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    The Boss Bar

    2.5 (377 reviews)
    ModerateBars, American
    Closed 3:00 pm - 4:00 am (Next day)
    Updated over 3 months ago

    The Boss Bar Photos

    Business Info

    THE BOSS BAR ATMOSPHERE

    What's the vibe?
    Moderate noise
    Juke Box
    Happy hour specials
    Good for groups

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    Recommended Reviews - The Boss Bar

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    Inside
    Miranda L.

    I've been to Boss Bar multiple times throughout the years and it never fails in being a casually good time. [[HIGHLIGHT]]They have a huge center bar with tables around the perimeter.[[ENDHIGHLIGHT]] [[HIGHLIGHT]]They have tv's to watch sports, pool tables, and good music.[[ENDHIGHLIGHT]] 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.

    Mike P.

    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. [[HIGHLIGHT]]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.[[ENDHIGHLIGHT]] The bartender was friendly and the main bar when you walk in at 45 bartenders working it so people were getting served fairly quickly. [[HIGHLIGHT]]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.[[ENDHIGHLIGHT]]

    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.

    Paulina A.

    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. [[HIGHLIGHT]]Boss bar did the job and I didn't even care to read the reviews before or after coming here, that's the best.[[ENDHIGHLIGHT]] [[HIGHLIGHT]]And they allow doggos.[[ENDHIGHLIGHT]]

    Nikhita T.

    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. [[HIGHLIGHT]]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.[[ENDHIGHLIGHT]] [[HIGHLIGHT]]The bar is huge, but the floors can get sticky late at night.[[ENDHIGHLIGHT]] If you're looking to keep the party going, I definitely recommend it!

    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. [[HIGHLIGHT]]I stumbled out of there with a smile on face and with a plethora of new friends.[[ENDHIGHLIGHT]] [[HIGHLIGHT]]The best spot in the area with the best looking staff and crew.[[ENDHIGHLIGHT]] Be here and find out !!

    Mayuri A.

    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.

    The boss platter

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    Review Insights

    2 months ago

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    2 months ago

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

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    2 months ago

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    2 years ago

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

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    3 years ago

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

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    3 years ago

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

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    4 years ago

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    5 years ago

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    3 years ago

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    3 years ago

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

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    9 years ago

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    Page 1 of 10

    The Boss Bar Reviews in Other Languages

    Ask the Community - The Boss Bar

    Is there a lost and found? How do I get in contact?

    Is the Tuesday Burger and Beer for $10 worth it? Thanks!

    Absolutely

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    No cover

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    Review Highlights - The Boss Bar

    It's divey, it doesn't have much going on besides a jukebox and some drunks, but I always have a great time.

    Mentioned in 11 reviews

    Read more highlights

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    Three Dots and A Dash

    Three Dots and A Dash

    4.1
    (4.2k reviews)
    0.0 mi
    $$$

    I made reservations at Three Dots and a Dash to kick off my sister's bachelorette party. She loves…read moretiki bars, so it was only appropriate to gather and welcome everyone. OpenTable only allowed up to 8 people per reservation at a time. We were a party of 13, so I had to split the reservations into two. I made a request for the tables to be close together, but I understood that there was no guarantee the tables could be together. Our reservations were at 9pm, and the place was packed. Three Dots and a Dash did us a solid and managed to reserve an entire alcove for us! I was so appreciative. Loved the vibe at Three Dots and a Dash. It felt much classier, like a mid-century modern tiki lounge. The music was fun too. Instantly recognized a retro Italian song by Pino D'Anglo, which just added to the ambiance. The drinks were great. We ordered a couple of rounds of the shotstapus, and I got the rum barrel for good measure. The drinks were sweet but tasty. Too easy to knock back.

    When I was visiting my friends in Chicago, they insisted on bringing me to Three Dots and a Dash…read more We were able to walk-in on a Friday evening, although we were relegated to standing room only since we weren't able to get a reservation. Upon entering the bar, I felt like I was entering a catacomb with skulls lining the entrance. The bar was packed, and we squeezed in at the bar to order our drinks. The drinks were on the pricey side, but I appreciate how the cocktails are garnished with real fruit (mine had lychee and dragonfruit) and was served in a fun tiki glass that was unique to each drink. The setting is a huge part of the experience, and I had a fun, memorable evening.

    Photos
    Interior Entrance
    Interior Entrance
    These Loaded Luau Cheese Fries
    These Loaded Luau Cheese Fries
    Tiki gift shop.

