SO SO GOOD!!! My friend and I went on Friday and loved it so much that we went back again on Saturday - we weren’t the only ones, it turned out, as we saw a lot of the same people there coming back for more. We were there for Laura Cai and she was absolutely incredible. So much joy was had, singing and dancing all night, lots of camaraderie. Door staff are very nice too and the cocktails were delicious (we just had Sonya’s Peaches the whole time bc they were so good).Highly recommend! I’ll be going again next time I’m in the city. Stays open so late too and we couldn’t tear ourselves away!

We had the bast time there on Sunday night! We got there around 9 and it was a blast. Not too busy, not too crowded but the music is what we came here for. We went back again on Tuesday, still fun but I think the lady on Sunday evening was a blast. Can’t wait to go back.

Outside we were told that men were not allowed to wear hats inside, and that the majority of the people inside were dressed in formal wear. However at the door, a woman leaving was in athleisure (hoodie and leggings), and the rest of the crowd was in what at best could be described as COVID business casual. If there is a rule about the dress code, make sure that it is enforced with all patrons instead of the ones the bouncer in the sunken place deems fit.

Come early to grab the seat you want. We came here after dinner next door. It was right before 8 and we grabbed a seat in front of the bar and can see the stage. The drinks were good but a little pricey for a dive like bar. The pianist was Kathleen Dolan and she was amazing! She was really good and we enjoyed her show. When we left at 10 there was a huge line. Due to Covid there was no standing room (in April). Not sure now.

Such a fun place to potentially have fun, but the paino guys (especially Dario) are on such a personal trip to sing long & hard and market for tips….that you lost me at the first awesome Journey song— after I had tipped him $20 bucks twice. I wanted it to be such the classic experience as in the years past…but miserable because of the blown out speakers. Ego trip at its finest. Miss the Piano Bar.None of the kids at 12:30 am were passing tips to the piano guy. At all.

LOVE this place. Always a great time: live piano players after 8, singing, requesting the best songs. For those who wish: there is a cigar bar attached for enjoyment.I recommend coming early to avoid a line (especially with covid restrictions).I wish their beer selection was more expansive, but they have Stella, which is a great option.Can’t wait to return!

I am an event planner and took a group of 25 women here for a corporate retreat and let me tell you, they had the most amazing time!! We worked with Kenzie and she took care of every little detail. She was very communicative, onsite to greet us, made sure everyone had what they needed. And she was kind, professional and so hospitable. I highly recommend working with their management team to arrange private seating for large groups. This was the highlight of the trip!

After a day of sightseeing, I wanted to get some drinks with my husband. We were staying on the Magnificent Mile and this place was close to our hotel, so decided to go before turning in for the night. We were greeted by a doorman that shined a flashlight on us up and down who did not let us in due to not meeting dress code. That part was embarrassing. I will give him this, at least he said it nice but I was surprised. I had on a sundress and my husband had on shorts and sneakers...typical summer attire when its 90 degrees out. I saw no signs in reference to dress code, but did not fight this and moved on. I get ambience and wanting to create atmosphere, so this was the choice of this establishment. We packed nicer clothes but really didnt feel like going back and changing just for a few drinks. I came from an older generation where you dress to go out, but these days people really dont anymore. The art of dressing up, although appreciated, is somewhat a dying form with the new generation. Even at nicer restaurants on our trip, my cocktail dress and husbands dress shirt and tie attired seemed out of place on this trip (compared to other patrons at those places) so we were surprised we were denied at a piano bar for a few drinks. Lets do the math....average drink is about $20 in this area of Chicago. We would have each had 2 or 3...then the 20% tip on top of that. So low estimate of this place missing out on $100 for 2 drinks each with tip...just because my husband is in shorts and sneakers? Thats fine. An upscale bar within walking distance to our hotel welcomed us in casual attire right away and gladly took our money.

This is a classic. If youre even reading this you have to go. The bouncers outside fancy themselves very serious. As soon as you get in you will have a great time if you like to sing along and meet friendly people!

I had one hell of an evening there. The staff is AMAZING. Super courteous and helpful. The bar looks good and the ambiance was top notch. The piano guy was super entertaining. We went and had a cigar, the selection was great and the crowd in the smoking area was super friendly and chill. Great place, we loved it, we want to go back.

