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    Jeffery Pub

    3.4 (14 reviews)
    ModerateGay Bars
    Closed Closed

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    2 years ago

    Helpful 1
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    8 years ago

    Helpful 7
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    Photo of Edward T.
    810
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    8 years ago

    Helpful 3
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    4 years ago

    rude, not concerned with the clientele. As we've seen the owner is clueless about the neighborhood they serve

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    4 years ago

    Helpful 0
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    Photo of Fi P.
    0
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    7 years ago

    Helpful 1
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    6 years ago

    I've been going here for years I love this place. The drinks are always good. And the staff is hilarious

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    Photo of Greg M.
    71
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    5

    7 years ago

    Helpful 2
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    6 years ago

    Great place to go out for a fun night. Drinks are awesome. Jamal Junior is a great operator.

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    Photo of Richard J.
    7
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    13 years ago

    Helpful 7
    Thanks 0
    Love this 2
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    10 years ago

    Helpful 1
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    12 years ago

    Helpful 4
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    12 years ago

    Helpful 2
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    10 years ago

    Helpful 1
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    Dick's R U Crazy - Let's play pool!

    Dick's R U Crazy

    (12 reviews)

    $

    Dick's R U Crazy is the lone successor to a Calumet region Gay scene that once boasted five (5)…read moreflourishing and active Gay bars of which one was exclusively for Lesbians. Unfortunately, Calumet City succumbed to a sad combination of white flight and city officials Hell bent on destroying the State and Stateline entertainment corridor, leveling solid historic properties into a barren surface level wasteland, that remains void to this very day. We were once guided by the bright neon signs and chasing lights, like a mini-Las Vegas strip it was. God forbid someone was drinking, carrying on, staying out until past 4 a.m. and having a Gay ole time. So here we are at Dick's R U Crazy, this lone Gay venue has been established in 1990 and serves as a beacon of life for area Gays. It offers a traditional Gay bar feel from back in the day with two (2) chalk dusty pool tables and an eclectic variety of your usual patrons. A corridor leads past the restrooms on the right that opens up into a lounge area with intimately lit tables, a stage and runway avec drag drapes. However, classic Drag shows and those once crowned as bar royalty, drag queens, have been replaced in a new world favoring karaoke. Ugh! You cannot miss what you do not know. In my opinion, today's bar music or what I heard at Dick's was a bore. It's choppy and doesn't flow one song to the next. Who wants to hear and see Seth Meyers bash Trump on Big TV screens on a Friday night in your bar? A total waste of fun time! There must be something far more entertaining and uplighting to fill in the background with to get people up and dancing. Dancing!!? What the F..k is that? One might ask! Dick's R U Crazy is a Gay oasis in a desolate desert environment that doesn't offer many better options short of going into Boystown/Chicago . Hopefully one day the Calumet Region Gay scene will rebound. Dick's R U Crazy is a continuing work in progress.

    I have never made a review before in my life, but the fact that I am now says a lot because of bad…read moreexperience they had. I went to this bar, cause I was visiting the area thinking it would be chill and fun got here at six because that's what online says but they were closed and the doors are locked. I was like OK whatever no big deal come back at 8 o'clock later but door is still locked but lights are on and This is during the winter and it's cold now I'm sitting here in the cold, waiting for my Uber to get me back home would not recommend to come here gay or not most likely they won't be open or let you in. PS this was on a Saturday night.

    The Boss Bar

    The Boss Bar

    (370 reviews)

    $$

    River North, Near North Side

    When visiting Chicago came here for a few drinks. My friend had wanted me to try a shot a of melort…read morethat he knew they had. Getting into the bar was pretty quick. Stopped Friday but didn't really hold us up much. Once we got inside, the center of the bar was fairly congested. However, the outside the bar was fairly sparse and we were able to order drinks immediately and order a second round without the issue. The bartender was friendly and the main bar when you walk in at 45 bartenders working it so people were getting served fairly quickly. While not really my scene anymore, The boss bar seemed nice enough with good service with the options to be in the crowd or have some more space if needed.

    1 STAR UNBELIEVABLE EXPERIENCE…read more LET ME BE VERY CLEAR: I have NEVER left anything less than a 5 star review before. Please check my previous Yelp reviews to see. This is the first time a place genuinely earned a 1 star. I entered The Boss Bar and said, "Hey, I'm just waiting for my Uber. It's arriving in about three minutes." IT WAS 10 DEGREES WITH A WIND CHILL OF -11. It was a Monday night and the bar was essentially empty. The security guard, who told me his name was Romero, immediately said they do not allow entry unless you are purchasing something. I explained again that I was just trying to stay warm briefly. He responded, "Why don't you go to the Starbucks next door?" That made no sense. Why leave a bar I was already inside of to wait somewhere else for a ride that was about to arrive? He kept repeating that it was "policy." I even said I was not blaming him personally, but that kicking someone out into freezing weather is a bad and irrational policy. For clarity, there were no raised voices or confrontation. Romero was calmly speaking with another security guard, and I was speaking calmly as well. Despite that, I was told to leave. Once outside on a public sidewalk, I began recording. The security guard came out threatening to call the police and said I was not allowed to film. This was not about buying a drink. It was about being treated like a problem for trying to stay warm for three minutes. NO HOSPITALITY. NO EMPATHY. NO LOGIC. I will not be back, and management should seriously reconsider how they want their staff representing this place.

    Jeffery Pub - gaybars - Updated May 2026

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