The Boss Bar

Ehhhh. It’s a dive with upscale bar prices. I get this Is downtown but $14 for a SINGLE Tito’s is absolutely insane. Service was negligible. Have had way better but also had way worse. First time here. I actively sought it out tonight but unless I’m in the area I’d probably never come back simply bc $14 for a shot of Tito’s and $8 for a high noon and you have a pool table and it smells like weed. No thanks.

Make sure you bring your ID. My husband is bald and In his forties and didn't have his ID with him they would not let him in. They do have a pool table here. And mostly serve beer. They do have a full bar. I had a sex on the beach drink, it was good. For how much I paid for it I would have thought there would have been more alcohol in it though. They do have a nice outdoor area. The music is pretty loud. But they did play great songs. They filled my cocktail with more ice than the drink. I feel like I had 3 or 4 sips of my drink and it was gone. The bar is big and clean.

⭐️ 1 STAR UNBELIEVABLE EXPERIENCE 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.

Don’t buy into the fake 5 star reviews. You can easily spot them. I believe this bar shares the same security as the Taco Window next door (Same Ownership). I came for tacos late night, and left roughed up and pepper sprayed by security (Dude that has the Pringle mustache) for no reason. File a police report if you’re treated this way.

The owner will look for any reason to kick you out and hide behind the bouncers. Reading the other reviews, it seems you could just be hanging out and be kicked out. The bouncer was acting a quite weird, yelling things like "I will not yield" and "I am the vanguard". Very creepy

If you want to be ASSAULTED by a BOUNCER then this is your spot! Judging by past reviews as well it seems this is a popular trend at this establishment. Last night a bouncer assaulted a man because HIS FRIEND was "too drunk". Picked him up flung him outside, tackled him, and punched him multiple time in the face. How does that make any sense? Sounds like battery, assault, etc. to me!! Can't wait for the news to pick up this story as it seems this place is known for it.. so sickening and their bouncers need some anger management courses because they are clearly just looking to fight people.

My native Chicagoan friend took me here. The Boss has had the same owner for over over 30 years, and he was sitting right out in front of the place when we walked up at 4 in the afternoon. He even remembered my friend from back in the day! This bar is an established venue right downtown with great atmosphere and surroundings. A perfect place to have a drink or two and enjoy the company of friends.

This bar was busy. They're open late so that's a plus for people traveling late. Our food was reasonably priced. We ordered the boss sampler and two tacos. They didn't have the Long Island Iced Tea my husband ordered. He ordered a rum and coke instead and I ordered a vodka and sprite. Our drinks were over priced and watered down.

Generally, a loud bar, but if you have a problem here, it's usually you that are the problem. The people that bitch about it being racist are usually trash and too out of touch with reality. Be cool and they're cool at Boss Bar. If you want to be trash, just take it down the street to the sh*t bars.

I rarely go to bars and I rarely hangout in River North. But I'm happy to announce that I had my first pickleback shots here! And they were SO DAMN GOOD. We also ordered the mozzarella sticks and they were also incredible. The girls behind the bar were on it and were very excited to give me my first pickleback shot, which quickly turned into 3 shots. The plan was to go to Three Dots and a Dash before dinner at Roka Akor but they had a long line and was just not the vibe we were looking. Boss bar did the job and I didn't even care to read the reviews before or after coming here, that's the best. And they allow doggos.

My friends and I usually hit up Boss Bar late at night since it's open until 4 AM. It's a cocktail bar with a pool table and good draft beers. The place is in a central spot on Clark Street, which is super convenient. It does get pretty busy, so sometimes it's tough to order a drink, but it's a great spot to meet up with friends for a game of pool. The bar is huge, but the floors can get sticky late at night. If you're looking to keep the party going, I definitely recommend it!

Boss bar is our go to bar when we want to drink late in the night. The bartenders sometime take ages to take your order when it's crowded, but otherwise they are fast. I love the green tea shots that this bar offers. The ambience definitely needs an improvement. It's a bit dated in my opinion and has clearly been overlooked for a while. The floors can get really sticky too. They do offer a nice pool table that's serves as a good add on to the fun. This place is open even when most other bars are closed so it's definitely a good place to swing by when you want to keep the party going.

Busy but good. The drinks are expensive but super strong! We sat by the bar and had a fantastic time.

I was surprised and saddened to read all the negative reviews and claims of racism here. I am a Latina woman and didn't experience and issues, neither did my colleagues of color. This is right down the street from my office and we hosted a happy hour to get folks together since everyone is working different hybrid schedules now. The bouncers checked IDs at the door and it was crowded on this Thursday eve, so it was standing room only for a while. I only had a rum and Coke, but it was fine, and the music was good. Had fun socializing with work friends and would go again.