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    Tiki gift shop.
    Ghost Donkey

    Ghost Donkey

    4.0
    (69 reviews)
    0.1 mi
    $$

    We originally came to Ghost Donkey as paranormal investigators, after being hired to locate the…read moremissing ghost donkey belonging to a local agave farmer. The case had gone cold--or perhaps mezcal-hot--until we received a clue pointing us toward River North. Ghost Donkey is spacious, colorful, and full of energy, with plenty of bar seating and tables. The music can get loud, but it fits the atmosphere perfectly. The bartenders were constantly interacting with guests, swinging the lights, encouraging the crowd, and turning the entire room into a neon-lit fiesta. They do have a food menu featuring items such as tacos, nachos, quesadillas, and guacamole, but we mostly came for the drinks. Many of the cocktails are tequila- or mezcal-based, which is exactly what we enjoy. The menu is creative, the drinks are strong, and the bar does an excellent job making agave spirits approachable--even for guests who may not consider themselves mezcal experts. After two drinks and an argument with a decorative donkey, we finally found the missing spirit hiding behind the bar. He was translucent, smelled faintly of roasted agave, and appeared to be carrying a tiny map. We followed him through a glowing hallway, down a staircase, and into a secret chamber where he revealed the legendary piñata of Quetzalcoatl, the ancient feathered serpent god. Naturally, we attempted to break it open. Instead of candy, it released a cloud of mystical dust, three lime wedges, and a receipt for nachos. The ghost donkey brayed with laughter, the lights began swinging, and the entire bar erupted in applause. The bartender handed us another drink and told us this happened all the time. Ghost Donkey is a fantastic place to hang out, pregame, and enjoy inventive tequila and mezcal cocktails in a lively setting. Just be warned: you may arrive looking for a ghost donkey and leave having helped recover an ancient Mexican god's piñata. That's simply the sort of evening this place encourages.

    The three stars are for the HH, vibes, and chicken tinga tacos. Other than that, I don't really get…read morethe hype and I've been here several times. The happy hour prices are decent, but I just really don't like the drinks. I feel like the options are limited and just not that good tbh. Reservations are encouraged, but you can also chill at the bar if there's room. This is a spot I'd go to after the main event, not one that I'd specifically leave my house for. Everyone else in my group always seems to enjoy, so maybe it's just me!

    Photos
    Ghost Donkey
    Ghost Donkey
    Ghost Donkey

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    Rossi's Liquors

    Rossi's Liquors

    4.2
    (433 reviews)
    0.2 mi
    $

    Friendly and lively dive bar (4/5 Green Stars) Waiting for…read moretake-out from nearby Lou Malnati's, we wandered into Rossi's for a quick drink. It's a reasonably-priced busy dive bar in the heart of Chicago. I asked the bartender if she had a beer + shot deal and she said "no, but you can order a beer and shot." And so we did! Noise level is fairly high, thanks to a lively crowd plus a jukebox. They don't normally serve food but I think are fine with customers bringing in your own food, and you can also place an order from a nearby restaurant (I don't recall which one). And yes, it's cash only so bring some money if you don't want to pay ATM fees! 4 out of 5 Green Stars for social and environmental impact. I like bars that allow customers to bring (or order) their own food - it allows for all diets! The one thing I'd like to see is more beer on tap - even just one good rotating local beer (e.g., Goose Island). Draft beer has smaller environmental footprints compared to bottled or canned.

    Recently stopped by Rossi's Liquors and this place is the definition of a dive bar, in the most…read moreauthentic way possible. After a quick ID check at the door, the bouncer let us know it's cash only (thankfully we came prepared). From the moment we walked in, dim lighting, loud music, and shoulder-to-shoulder crowds gave the vibe of a full-on frat party, but not in a bad way. It's chaotic, energetic, and unapologetically no-frills. There's even a self-serve cooler with drink prices clearly listed underneath. I grabbed a Sapporo Premium, brought it to the counter, and our friendly bartender broke our change and offered a chilled glass to pour it into. Simple and efficient. That said, it was loud, so loud that even whispering-distance conversations were a struggle. The space is small, seating is limited, and since we couldn't snag a spot, we ended up leaving shortly after finishing our drinks. This feels like a better weekday hang than a packed weekend night. Still, if you're looking for a classic, gritty, no-frills dive experience, Rossi's delivers exactly that.

    Photos
    Nightcap
    Nightcap
    Rossi's Liquors
    Rossi's Liquors

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    Gus' Sip & Dip

    Gus' Sip & Dip

    4.5
    (176 reviews)
    0.1 mi
    $$

    We were seated quickly, attended to quickly, and it has a great ambiance - it almost feels like a…read morespeakeasy. We got two appetizers, and were extremely impressed by both - they came within 5 minutes. We each ordered a cocktail and they were fantastic as well. We will 100% be coming back.

