevisiting with others around us and it was just relaxing while filling our brains with jazz. I wished there was some swag to buy as my husband's name is Andy. But that's okay.

Just wanted a place to stop in for drinks for an hour or so. It's setup like a speakeasy so there's…read morea cool way to enter the place. Great service! Great atmosphere. Good drinks. The only thing negative is they charged us a cover fee for entrance on a Friday during Happy Hour which we later discovered should have been free admission based on the advertisement on the bar's flat screens.

Visited on Saturday night, 6/13. Rudest bouncer I have ever encountered. Ran into a hiccup with our…read morereservation and rather than helping our large group he stonewalled us. Another employee helped us out and was great. Would not return if this bouncer represents your brand.

I have been to the Chicago Theatre several times for concerts and have had experiences in all of my…read morevisits. It's an iconic Chicago landmark for catching live events. I like its ornate décor, the stadium style seats set-up which offers good stage view, the acoustics, and the overall aesthetics of this venue which makes it an ideal place to watch live events. On my recent (late June 2026) visit to see The Human League, Soft Cell, and Alison Moyet for the Generations tour, overall, I had a good experience. There were couple of issues that we had such as lack of cool air circulation inside the auditorium (it was hot and sweaty) and a couple of people standing throughout the show to dance, blatantly blocking other peoples' view and not caring about being inconsiderate and uncourteous to people behind them to which the theatre ushers had no problem with it. Otherwise, I have not had issues at this venue. So, 4.5 stars but rounded up to five. I look forward to going back here.

Beautiful building, been here for several performances. Friendly staff. Usually use SpotHero to…read morefind a decent priced parking nearby. Holds about 3,500 people I believe, so the lines for drinks etc can get very crowded. The trick for entry is to use the side entrance which has 3 security lines and moves fairly quickly.

(Kari's Rating 8.5/10)…read more Stopped in for a quick drink before dinner before Gus' Sip N Dip. We didn't have much time, but it was of course dead as it was 7 PM on a Monday. I ordered the lemon drop martini and it came with a beautiful sugar rim and a curly lemon slice which made the drink look very aesthetically pleasing. It is relatively loud because it is a semi-karaoke bar. The bartender was really sweet and made our drink relatively strong. I loved coming here when it's super busy for a happy hour or a late night piano session.

10/10 amazing time. All of the musicians are extremely talented. They all switched between…read moreplaying piano, drums, bass and guitar in addition to singing. And they played for hours!! The mix of music makes it fun for everyone - Get Low, Come on Eileen, Pink Pony Club, Billie Jean, Como La Flor. My friend said she didn't realize she was coming to a concert. The food is good but the drinks are a little weak, still good though. Howl at the Moon is great for all ages. You will definitely enjoy it.

My friends and I went to Chicago for a girls' trip and discovered Redhead our first night. Kaleen…read moreDolan was playing piano that night and was so amazing that we kept going back all weekend! Her energy is amazing and she is so interactive with the crowd. We were all in awe of how talented she is at singing (absolutely anything!) and playing the piano!!

If you're looking for a great night out in River North, Redhead Piano Bar is always a solid choice…read more Kaleen Dolan and Michelle have this place moving like a well oiled machine between the music and keeping drinks moving! It has that classic Chicago piano bar feel -- lively but comfortable, energetic without being overwhelming. From the moment you walk in, you can feel the fun atmosphere. The lighting, the music, and the mix of people all come together to create a really welcoming vibe. The staff truly adds to the experience. Everyone is friendly and attentive, and you never feel overlooked. A special shoutout to Michelle, who goes above and beyond to make sure guests are taken care of. She's warm, professional, and genuinely makes you feel welcome, which makes a big difference on a busy night. Of course, the highlight is the live music. The performers are incredibly talented and know how to read the room, keeping the energy up while still creating moments where you can sit back and enjoy the music. Kaleen Dolan is especially impressive -- an amazing musician with a great voice and presence. She connects with the crowd effortlessly and makes every set feel personal and engaging. Whether you're out with friends, on a date, or just stopping in for a drink and some live music, Redhead Piano Bar consistently delivers a fun, memorable experience. Take it from the #1 Steve - this place is TOP SHELF fun!!