Cancel

    Open app

    Search

    The Boss Bar

    2.5 (369 reviews)
    ModerateBars, American
    Open 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

    You might also consider

    Recommended Reviews - The Boss Bar

    Your trust is our priority, so businesses can't pay to alter or remove their reviews. Learn more about reviews.
    Yelp app icon
    Browse more easily on the app
    Review Feed Illustration

    Reviews With Photos

    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. 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!

    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 !!

    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
    Vanessa M.

    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!!

    Moscow mule, vodka cranberry

    See all

    4 months ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0
    Photo of Alon B.
    148
    18
    6

    4 months ago

    Helpful 1
    Thanks 0
    Love this 0
    Oh no 0

    1 year ago

    Helpful 0
    Thanks 0
    Love this 1
    Oh no 0
    Photo of Zak T.
    0
    49
    0

    6 months ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    2 years ago

    Helpful 2
    Thanks 1
    Love this 1
    Oh no 1

    1 year ago

    Helpful 1
    Thanks 0
    Love this 0
    Oh no 0

    2 years ago

    Helpful 2
    Thanks 0
    Love this 2
    Oh no 0

    6 months ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    9 months ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    1 year ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0
    Photo of Joani O.
    293
    1124
    3716

    3 years ago

    Helpful 3
    Thanks 0
    Love this 1
    Oh no 0

    1 year ago

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

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    5 years ago

    Helpful 0
    Thanks 0
    Love this 1
    Oh no 1

    4 years ago

    Helpful 11
    Thanks 0
    Love this 9
    Oh no 0

    3 years ago

    Helpful 4
    Thanks 1
    Love this 0
    Oh no 4
    Photo of Bryan W.
    56
    45
    12

    3 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    3 years ago

    Helpful 1
    Thanks 0
    Love this 1
    Oh no 1

    2 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    2 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 1
    Photo of Dan M.
    42
    119
    218

    2 years ago

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

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    5 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0
    Photo of Paul H.
    25
    77
    0

    3 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0
    Photo of Reza S.
    310
    93
    4

    4 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    3 years ago

    Helpful 1
    Thanks 0
    Love this 1
    Oh no 2

    3 years ago

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

    Helpful 1
    Thanks 0
    Love this 0
    Oh no 1

    4 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    3 years ago

    Helpful 1
    Thanks 0
    Love this 1
    Oh no 1

    3 years ago

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

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    5 years ago

    Helpful 14
    Thanks 2
    Love this 0
    Oh no 2

    7 years ago

    Helpful 2
    Thanks 0
    Love this 2
    Oh no 0

    9 years ago

    Helpful 1
    Thanks 0
    Love this 2
    Oh no 0

    7 years ago

    Helpful 7
    Thanks 0
    Love this 5
    Oh no 0

    5 years ago

    Helpful 4
    Thanks 0
    Love this 0
    Oh no 1

    5 years ago

    Helpful 2
    Thanks 0
    Love this 2
    Oh no 0

    6 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    4 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0
    Photo of A A.
    0
    10
    2

    4 years ago

    Helpful 7
    Thanks 0
    Love this 1
    Oh no 1

    2 years ago

    Helpful 2
    Thanks 0
    Love this 0
    Oh no 0

    2 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 1

    4 years ago

    Helpful 10
    Thanks 0
    Love this 0
    Oh no 1

    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

    Is there a cover charge and how much?

    No cover

    View All 4 Questions

    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

    You might also consider

    Trivoli Tavern - Corn bread

    Trivoli Tavern

    4.5(974 reviews)
    1.0 miWest Loop, Near West Side
    $$

    Had such a great night out with my daughter at Trivoli Tavern. From start to finish, everything was…read moreoutstanding. We started with the artichoke gratin and the salmon Caesar salad, and both were absolutely unreal. The flavors and quality were next level. My ribeye was cooked perfectly -- an incredible char on the outside, medium rare inside exactly as ordered, and seasoned unbelievably well. The mushroom casserole may have honestly been the best mushrooms I've ever had. My daughter's vodka rigatoni was top notch and packed with flavor. We finished with the sticky cake for dessert, which was the perfect ending to an amazing meal. On top of all that, our server Jenna was a total pro -- attentive, knowledgeable, friendly, and made the whole experience even better. One of the best dinners we've had in a long time. Can't wait to come back.

    So happy I snagged a reservation for this spot -- this was a highly rated restaurant and it…read moredefinitely lived up to the hype In regards of food: -- Pike Fish & Chips: 10/10 the reason I ordered this is because I read a review from someone who was British who said this was the best fish and chips they've ever had and I have to agree. The fish was so flaky and tender that it was falling apart. The breading was perfect. I also loved the fries it came with because they were crispy on the outside and had a good amount of potato in each bite -- Crispy Fried Chicken: 9/10 the breading was also perfect but I do think it's missing a good sauce. the dish is included with a bottle hot sauce but because I don't do spicy sauces, I did find the fried chicken a little dry on its own. Loved the coleslaw and mashed potatoes that came on the side though -- Lobster Mac and Cheese: 8/10 very creamy and cheesy but not much lobster flavor. wasn't a bad dish at all but I probably would skip this for next time because the other dishes were more of a standout -- Sticky Date Toffee: this is the dessert they're known for and I have to admit I was reluctant to try it at first. I don't really like dates or toffee and I had read a few reviews who mentioned it was a little salty. I'm not sure if they adjusted the saltiness based on feedback but I didn't find the dessert too salty at all. It felt so balanced- the warm sponge cake, the toffee sauce, the cold ice cream and crumbs for a little bit of texture all came together perfectly In the future I hope to try their vodka pasta with spicy sausage, their chicken pot pie, their cornbread, and Bella Punch or Cosmo In terms of service, our waitress was extremely attentive and sweet -- multiple wait staff were keeping our water filled and checking in with us But outside of the food and service, I will say I was a little disappointed they charge for reservations here - it's $2.50 person and even though the cost isn't that high, I think the concept of charging for a reservation versus taking a deposit or charging a no show fee is hard for me to get behind Keep in mind they also have a 3% surcharge included in the bill as well But overall I loved my experience dining here-- I think the have so many amazing dishes to try and it was so hard to choose so I definitely would love to come back to try more