Fun place to unwind and sing along to your favorite piano tunes! They also have a huge walk in humidor and a cigar lounge upstairs with the piano player streaming to it.

Its nothing more than a dive bar trying to masquerade as a high end swanky venue. The bouncers are the complete opposite of who youd want to be the first person a potential customer talks to when they come visit your business. They are rude, impersonal, and make it obvious that they are just looking for you to slip them some cash to let you in.Dont bother, there are plenty of other great places within walking distance.

This place is a gem! Michelle and Bri are amazing bartenders and super attentive. Robert at the door was magnificent, A stop here is a MUST when in Chicago! The musicians were so spot on and knew EVERY song. Group karaoke like non other

One of the best bars in Chicago! So good and reasonable priced! A+

Good bar, very relaxed. I used to go before the pandemic. Was denied access due to not being vaccinated regardless of wearing a mask. Not upset, just thought others should be aware.

Awful place to waste an evening. Spend 20 minutes walking there and get told you arent dressed up to their code. As if they have enough guests to afford filtering out paying customers. I had a t-shirt, shorts, and tennis shoes. Sorry but I thought it was 90 degrees outside and I had a 20 minute walk. So if you guys want to get blisters and soaked in sweat before you arrive then feel free to show up in your fancy clothing and theyll let you in. I dont know who you would be trying to impress, but thats your business and apparently theirs too.

This bar is the best in Chicago. It is historic but not only that, accommodating and welcoming. Last but not least, when you go here - ask for the Bartendress breanna! She is the best old fashioned Bartendress in Chicago. Tell her Mack and Emma sent you ❤️

This was a great little find. Very classy interior with a great vibe. The complimentary coat check was very nice. The piano playing and crowd that followed made for a great environment. The best part had to be the humidor and cigar patio off the back. This really sealed the deal for my wife and I as we are occasional cigar smokers.

Loved my first visit! The atmosphere is incredible, and the perfect setting to celebrate re-opening since COVID. Service and drinks were amazing, along with the UNBELIEVABLE talent they have - Lauren Hall was absolutely incredible! Looking forward to going back soon!

Nice little cigar selection. Service was top-notch. Clarissa, Stephanie and Dan take great care of you!!

Yassss Breanna is THE best server you could wish for🎉 so glad we came, plus water

Kareem Dolan is an absolutely delight and insanely talented. She can play nearly anything you can think of as though she’s been practicing it on the piano for years and does so with personality! Such a fun venue after dinner to drink whisky and beer while having a great time. I will definitely be back

Place is ok kinda dark. Fun pianist.

Originally I wasn’t enthused when my husband initially suggested this place. But finding a place to buy and smoke cigars but also to order cocktails in Chicago is quite the challenge! In the pics posted in Google reviews, clearly they’re old pics. I thought this was an old school, sleepy spot and I couldn’t have been more wrong! They clearly have gone thru a facelift and on a Saturday night, it was packed!  They had a “walk-in humidor” with a great selection of cigars and a cute outdoor, well ventilated lounge with monitors and sound system so you could hear the live piano music. Brilliant!

Wonderful place for a drink with live music and a nice cigar humidor! You cant go wrong with this place. Reservations are recommended and being vaxed is good.

This place is very gloomy and made us tired. It is also really over priced. The staff was polite.

Loved David on the piano. He even brought out the harmonica to play Piano Man! Cocktails are $14 each but that’s average for downtown Chicago

This is one of the best bars in Chicago for live music on a weekday night. The ambience is amazing and makes you unwind from work stress. We are regular visitors here - Kaleen and Rachel have been awesome on the piano!! Definitely recommend for locals and tourists visiting Chicago

Got kicked out for wearing reasonable attire. The place really isnt nice enough for a dresscode, and theres pictures on here of people in there dressed casually, so....?

This is my go-to place! Everything about the Aesthetic is something I would suggest to my family and friends. A phenomenal place to bring family OR friends. I suggest Red Head to anyone. I have been around urge city for years and this is my favorite place to have F-U-N.