Definitely a higher class dive bar. We came in on a night of barhopping because we liked the music they were playing. Since it is a dive bar the alcohol is very minimal but do expect to pay $9 for a beer. There is 1 pool table.

if you want to find a basic white man between the ages of 23 to 35 who works in finance or consulting this is your place. Drinks are overpriced (I highly do not recommend the vodka red bull it was over $15) and music is decent, but the location is prime and the bouncers are very nice. Also, I give the bathrooms at this bar a 10/10 because they are always clean and never a long line.

Ehhhhhh, why do I keep coming back here? I used to live in town and Boss Bar was close to my office. Friends would often go there after work on Fridays. I've also spent a good chunk of a St. Patty's Day there a few years back. Recently, it was close to my hotel, so I stopped by to have a drink with a friend. The bouncers are hit or miss. Generally they are friendly but my friends were once kicked out for giving each other an enthusiastic hug when they greeted each other inside. We were shocked that hugs weren't allowed. The service is blah, they have a large bathroom downstairs, and the drinks are typical. There is a pool table in the back which is dope. Not my favorite but it's convenient.

I witnessed the bouncer from this place run to catch up to a guy that was denied entry. The guy was walking away and not turning back. He was in the crosswalk almost completely across the street. I thought it was odd because security ran past me as I was also crossing, and pepper sprayed the guy on his back. When he didn't turn around, security reached an arm around from behind him to spray his face. When I mentioned the craziness I witnessed to the staff at a nearby place (I won't say which place because they gave me the lowdown) while having drinks, they guessed BOSS Bar before I could say it, then told me that Boss does this sort of thing regularly and gets away with it because the streets are blocked for extra dining space which extends "private property" into the street. Additionally, they are protected politically as a favorite hangout of Alderman Brenden Reilly. If you have had the police ignore your reports of being attacked or robbed by the staff here call Ald. Reilly's office to thank him personally for the miscarriage of justice you've experienced. I've been here before and the food was okay, nothing to write home about. After what I saw I wouldn't feel safe going back. It's a shame because I frequent the area and feel that entire block is a danger now.

Cannot express how happy we were to find this place amidst overpriced, glamorous River North. Cheap bar, drinks are all sub $10; lots of seating both indoor and outdoor. Low price comes at a cost, obviously - the place is pretty grimy, service is fairly slow, the food is nothing to write home about (mozzarella sticks were a little gummy, fries too starchy, nothing was warm enough). But on an ad hoc weeknight in Chicago my friends and I were able to stay here for an indefinite amount of time without burning a hole in our pockets!!

The DJ and ambiance was great but the bartenders are scamming clients charging $10 for Modelo draft.

This place is off an open pedestrian street and it has plenty of seating inside and outside. Bouncer checks your ID at the door and the crowd inside is a little older. Just fries ($4) - they order all their food from a place next door, so takes a while to get the food. But pretty cheap compared to their in-house basket of fries. The dipping sauces are also good and the fries are well-seasoned. Drinks - the Moscow mule didn't taste that alcoholic but the vodka cranberry tasted pretty alcoholic. Overall, drinks were pretty small but did the job. Plastic cups. The drinks were also around $10 each, but when we ordered a second round it ended up being around $15 each? Overall, the bar is super loud and it's super hard to get your order in since the servers never come around to your table. We tried to hail some down with no avail. You have to go to a bartender yourself if you want your food or drink orders to go in. Fries were good!

Nice sports bar to enjoy the game and friends. We would definitely return. The drinks were great, I had my mules!

This place was a good vibe. We came up from California and stopped at a couple places to have a few drinks. We asked it we could smoke outside and they were ok with that as most places aren't. The drinks were great and the service from the security out front was cool! (Forgot your name man, sorry! The girl too) Thank you for the hospitality and we loved kickin it in Chi Town. We appreciate you

This bar began with such potential. The location and bouncer were superb. Then, we came during shift change and both bartenders were less than enthusiastic to be working. No specials were offered on a Friday evening. Understandable-- but upon receiving the bill, we were shocked. We ordered 2 shots, a white claw, and a PBR. The total was over 65$. This is ridiculous. 8$ for a white claw is the price of half a case. The PBR was also double the intended price. On top of the half stellar service, our shots were charged for the alcohol and for entire Red Bulls, separately. So 12$ for red bulls that were only poured into shots-- not full red bulls served. Maybe 1/4 of a redbull was used and we were charged for 2. This might be excusable for stellar service and amazing location benefits. That said, after visiting the restroom, at 6:00 pm, my first stall was broken and unable to use. My second stall resulted in sitting in an entire toilet seat of either full pee or toilet water. I left dissatisfied and frustrated. Avoid coming here if you are looking for a positive bar experience with clean bathrooms and good deals. This place over promises with prices and under delivers on every account, except the bouncers.