    This might've been one of the best experiences my friends had on their trip to Chicago. We came…read morehere on a whim based off of convenience. My friend got really hangry at a certain moment while we were walking so we came here since it was open, had great reviews, and appeared to have a happy hour going on. We had to wait a little more than 5 minutes outside for a table, but the host was nice and got us accommodated. We were surprised by the inside and the amount of people dining in. From the outside it looks very basic and nothing too fancy. Our server was great and took care of us well the entire time. We ordered some Long Islands because they had a $6 happy hour up until 5pm and I have to say it's probably one of the best long islands I've ever had. All of my friends agreed as well. We were doing some appetizers so we got their style of cheese curds order, some crab rangoons, and pretzel with sauce/cheese to share. Those cheese curds were insanely good. Everyone at our table LOVED them. We wouldn't stop talking about them and had wished there were more. The ranch was excellent as well. We didn't like their marinara though - a bit too watered down. These curds were shaped more like cubes which isn't the traditional way they look, but unique and SO delicious. We also really liked the crab rangoon here. Pretzel was ok, but nothing crazy. They cheese that came with it was excellent though.

    Photos
    Pinky Gonzales
    Pinky Gonzales
    Gus' The Original Wagyu Beef Dip
    Gus' The Original Wagyu Beef Dip
    Gus' Proper Burger

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    Gus' Proper Burger
    Ila's

    Ila's

    4.8
    (70 reviews)
    0.1 mi

    Ila's is a lovely, hospitable restaurant with delicious food. it was a great experience and I will…read morereturn.

    When I was planning my sister's bachelorette party, I wanted to find a restaurant near our hotel…read morethat could accommodate different dietary preferences (i.e. no pork, vegetarian/halal, etc.). I found Ila's on Google and liked the variety of menu items. The food appeared to elevate comfort food from multiple cuisines, such as American, Italian, South American, Asian, and Southeast Asian. I reached out to the restaurant and was assisted with a reservation for 14 people. Our table was set and ready to go as soon as we arrived at 8:30pm on a Saturday. Overall customer was excellent. Thank you to the hostess for making my sister, the bride, feel special. She complimented her and hyped her up for the night, which was really sweet. Our server was awesome too. He was friendly and highly attentive. Loved that our food and drinks also came out in a timely manner. I enjoyed everything I ate. I had a few bites of the appetizers including the scallops, fried paneer, and 2 kinds of empanadas (corn and chicken). We also got lumpia and a mixed bread platter for the table. Though I didn't have any of the latter, they were a hit at our table. I got the burger as my entree, and it was such a redemption from a crappy burger I got elsewhere earlier in my trip. The double smashed patties were juicy and flavorful. I devoured the burger and loved the thin cut fries. All-in-all, we had a lovely dinner at Ila's for my sister's bachelorette party.

    Photos
    Nico collin's & hugo spritz
    Nico collin's & hugo spritz
    Assorted Savory Kabobs: Paneer, Chicken & Leek, Pork Belly
    Assorted Savory Kabobs: Paneer, Chicken & Leek, Pork Belly
    Happy hour $10 sparking rose. fantastic!

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    Happy hour $10 sparking rose. fantastic!
    O'Callaghan's

    O'Callaghan's

    3.5
    (317 reviews)
    0.1 mi
    $$

    First the atmosphere and service were amazing! Friendly and helpful when needed but not overly…read morepushy' I got the mozz sticks and they were on point. But let me tell you about the grilled cheese! This is no normal grilled cheese. This may have been the best grilled cheese other than the ones my grandma made me as a kid. I chose pepper jack cheese with bacon. The sandwich came out on Texas toast with the perfect amount of crisp on the toast. The sandwich has the best cheese pull and the bacon was perfectly crispy. The waffle fries well I couldn't even finished because I devoured the sandwich so fast. Highly recommend this place for anyone looking for a friendly dive, cold beer, solid bar food, or wonderful grilled cheese!

    I came in with three friends and we grabbed a high-top table. We ordered a few rounds and…read moreeverything was going fine. Toward the end of the night, two of my friends left, and the remaining two of us paid our bill and were finishing our drinks while waiting for our Uber. At that point, the bartender came over and told us she needed our table for a large group. The table wasn't reserved, and we were clearly just finishing up. We told her we were about to leave anyway, but the way it was handled felt really abrupt and rude. What made it worse was that she immediately brought a group over to take our table, and even they were apologizing to us because they seemed uncomfortable with how it was handled. I've worked in bars and restaurants myself, so I completely understand needing to manage space, but there's a way to do it respectfully, and this wasn't it. Unfortunately, this experience left a bad impression, and despite having been here multiple times before, I won't be returning.

    Photos
    Dining Room
    Dining Room
    Smokehouse Burger with tots
    Smokehouse Burger with tots
    O'Callaghan's

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    The Boss Bar - bars - Updated August 2026

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