Rasist attention with the Latino people in the gate

Stu, the piano man, is awesome!! He is funny, engages the crowd, and is incredibly entertaining. I didnt give 5 stars because we felt the service couldve been better. The one waitress we had was slow in getting us drinks and had to confirm our order several times before getting it right. We ended up leaving the table and getting drinks from the bar instead. Overall I would recommend.

Had a blast... Bartender, Sam was the best!! The Performer was great too!! A little pricey but worth the visit.

Great live music venue with amazing staff. Always a fun time

Very entertaining, the crowd control is a little over bearing. Everybody gets the covid restrictions, but I didnt like being time to sit down while were singing happy birthday to my companion. That was a much

Always a local fun favorite. Piano bar with classic music, lounge upstairs for cigars plus speciality drinks. Either call to reserve or get there before 6pm to grab a table. It will be pack at nights. #localspot #romantic #happyhour #tridence

Great place to go has a wonderful staff from the gentleman at the front door to Brianna the bartender was so nice and fun. Lauren Hall was the amazing entertainment at the piano . Will definitely go again and highly recommend.

I ordered my beer and the the bartender gave me six beers which I said no problem Ill pay for them. I handed them out to people around me. The bouncer said I was causing trouble and told me I had to leave. I do not recommend going to this place its a scam.

Perfect staff, place, and service to spend a memorial time. Loved it

It’s very old school “gentleman’s club”. If you don’t want that vibe, be prepared to get kicked out for defending yourself. They won’t ask questions, they’ll only defend who’s paying the higher tab.

Love this sneaky spot.good to smoke a cigar out back. Speakeasy style place

So happy The Redhead Piano bar is open again! This has been a staple of ours for many years. A Chicago landmark. Rachel was playing last nite, she was fantastic! She had a great array of songs and engaged the guests. We got there at 8:15 last nite. We got the last two seats at the bar and then a line started to form outside. They have a cigar bar as well. So much fun and the host, Eddie was very welcoming. A must visit for us every time we’re in Chicago!!

I waited 45 mins in line for myself and 2 friends. After waiting that long I was informed I could only get a spot for me, unless your party is all in the long line together. If they wait 45 more mins, they cannot sit with you.This might have been understandable if I didnt watch 3 bribes pass me. I mean, cool. I felt like I was on Tv. Just some loser with only enough money to buy a bunch of drinks and tip well.Not vague, not inconclusive, just sure, if you tip me enough. If you are not rich, downtown you are irrelevant.

Bunch of rude hood guys standing at the door, and they treating people (who are thousand times at a better place in life than them) rude and bossing them to satisfy their egos so that they can feel good about their miserable lives. I would not spend a dime here nor step foot.

A Chicago staple! If you’re looking for a fun time out you’ll find it here. The walk-in humidor is always chock full of cigars(also has a smoking patio out back)

Absolutely the best place for entertainment in Chicago!!Must go for Dario on Saturday nights. That guy can play the ivory off the keys!LOVE the drinks, the staff, the vibe.

Loved it. Went here twice while in town and met great people in the back patio both nights. Drinks are slow. I think it was a function of small bar and lots of people. They were good and the wait staff was friendly. 5* because I had a great time two days in a row. Will go back next time in town.

Cute lil piano bar where they actually play the songs you request! They have a cigar lounge outback which is so comfy. Great service and friendly staff. Highly recommend.

This was a great bar. Our bartender Adam was awesome. We were celebrating our 10th anniversary and requested our wedding song which was played. Hung out for hours.

Ill be honest I was expecting more from this place. Well start with what wasnt good which was the service at the bar. my drink was empty for about half the time I was there and by the time they finally got around to asking to refill it I was already over it and wanted to leave. however what was great was the piano music what a fun time. Also people watching in this place is fantastic. Ill probably give it another shot just to see if a different bartender makes it all better.

Nice place, humidor is small but the atmosphere is really chill.

Fun, local, great beer. Seriously, what more do you want in a place? Tucked back in a neighborhood that gives it a laid back and easy atmosphere. Owners are friendly and staff is knowledgeable. If you havent been here, why not?

Great service and patio for cigar smoking. Talented performers and servers. 2nd kitchen food delivery and food prices.

It is a good place to listen to the piano, but there are too many people on the weekend.