We are really loving this bar! Very friendly, welcoming atmosphere. The drinks are made perfectly. Perfect location in the heart of River North. And great prices. We cannot wait to take some friends here who are coming up from Florida soon!

Really like this bar, the bartenders are awesome and the service is fast. Good prices for river north.

So my friends and I were dancing! We are all black identifying. A random Mexican bus boy told us to buy a drink or leave. We aren't poor so we did. But fuck him!!!!!

If I could give it 0 stars I would. My friend was wrongfully accused of drinking alcohol from an outside alcohol and after proof they refused to apologize for wrongfully accusing him. I talked to the manager on duty and they were EXTREMELY unprofessional mindfully yelled at me (look at the camera around 11:35 by the door)

My two stars are for Ileana and her good service. If you come from somewhere with real tacos, in my case Los Angeles, i strongly suggest you stick to the alcohol. The food is TERRIBLE. I can't say this strongly enough, unless you like chewing on your shoe don't order tacos here. You would be better off with your shoe. Literally. They all said the steak was good, nachos and tortas, i have zero desire to find out. Best of luck to those that do.

Its an unsafe place to be! Be careful with the security staff they be picking random fights with people! It didn't happened to me but I have witness a lot of fights with no purpose and I have ask them why? And they don't answer back...

expensive bar but loved the vibes, surprised at the low reviews. more clubby music and young crowd. drinks were good and service was fast. the bathrooms are downstairs and had cute decor on the way which i can appreciate. would go back here for a drink!

poppin music, not much dancing, but good for watching sports! also very important: they have a pool table

The place gives racists vibes. Wearing a dress and heels on my birthday, I was told that I was not wearing the right attire, despite visibly seeing people with torn up old Jordan's and jeans (with rips) on in the bar. Very disappointed! I ended up going down the street to goose island (which I would highly recommend).

Bouncers in front are racist, degrading, rude, and disrespectful. Told us to "go back to [our] country" and to "stop doing crack" (amongst other disgusting comments) when we were reentering the bar from the street patio to use the restroom. They had a completely different attitude towards the white people we were with. It be your own people. These orders probably come from management, but these people are lost.

Place slaps! I can't have more fun at any other bar in the city! #Jenna #sistasista

Woke up this morning to a text alert from my discover card where my card was "manually" entered for a transaction that I did not do. It was done today at 4am I am in schaumburg sleep at my hotel. we were at this place on Sunday and someone has copied my card info and rang a transaction. I am PISSED. I FEEL VIOLATED. I Am traveling here to visit Chicago for the first time and this is how this establishment treats their customers. I woke up and asked my sister and brother if they had transactions on their card this morning also and my brother had 2 transactions this morning from them also. My sister is on the phone with her credit card company now to see if her card was compromised as well.. i am soo upset. So customers BEWARE!

the general manger was nothing but rude we and my friends went out to get drinks and as soon as we got there. We were told to leave but when we ask to speak to him he was hiding and trying to avoid speaking. Luckily one of friends knew the owner and that was the only way we was allowed. Never coming back.

This is a racist establishment! Me and three of my friends were getting our ID's checked when a couple of black young ladies tried to walk in. The security guard was not near the door so they thought they could just walked right in. The security guard stopped them and told them that it was reservation only... the place was super dead at that. They politely said ok and walked off. Me and my friends were immediately let in when we never made a reservation! I confronted the security guard and he said not to worry about it and that the bar is just trying to avoid fights... such discriminatory actions done by someone who is black himself. Do not support such a horrible establishment! They think they can get away with it by employing black security!

The Boss where the bar can be dead and they'll tell you they aren't allowing walk ins...great looking out for your bartenders and letting them make any money.

So... theres nothing too special about this bar but it most definitely gets the job done. When I go to Chicago, this bar is usually pretty close my hotel. Its a good place to meet my friends to catch up, in a buy a pitcher of draft beer and order a thin pizza kinda way. I have always had a positive experience with the staff here.

This bar has a great vibe and the atmosphere is just right. The pool table is great and not too expensive. I recommend this bar!

