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    The Water Hole Chicago

    4.1 (26 reviews)
    Open 4:00 pm - 2:00 am (Next day)

    The Water Hole Chicago Photos

    THE WATER HOLE CHICAGO ATMOSPHERE

    What's the vibe?
    Moderate noise
    Live music
    Divey
    Good for dancing

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    Back room where the music's happenin'.
    Lola K P.

    Visited Fri night several times to watch a friend play, and we really enjoy this place. Can't be beat for being a great dive joint with live blues, warm friendly people that make you feel like family. Very informal and comfortable atmosphere, not too loud, no one's shushing you if you talk, but why would you? Mary Lane and her band are entertaining, and it's really fun when she invites guests up (lotta musicians there, and they all know each other.) The regulars are a trip! Mr. Sat. Night DJ, you da bomb. We'll have to drop by to hear what you're spinning. It's split into two rooms, bar in front, and music in the back room with another bar. You can order fried chicken or catfish, comes with fries and a slice of white bread. Cook is very tall - and funny.

    Larry Taylor belts the blues in 2016 at the Water Hole, with the late Killer Ray Allison and his band.
    Bonni M.

    The Water Hole is still open! Good place several nights a week to hear blues music and jazz. The waitresses are very hospitable to people inside and outside the neighborhood. Larry Taylor played there in 2016 and this year Tail Dragger and Elmo James Jr. have been playing. They have a great blues jam with Lori Lewis on Wednesday nights. Tony, a retired cop, rents out the place for private parties on Saturday nights.

    Waterhole sign
    Jacqueline S.

    The Water Hole is a neighborhood favorite for meeting friends and watching sports on TV at the bar and for incredible live blues. Can't say enough about the talent on stage Friday nights. The owner Piece of Cake makes the place feel like home.

    Always happening at this juke joint!
    Mj B.

    Great atmosphere, great music..Tonight blues sensation Tail Dagger In the building August 7th 2018...show starts at 830pm

    Eizabeth K.

    Worst experience at a bar I've ever had. Took a sip and thought I noticed something.. poured it out into another glass and well... I'll just leave this here. Not one bug but.....absolutely disgusted

    KATIE L.

    a great place to hang out. reminds me of chances r, just no peanuts to throw on the floor, great music , food and fun. live blues some nights, comedy others, darts and bid whist. always ask about drinks speicals, you don't ask, you may miss out. grown ass fun for grown ass people. ps. i heard thid place will be a part of the chicago blues tours. kk.

    Long Island! Not for the faint of heart!

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    12 years ago

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    2 years ago

    I asked the bartender the prices of the liquors & she said she didn't know. Go ask one of the customers. lol

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    11 years ago

    I didn't like the drink I ordered, but their food is really good. Nice place to go after work. They also have slot machines.

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    10 years ago

    Awesome place. Easy going. Cheap drinks. Good service. What else can you ask for in a corner bar?

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    9 years ago

    Truly one of a kind..One of Chicagos only true Juke Joints. Everyone there has always made me feel welcome.

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    11 years ago

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    Ask the Community - The Water Hole Chicago

    Review Highlights - The Water Hole Chicago

    The Water Hole Lounge is an Awesome Bar to get away and think, or chill with a group!

    Mentioned in 2 reviews

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    Jazz Showcase

    Jazz Showcase

    4.4
    (236 reviews)
    3.0 mi
    $$

    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.

    Photos
    Enjoying drinks while waiting for the performance
    Enjoying drinks while waiting for the performance
    Jazz Showcase
    Omar Sosa performing

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    Omar Sosa performing
    Rosa's Lounge

    Rosa's Lounge

    4.6
    (174 reviews)
    4.0 mi
    $$

    We had a great time at Rosa's. Great venue for the blues. Brought a couple of slices of pizza and…read moretheir beer was cold. Cocktails looked good, the band was great.

    Great intimate blues venue with street parking. A hidden gem, located on Armitage.....Think, dive…read morebar with live music. The bartenders and hostess were very friendly. We were meeting some people and since seating was limited, tables had to be reserved. We were all seated together, close to the stage at a table reserved for us. The bar was sufficient but they may or may not have your specific drink. But there were definitely enough adjacent choices to satisfy. They accepted all forms of payment, except checks........There was a sign that actually said it..........I thought it was funny. No food but you can have food delivered. The Stephen Hull experience was the show we attended. The show was phenomenal. We were sitting close to the stage, so the music may be too loud for some. There were people wearing earplugs but personally, I was fine without them. It was Stephen Hull's birthday, so staying consistent with that theme, he celebrated. We left at intermission but they live streamed the entire set on YouTube....Great time....We're looking forward to returning soon.