It is a piano bar which I have known since 1994. There is always nice crowd and music, it is highly recommended

What a cool little place. Stumble upon this place by accident and was amazed. Small cozy place with a horseshoe bar. Dim lights and a piano man. They also have a cigar room. This place is straight out of a Hollywood film.

Fun place to have a drink. Just be prepared to wear non street shoes or t-shirts. My friend was wearing black sneakers and they made her rent a pair of black flats and wear a Jean jacket over her t-shirt.

Purposely kept us outside to create the perception of a line. Otherwise typical downtown bar and really the only location you can find live music during the weekday, at-the-moment.

This is the first two star rating I am giving. We were a party of 4 and asked some locals for a place to watch live music. Someone suggested Redhead Piano Bar. Upon arrival, as advertised, there was live music. We sat at a table and were presented drinks menus.However, there were no prices!? We called the waitress over and asked here as to the pricing and here answer was “it varies”. Now as a tourist spending foreign currency this is simply unacceptable as it is a recipe for disaster and a quick way to get taken advantage of. It is honesty the first time in my global travels that I have been presented a menu with no pricing. We promptly got up and left.

An oldie but a goodie

Great venue with talented artists! Friendly and fun outgoing staff! Great cigar humidor and outdoor smoking lounge! Definitely order an old fashioned cocktail!! The vibes are great and the atmosphere is fun! Drink. Dance. And enjoy a fun night out at a late night establishment to keep you coming back! :)

It took forever to get in, and it was pretty pricey. Good tunes tho, they have a great musician at the head of it all.

Great music and ambience. 😃

This bar was cool the pianist was entertaining and service was pretty good. I will visit again

Good vibe and atmosphere at the place...also the doorman is also very friendly. Highly recommend this place.

Great crowd, and equally awesome music. I am an Old Fashioned snob and theirs is pretty good, enjoy

Fun little dive bar kind of atmosphere. A hidden gem with a cigar bar and an enclosed patio for smoking. Drinks are wet and not too expensive. The piano player was a hoot - she must have gone 3 hours with only one small break. Its no high class hangout, but its got a down-to-earth kind of feel.

Amazing singers. The best staff

Excellent entertainment venue! Had such a great time there. Kaleen is incredibly talented and entertaining with her wit and personality. And KYLE with his continual requests for sad songs made the evening interesting!!! Highly recommend. WARNING: This place may be addictive...

I have been to most of the piano bars in Chicago since living here and redhead by far is the best. I was there on 10.15.19 and they had a new singer named Rachel and she was amazing. Any song we wanted to hear she played and she made it so much fun. Definitely would love to know what days she will be playing so when I have friends and family come into town they can also see her play. Great job redhead I love this little spot!

I miss this place so much! Classiest staff around and they know how to make a stiff Manhattan on the rocks

Great place for a drink, or more😜Loved the atmosphere and live music.

Nice bartenders and great live music!

Loved going there! The singer and piano player were simply wonderful! He took song requests. The place was packed with all age groups (above 21 of course). They have a cigar room. No cover charges. The only reason I am giving this place 4 stars is our waitress. We didnt know how the place operated so I went and took a seat and my husband ordered drinks at the bar. The waitress came and said we have to close the tab and open a new one so that she can attend to us. It was fine with us. But when I am on a night out I dont want to listen to your policies and jiber jaber. I am doing what you are saying, you dont have to show your frustration to me. She started saying that people tell her it doesnt make any sense, but the tables are hers. Its fine! Everything is fine as long as you are doing your job diligently which she didnt. We waited for a long time and then a lot of excuses.

Good fun on a Saturday night. Live music, singalong, good service, nice crowd.

Amazing. It was mu friend’s and mine first time there and everything was spot on. From guy on the piano (HUGE BENEFICIAL FACTOR) to staff friendliness. This place is a true American bar like You see on movies, only better!! Check it out, loved it - recommend it!!!!!

Fun atmosphere! Cigar lounge is nice. Get here early if you want a seat. Great place for couples and groups. Mules are tasty but expensive. Took too long to get a beer. Id go back.

This place always is fun. Excellent staff, fair drink prices, and fun people watching. If youre female, youll get some attention. Lot of business travellers that are looking for fun. Just say No thanks, or enjoy the flattery & the moment.