We came here after a long night and ordered a whole large sausage pizza- very ambitious of us. It was tasty, but I've had pizza from the pizza window before and remember being disappointed at how thin it was. Like paper thin- this was the case this time around as well. The amount of cheese on the pizza made up for it though. I also tried some buffalo wings, and these were tasty but small. Decent bar food late at night!

I came to Boss Bar most recently with a group of Alumni from college. We tried getting into another bar around midnight, with no success and Boss Bar had no line. The drinks are relatively inexpensive and the service is pretty quick (if you go to that bar). The atmosphere is very much fresh college graduates and young professionals under the age of 25. (I assume that crowd loves this place because it says open very late). My favorite experience was when I walked past an empty VIP booth and asked, "How can I sit there?" One of the internal security guards responded and asked if I had 8 people in my group and I responded with a resounding YES! He then wiped down the tables for us and allowed me to go get the rest of our group. Goes to show that all you have to do sometimes is ask. Thanks for the special treatment @BossBar and I look forward to coming back!

Wow! Our company had half the patrons at boss bar. On a Tuesday. And one person had Birkenstocks sandals on. The hey wouldn't let him in. I tried to understand what the no sandals policy on a very in crowded Tuesday was and I heard that the bartender got harassed by someone wearing sandals. I've clearly been to Boss Bar with many people in sandals. I'm wearing sandals in the bar where I'm writing this! And certainly will be telling all of our work teams to find a different late night work bar. Very sad as this is usually very fun.

I feel like it is hard to make me not like a bar, but this place did it. We were going from place to place checking out the food and drink scene in River North and saw this bar. We sat at the bar and saw the bartender glance over at us and then keep talking to a group of people on the other side of the bar. We stayed there chatting with them for a while before she finally came over and asked us what we want. You can tell, she definitely didn't want to me there. We ordered our drinks, just basic vodka soda drinks. She poured them and then sat on the beer cooler in front of us with her back to us. It felt very rude. We asked for our tab and she acted like we were inconveniencing her. Poor girl had to get up from her make shift chair to ring up our very expensive drinks. They were $10 each. That is ridiculous. When we left she didn't say anything to us and just sat back down. Great customer service.

Yelp tells me to select a rating - I would give Boss Bar 0 out of 5 stars, but unfortunately I have to give the establishment 1 star to post a review. I experienced not once, but twice on two separate occasions blatant acts of racism by the bouncer and manager on duty. 4 friends and I wanted to go into Boss Bar a couple weekends ago for my birthday. One of my friends who came out that night is a POC. The bouncer let my 3 friends and I in, but looks the POC up and down, and tells her "she has been over-served." A sad excuse to not let her into the bar. At that point in the night, we had all been drinking before, and that one particular friend was standing in line like the rest of us doing absolutely nothing wrong. She was not acting belligerent or out-of-line by any means, and hadn't even spoken a word while in line. If anything, I had more drinks than her at that moment, so why was I let in, and she wasn't? Absolutely pathetic. When I confronted the bouncer about the racist act, he was emotionless, and told me repeatedly "she was over-served", and "to have a good night." I asked to speak to the manager on duty about this situation, and he acted about the same. To reiterate, this was the second time I've experienced this situation over the past 4-5 years with the same particular friend at Boss Bar. It is completely unacceptable, and I will not be stepping foot at Boss Bar ever again. Not only that, but I will be telling everyone I know to never go into Boss Bar again.

I'm so glad this bar is operating during COVID times. The staff is all wearing masks and people are pretty spaced out from one another. I'm all about the vibe and I loved the vibe this bar gave off. It's like a sports bar but also super cool and has a nice anterior. The drinks weren't anything special but they were normally priced and hit the spot. The music was really good with a variety of rock, hip hop, reggaeton, and oldies. I new it would be a great bar from the outside And I was right! I'm surprised it doesn't have better reviews from others!

Employee got super aggressive when I asked if there was a kitchen connected to the restaurant and got defensive for some reason causing a bad experience. The rest of the night was staring me down and talking to our wait staff and it seemed like they were talking behind our back. Terrible experience. Have their names. But don't make it public. Boss bar-- figure it out

I've been to Boss Bar a few times. It usually has a good crowd and is always a fun time. Cheap drinks and appetizers. They are open later than other bars in the area so it is a good place to continue your evening. Service can be slow sometimes, but with the amount of people that are there it is to be expected. Overall, a good place to hang out, but don't expect anything fancy.

