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    The Boss Bar

    2.5 (377 reviews)
    ModerateBars, American
    Wed 3:00 pm - 4:00 am (Next day)
    Thu 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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    What started off as an embarrassing night (got stood up lol. life happens it is what it is) turned…read moreinto something memorable and a whole lot more tolerable, especially since it was my first time at this restaurant. I have to thank John and Vanessa for going above and beyond making me feel so welcomed despite what happened. Vanessa's ability to read my emotions without me saying a word and redirecting them into positivity was immaculate. John was super attentive and upbeat I couldn't even sulk if I wanted to. Those two deserve so much recognition for their hospitality and work. The food was amazing. I had the rigatoni vodka and the golden hour drink. 10/10 for both and I see why they are chosen often. Definitely recommend giving this place a try and I am most definitely coming back, whether it be by myself or with friends!

    The ambience is beautiful. It was my friend's 21st birthday. I remembered this night very vividly…read more I am still there. It is so interesting because everyone was so sweet but everyone looks like they are in school uniform uniforms from over the pond. This was a nice place and the ambience and lighting is beautifully dim and my friends look so beautiful and the match their food as well. We have tried vodka pasta from everywhere in Chicago and this one tasted uniquely like Gigi Hadid's pasta from TikTok. They were amazing with food allergies and so attentive and caring. Great staff and great service. The sticky Date cake was just absolutely heaven sent. Epic

    Photos
    Gelato & sticky date cake
    Gelato & sticky date cake
    Butterfinger pie
    Butterfinger pie
    Chicken pot pie

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    Chicken pot pie
    Au Cheval

    Au Cheval

    4.4
    (9.6k reviews)
    0.9 mi
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    Burgers were awesome. But Antonio was perfect, and went above and beyond making our dinner special…read more It was my first time in the restaurant and asked if the fries of hash was better, he recommended the fries but later surprised us with the hash comped. But that's not all-- he also came with a sunday "just to celebrate" it wasn't anyone's birthday or anniversary but we definitely were in the mood to celebrate after a night talking with him. Thanks for great service and great food, give Antonio a raise he is AWESOME

    Arrived before having to wait more than 30 minutes as others after me had to. I waited no more than…read more20 minutes for a seat. I got sat at the bar area where you can see all the action of the kitchen. The place is busy and full and I think it's awesome that it's an open kitchen cause you can see the magic happening. My waitress was super friendly and seems like she's used to everyone coming in to try the burger lol I heard her repeat the spiel many times. A single patty is 2 and a double is 3z I went with a double but honestly should have done a single. Food came out quick and the burger is super juicy. Fries were hot and delicious and even though it was the simplest burger I've ever had in my life I would say it's one of my top three favorite burgers I've ever had. Can't wait to come back.

    Photos
    The cooks were very attentive!
    The cooks were very attentive!
    Crispy Fries & Potato Hash
    Crispy Fries & Potato Hash
    Wings (very sticky so they come with hot towels)

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    Wings (very sticky so they come with hot towels)
    Bar Siena

    Bar Siena

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    (2.4k reviews)
    1.0 mi
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    We recently took a large party from work for lunch at Bar Siena. Beautiful restaurant, fantastic…read moreservice, great food. There is indoor and outdoor seating and both are elegant. Outside, vibrant with hanging flowers and tasteful covers. Inside is bright with stark woods and black accents creating a classy but casual atmosphere. We had a table of 8, and our waiter was on point, making great suggestions, was charismatic and did a great job. Every time service came, there was help to expedite the service. We ordered the calamari and meatballs for appetizers. Both were exceptional. They went quickly. I couldn't get pictures. I had the focaccia with prosciutto which was a suggestion and it was the perfect blend of savory and sweet...fantastic. Likewise, my rigatoni was exceptional. Most of the table had their signature burger and they raved about it. If you're in Chicago looking for really solid Italian food, I highly recommend Bar Sienna.

    Bar Siena is such a hidden gem! My husband and I stopped by for drinks, and it ended up being one…read moreof the highlights of our evening. The ambiance is cozy, intimate, and perfect for date night, but it's also a great place to pop in for a quick cocktail if you're out enjoying the city. Their handcrafted drinks were delicious, and I loved that they offer a full wine selection as well. We were able to grab seats at the bar with no problem, relax, and enjoy the atmosphere. If you're looking for a chic, laid-back place to connect over great drinks, I definitely recommend Bar Siena.

    Photos
    Industrial bar
    Industrial bar
    Parmesan Potato Skins appetizer
    Parmesan Potato Skins appetizer
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    Front corner
    Bandit

    Bandit

    4.0
    (672 reviews)
    1.0 mi
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    It has been forever since we dined and had drinks downtown, so when an errand brought us in the…read morearea, we couldn't leave without stopping somewhere. Decided we would hit the Fulton Market area and landed at Bandit. Was lucky to find street parking just a few storefronts away. Sat at the bar, it was not a 3-digit heat wave day and the front windows were all open, so it was confortable. Started with Jose Cuervo traditional margaritas which were refreshing. I had the chicken lettuce wraps which were really good. The lettuce was fresh and crisp, the peanut sauce had a little bit of zing and the chicken salad was very tasty. Spouse ordered the Nashville Chicken Tenders and also really enjoyed them with the scallion pancakes. 3.95% surcharge is added but states it can be removed if requested

    Bandit is a solid option if you're looking for bar food with the vibes. They had a pretty good…read moreplaylist going, and even though we visited during Taste of Randolph, they were not too busy. Our table started with the mozzarella sticks which I enjoyed, but the others didn't due to the very thin tempura batter. The entrees we felt 50/50 on. I did the chicken gyro which had a nice flavor, however felt like it was mostly pita bread and fries. For the price I would have expected a bit more filling. They also have a full bar but were unable to make a Hugo spritz which seems like a miss, especially during the summer. Overall we will return, but it isn't high on the priority list.

    Photos
    Christmas decorations
    Christmas decorations
    Chilaquiles
    Chilaquiles
    Espresso Martini

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    The Boss Bar - bars - Updated August 2026

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