Always a great time at the Redhead Piano Bar! Staff are friendly and good for a laugh. Place has an excellent selection in their humidor, and a swanky little patio to enjoy a drink and a smoke on. Kaleen is my favorite pianist so you’ll definitely want to catch her playing.

They play my favorite song everytime, Its raining man.

Not a big place but ambient and drinks are that good to keep the place always full packed. Expect to make a line of 5 to 10 minutes.

An electric piano, cramped, and loud..

Accessible cigar bar is the reason for this 5 star review. This bar is one of few cigar bar that does not have cover charge or entry fee. They have a walk in humidor with some basic essential cigars. Good for beginner. Or you can bring your own cigar and smoke without additional charges. The cigar smoking patio is heated and comfortable. Alcohol selection is ok.

This place is amazing! Solid performances. Space is big enough so you can get close to the piano player or chill towards the back

Great service and amazing music.

Amazing! Great drinks, have there own humidifier with LARGE selection of cigars. Everyone is really friendly and welcoming. Live piano music throughout the night and they are open late (4am). I will be going back! Try the Red Head, mixed very well. Classy environment but you wont be shamed if youre not dressed to impress

The only lounge in Chicago where you can smoke a cigar. Granted it is a cold room but who cares. The bar is great with an attractive crowd. Live piano with singer taking requests. A very enjoyable time with nice staff.

This place was a blast. I expected it to be just another piano bar. We were lucky enough to catch Kaleen Dolan on a Friday night (she plays Friday and Sunday nights). She’s a spectacular musician and performer. We had such an amazing night and ended up staying until the end of her performance. Can’t wait to go back.Drinks were good and priced well relative to River North. Service was good.

Ok... whoever this new girl Rachel is?!?! She is the ultimate package! This is my second time to Red Head and this time around was absolute delight! After my first time here I wasn’t sold on coming back, now I only wanna come back when Rachel is performing! I am telling all my friends about her and to come to Red Head. So much fun!!!

WOW! This place is amazing! Live entertainment and great atmosphere... People singing along enjoying a drink with friends. Just a great place to grab a few drinks.Oh and the bartenders are incredible! Sharp and professional.

Awesome place to enjoy Chicago night life! They have live piano music, and cozy seating. Always a packed house each time I have visited. Their smoking room has a chandelier! A must stop for every trip to the windy city.

This place is absolutely amazing. Cocktails were fantastic. The atmosphere its energetic. The entertainment phenomenal. This is a must if youre in Chicago!

The quality of musicians can vary from night to night, but this is a great bar with a nice divey vibe and is the kind of place where you sing with the songs rather than listening in silence. The drinks are on the expensive side but there is no cover -- most live music venues in the area charge $10-$15+.I dont smoke so I cant comment on the cigar component other than to say it is invisible if you dont go to that area (the bar is completely smoke free).

Wonderful little place, very eclectic crowd of varying ages. Great live music, friendly staff, and one of best spots for a scotch and a cigar after work. Definitely recommend

Cool place

Love it here! A wide variety of musicians make each nights experience different. New promotions highlighting wines, martinis, and cigars offer something for everyone. And a new partnership menu offering food from the Chop House means we can stay longer, drink more, and enjoy some live music. If youre a local who has never visited, add them to one of your nightly around town places. If youre from out of town, be thissure to stop in at this historic, fun, dont-want-to-miss-it Chicago hot spot!

A great piano bar spot. You can make requests to be played. Lively crowd, seems to be a local favourite

I was in town for a conference. A friend and I decided to get a cigar and this bar popped up.The Bad:There is no food and the cigar smoking is on an outside patio.The Good:Nice selection of cigars in the beautiful humidor. The staff is very friendly. Eva was our server and she was a delight.The crowd was great for a Thursday night. I will say that s scan of the area looked like 4:1 ratio of attractive ladies to men.

This place was so much fun! Highly recommend! The pianist was amazing and took all of our recommendations. Our servers were quick and attentive, always making sure we had everything we needed. Will definitely be back!

I go to red head because they make a great old fashioned and are open late. Frankly piano bars are not really my thing. I appreciate the musicianship of the performers but the crowd shout singing off key isnt for me. If you like to sing along this place is for you.