I wish I could leave 0 stars but I guess I'll have to give it 1 star. I understand why the bar was empty when we walked in. Out of 4 people they thought 1 one of the ID's were fake and refused to serve all of us just because the ID's were from out-of-state. The bartender called the bouncer over and I told them I could call the police to come verify the ID's then the bouncer forced us leave. This is the absolutely worst experience I've had at a bar. Only go here if you want terrible service and to be disrespected.

the first time i came was halloweekend, i was intitially denied entry until one of the bouncers asked someone and then they let me in. annoying but okay. went last night for my girls bday and we were ALL TURNT. we all had some drinks at a club then went to boss. they let all my friends in (they're white) and DENIED ME (i'm black.). They said i"looked too drunk". every time i step in this bar there's a problem only with me. other people say it gives racist vibes so i know i'm not the only one seeing this problem. y'all suck.

I had the worst experience of my life last night. During my best friend's bachelorette party- the Secuirty guard sexually harassed me, publicly shamed me, and threatened me all in one conversation. After letting my friends in, he stopped me and asked if I was from Chicago. He then told me I "can't be wearing that" and that the local bars have a "dress code" because people who "dressed like" me "make trouble and no one wants trouble." He was going to "let it slide" and when I asked what he meant or what the issue was, he kept repeating the same vague taunting statements and then said "you'll figure it out soon." I felt so incredibly violated, unsafe, and confused. I'm a 33 year old business owner and have never been someone who creates drama in bars. I ended up having to leave the party and return home because I felt so embarrassed and freaked out.

Was assaulted by the security here, punched four times and filed a police report. This place operates without any leadership and I will not return to spend a single cent. In the past 4 years I have as well with my fiancé spent thousands of dollars here. Mimi behind the bar was always a pleasant server and she made the place worth it, however the failure of this establishment to maintain a safe environment and protect its paying costumers from security personal with lack of training and discipline to deal with less than optimal situations. Enjoy the well deserved bad PR and lawsuit against your establishment.

Overtly racist and rude bouncers. I've patronized Boss Bar for the last 5 years, but after last night, I will NEVER return. In short- If you have on ripped or distressed jeans AND your skin is brown, you will be denied admittance. I visited Boss Bar at about 2am last night. I was down the street at the House of Blues beforehand and planned to indulge in more libations at Boss Bar to end my night. We walked over, hopped in line, then the bouncer informed us that they had a strict dress code prohibiting patrons from wearing ripped jeans. Both of my friends had on ripped jeans, so we couldn't enter. We walked over to talk with the bouncer, because they've both been inside with distressed jeans before. When we approached the bouncer to get further insight on the situation, he became very nasty and aggressive. We asked if we could speak with the manager, and he snarkily replied that he "was" the manager. While we were standing there, we saw not one but two white people enter with distressed jeans (one male and one female). A few moments later, an Indian girl and her boyfriend tried to enter, and he quickly turned her around for having a hole over her knee. This newfound dress code is ignorant and tasteless, but to add insult to injury, it's only enforced on people of color?! That's ridiculous. I work hard for my money, and it is green everywhere I go. I don't and won't spend my money anywhere that I'm not welcomed.

Had drinks there on Friday, had 5 mixed drinks total and the bill was 40 bucks. Went back on Saturday and we had one beer and a mixed drink and it was 25 bucks. When i asked the bartender who floated around like she was all that (NOT) about the hefty price, she copped an attitude like she was some tough ass. Piss poor attitude and of guts. Yeah u know who you are loser.

You get a dive bar feel here, FOR SURE. It doesn't quite fit in with surrounding bars as we came from Untitled a block away that had a business casual dress code. Definitely no dress code here. Our group really enjoys dive bars actually so we gave this place a shot on Saturday night. It was extremely crowded when we walked in. It actually reminded me of a college house party where people were literally shoulder to shoulder and everything smelled like beer. The music was also blasting so bye bye to conversation. We didn't have high expectations so we were in for the ride. I ordered Miller Lites for our group because there was a magical opening at the bar and I figured they didn't have many craft options. I felt really rushed ordering with how many people were trying to get each bartenders' attention. I heard someone saying that the bar went through a recent renovation and they expanded a bit. The expansion you think would give the bar a more spacious feel but it didn't. The space was still divided. Maybe it was just extra packed that night? There just wasn't many places to sit or even stand with that many people. I also heard they have some good drink deals on other nights of the week maybe to check out. They were open till 5am on Saturdays but we left well before that. All in all, if you are in a dive-bar mood, I'd check it out. I'd recommend not coming too late and avoid coming with a large group if you're planning to come later in the night.

They were really racist I came with my two black friends and they said "no urban wear" yet we had jeans like everyone else who was in that place .... Very disappointing and disrespectful I highly recommend if you are not white do not go