    Photos
    Exterior of Rosa's on Armitage
    Exterior of Rosa's on Armitage
    Rosa's Lounge.  3420 W Armitage Ave, Chicago, IL  Old Chicago Live Jazz & Blues Lounge. Cool!
    Rosa's Lounge. 3420 W Armitage Ave, Chicago, IL Old Chicago Live Jazz & Blues Lounge. Cool!
    Rosa's Lounge.  3420 W Armitage Ave, Chicago, IL  Old Chicago Live Jazz & Blues Lounge. Cool!

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    Rosa's Lounge. 3420 W Armitage Ave, Chicago, IL Old Chicago Live Jazz & Blues Lounge. Cool!
    Andy's Jazz Club

    Andy's Jazz Club

    3.7
    (706 reviews)
    3.6 mi
    $$

    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.

    Photos
    Sabertooth takes the stage on a Thursday night.
    Sabertooth takes the stage on a Thursday night.
    Old Fashioned.
    Old Fashioned.
    View of stage from my table

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    View of stage from my table
    Bordel

    Bordel

    3.6
    (287 reviews)
    2.9 mi
    $$$

    Came here for less than 10 minutes. Ordered a single drink that I took two sips of. I signed for…read more$20.91 for said ONE drink after their 18.88% surcharge that they allege (Bordel) keeps their business fully staffed, give healthcare benefits, and a livable wage. BUT somehow Chey S. Still decided to alter my receipt and give her a $10 tip. Which I did not give her. To which is also illegal. If this surcharge that they claim allows for them to take care of their employees - then why are they stealing from their customers? Anyone who comes here or has been here- take pictures of your receipts after you've signed and totaled them. I see in the reviews Chey S. Is a commonly denominator in bad reviews. Not sure why she's still employed here. Committing crimes and businesses letting it slide isn't a good look. Still waiting on my refund of $10 for that check 72 from Thursday the 23rd at 11:39pm that I have yet to receive! Idc to pay the $20 for one mediocre drink, but stealing is completely unacceptable. And it being excused even more so. Unfortunately I don't live in Chicago or I would've filed a police report, since this is FRAUD AND THEFT. Just beware of anyone who visits. I SIGNED to pay $20.91 not $30.91. There was a big fat ZERO tip for a reason. SO for check #72, I'll be waiting for that refund.

    My friend and I stumbled upon this place while looking for something to eat. While they did not…read morehave any food, this place is absolutely a great time. We had no idea what we were walking into but I am so glad we decided to check it out. They play a vast variety of music and have live entertainment. Our bartender was so sweet and made sure everyone was able to place their drink orders despite having a packed bar. I will definitely be back and hopefully get a table the next time around to avoid awkwardly standing in front of the DJ lol

    Photos
    Bordel
    Bordel
    Such a vibe.
    Such a vibe.
    Bordel

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    Pequod's Pizza

    Pequod's Pizza

    3.9
    (8.9k reviews)
    4.2 mi
    $$

    GET A REZYYY!!! I'm not from Chicago. When I come to visit…read morethis is my fave place! This pizza is super cheesy, we made our own! They serve it for you and show you the cheese, the cheese is on the crust as a well like flaked. They have a two story. Pepsi products -not my fave. They have a bar as well on both floors. We had to wait for our server but it was super busy on a Friday night especially in the summer!

    My hubby & I treated our "sudden" guests from Paraguay to deep dish pizza on Thursday (6/18). Due…read moreto all the hype I've heard and read for a couple years about Pequod's in Lincoln Park, we took them there. We still prefer Lou Malnati's, hands down. Hubby & I shared a salad... I make better salads and dressings! We ordered a large pan pizza which was overly salty with burnt crust edges. The cheese and tomato sauce were really good, but the saltiness killed it for me. The place was packed and very noisy. Not sure if it was quieter on the second floor. When you have lots of customers, it's important to have a system of checking the status of the restrooms very often. They were quite neglected. We often have out-of-town and foreign guests to host and show off our city to. We always include a deep dish pizza meal for their experience, and usually at Lou Malnati's. Always a great experience, especially the branch in downtown Naperville- consistently good. And Lou's really makes the best salad than anywhere! Sometimes for a potluck contribution I just pick up a Lou's salad, guaranteed to make everyone happy. However, our guests enjoyed the pizza and dessert; thus, I can give 3 stars for our experience at Pequod's.

    Photos
    Small deep dish with pepperoni
    Small deep dish with pepperoni
    Pequod's Pizza
    Veggie pizza

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    Veggie pizza

    The Water Hole Chicago - jazzandblues - Updated June 2026

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