I've been to Boss Bar multiple times throughout the years and it never fails in being a casually good time. They have a huge center bar with tables around the perimeter. They have tv's to watch sports, pool tables, and good music. I've never seen it overly crowded where it was difficult to order a drink. A mix drink was about $10 which is on par for Chicago. Bartenders move drinks quick and make them well balanced. read more

The Boss Bar - Inside - Bars Near Me - Chicago, Illinois

When visiting Chicago came here for a few drinks. My friend had wanted me to try a shot a of melort that 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. read more

The Boss Bar - Bars Near Me - Chicago, Illinois

My husband was attacked by the boss bar staff after leaving the bar. 3 of them caught up to him 2 blocks away and attacked him out of nowhere. We found out that this establishment has a history of doing this and it's disgusting. read more

Anybody leaving a bad review about Boss Bar is a loser. There's always good looking girls here including the bar tenders. You never have to wait for a drink; they recently added food to the menu; there's a pool table that is the genesis of many arguments that are settled by security over who has next game. Late night the place turns into a club. Great classic pub feel that converts to a club. Next to a bunch of cool bars. Boss Bar haters- go back to catching Pokémon's with your phone and watching skin flicks with big girls in them. read more

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. read more

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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. read more

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I ordered a double Bulleit Rye on the rocks. It tasted like sweet tea. It was 6/14/26 midnight lower bar. Communicated to the bartender that this is not just a watered down shot it doesn't taste like whiskey, have any strength, and is disgusting. So the bartender made sure I was wrong and being difficult for not wanting to accept a $20 ripoff. She eventually and begrudgingly provided an unopened beer that I could assume hadn't been modified. read more

Visiting from Texas. Had a blast at this bar!! Veronica and the rest of the staff were amazing! Didn't feel any hospitality in Chicago until I came here! Definitely worth the visit!! read more

Magan is the best and it was a great bar to watch the World Cup. Drinks were good too.

Flat-out discrimination. I'm a Black male, I've been coming to Boss Bar for YEARS, and last night around 1 AM I was told they weren't letting people in. I crossed the street and watched them wave in 10 white people right behind me. When I walked back over, suddenly it was 'no ripped jeans,' so he was clearly lying and just making up a reason on the spot. There's a word for being turned away while white customers walk right in, and it isn't 'dress code.' I will never give this place my money again, and I hope they're held accountable for treating people like this. read more

Amazing ambiance and excellent bartenders who provide top notch service! Victoria provides amazing customer service and it's truthfully incredible how rapid and thorough she is with making sure that every customer is taken care of with their orders. This is an excellent Chicago spot to grab a beer and enjoy Chicago vibes. read more

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! read more

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Where do I even start... with a shot of Malort! The crew the team the staff was unbelievable. Victoria did a suburb job slinging brews. She even cut me off and helped me get an uber. I stumbled out of there with a smile on face and with a plethora of new friends. The best spot in the area with the best looking staff and crew. Be here and find out !! read more

The Boss Bar - Bars Near Me - Chicago, Illinois

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. read more

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Got scammed, came in for the 3 dollar domestics on Sunday and the bar tender served us drafts and changed us full price saying it was only for bottles. read more

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. read more

Only reason why I give this place five stars is because of the bartender amanda. I seriously love that girl so much. She is the best person ever. Her customer service is absolutely out of this world. She went above and beyond for me and my friends and made us feel so welcome and it made me love Chicago so much more (we're from CA). She made our drinks so good too!!!! YALL NEEDA GIVE THIS GIRL A RAISE AND LET HER GO HOME!!!!!!!!!!!! BEST BARTENDER EVER!!!!!!!!! I've truly never felt so happy to have her as my bartender before. Will definitely come back for her and if yall come here ASK FOR AMANDA AND TIP HER REALLLL GOOD SHE DESERVES MORE THAN THE WORLDDDDD read more

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!! read more

The Boss Bar - The boss platter - Bars Near Me - Chicago, Illinois

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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. read more

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. read more

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

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. read more

Stop by this bar when I was in town. It's a real "bar" I would recommend if your looking for an evening or after work drink read more

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. read more

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. read more

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! read more

The Boss Bar - Moscow mule, vodka cranberry - Bars Near Me - Chicago, Illinois

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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. read more

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

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! read more

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. read more

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 read more

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

The Boss Bar - a pool table with a pool ball on it - Bars Near Me - Chicago, Illinois

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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! read more

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

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! read more

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! read more

The Boss Bar - Great friends/fellow alumni last weekend at Boss Bar! - Bars Near Me - Chicago, Illinois

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! read more

I like Boss Bar when the back is open. It's a lowkey bar with drinks and food. Nothing special, but gets the job done. We paid $8 for Fireball shots, and $6 for tap beers. We also ordered the Boss Platter, chicken strips, and pepperoni thin crust pizza. It soaked up all the booze in our tummies, and made for a solid base for drinking. Average bar food and drinks. Divey vibes. Best advice: go earlier in the day to avoid boisterous crowds. read more

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

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. read more

The Boss Bar - a neon sign for a restaurant - Bars Near Me - Chicago, Illinois