    Photos
    Trivoli Tavern - Gelato & sticky date cake

    Gelato & sticky date cake

    Trivoli Tavern - Butterfinger pie

    Butterfinger pie

    Trivoli Tavern - Chicken pot pie

    See all

    Chicken pot pie

    Au Cheval

    Au Cheval

    4.4(9.5k reviews)
    0.9 miWest Loop, Near West Side
    $$

    so glad we tried this place! we actually only waited about 15 mins to get seated at the bar on a…read morewednesday night around 7pm. we came here for my boyfriends birthday and we were so happy we chose to celebrate here. the two people that helped us was antonio and issa and they made the experience 10x better. they were very attentive and friendly and just easy to talk to. gave us good recommendations and good vibes. we both really liked our drinks and were happy with the spread the food came out. we got to eat the bone marrow first which also came with this really good sauce it was almost like a meat jam but was so good on the bread and then put some of the bone marrow on for the perfect bite. now the burger, you just have to try it because it really is that good. the sauce in it was so good and it just had a really good flavor. it was just an elevated burger. we got fries as well and we shared the burger so it we were really full after. the server brought out ice cream with a candle and some sort of chocolate sauce too which just made the overall experience. we were really happy with the service and food and it just made my bfs bday that much more special and memorable.

    No good vegan options :(…read more I got the green salad and added avocado (paid extra just for 30% of an avocado) and extra dressing. Overpriced salad for sure. Also the outdoor seating was horrible. No umbrellas so we were melting under the hot sun the whole time. My friends enjoyed the fries but said the burger lacked veggies.

    Photos
    Au Cheval - The cooks were very attentive!

    The cooks were very attentive!

    Au Cheval - Crispy Fries & Potato Hash

    Crispy Fries & Potato Hash

    Au Cheval - Wings (very sticky so they come with hot towels)

    See all

    Wings (very sticky so they come with hot towels)

    Bar Siena - mini tavern burgers. april 2026.

    Bar Siena

    4.2(2.4k reviews)
    1.0 miWest Loop, Near West Side
    $$

    Last night, after a genuinely frustrating experience elsewhere, I walked into Bar Siena not…read moreexpecting much (if anything), just hoping for a reset. When I asked about the wait time, the host joked that it was two hours. Under normal circumstances, I would have laughed and played along. Given what had just happened minutes earlier, it did not quite land... but to their credit, the moment I explained the situation, everything shifted. They sat me promptly and turned what could have been a lingering bad night into a completely different experience. Julio, my server, set the tone immediately. Julio was professional, attentive, and generous. He brought out meatballs on the house, which were excellent. I ordered calamari, rigatoni alla vodka with shrimp, and what I believe was a chocolate torte for dessert (also on the house, which I was not expecting). Everything was spot on. The rigatoni in particular stood out. It was made in house and had the kind of texture and quality you notice right away. The Manager (Lance) also stopped by, having been present when I explained what had happened earlier. That kind of awareness and follow-through matters more than people realize. It what separates a place that serves food from a place that understands hospitality. By the time I was finishing dessert, I found myself watching pizzas go out to nearby tables and immediately reconsidering my menu choices for the evening. That's usually a good sign. The host who initially joked about the wait time also came by at the end of my meal. She was polite, thoughtful, and clearly intentional about making sure the experience landed well. I appreciated this gesture. When the bill came, I asked what the total would have been without the discounts and complimentary items. Once I had that number, I tipped Julio the difference. It felt like the only appropriate way to reflect the level of service and generosity I received. I'll be back (for the pizza). Overall: Food (yes) Service (yes) Ambiance (yes)

    (Kari's Rating 8/10)…read more TLDR: -Attentive Staff -Smaller portion sizes -Dark atmosphere Came here on a weekday with a friend and had a reservation for Monday at 7:30pm. We had to wait a little bit for a table so we sat at the bar because my friend and I aren't drinkers. We just had glasses of water while we waited for our table. Once we got seated, our server took our order relatively quickly and we ordered the House made for Kasha with a goat cheese and honey topping, the grilled octopus appetizer, and because we were enjoying our conversation so much we ended up just skipping Wright to dessert and ordering the gooey butter cake. For a light meal, this was relatively satisfactory. Our server said they come to the octopus because we waited so long, so it was nice that the staff was acknowledging that we waited a little bit for our table and we're willing to compensate us. As someone who lives in the river north area, I have actually been here, probably a dozen times, and it's always a good little spot but a little bit pricey for what you're getting. I would still probably come back with some friends, but I wouldn't go on my way to come here if I was bringing people off from out of town.

    Photos
    Bar Siena - Industrial bar

    Industrial bar

    Bar Siena - Parmesan Potato Skins appetizer

    Parmesan Potato Skins appetizer

    Bar Siena - This  N 24 was so delicious! I love mezcal so much  and it was the perfect birthday drink

    See all

    This N 24 was so delicious! I love mezcal so much and it was the perfect birthday drink

    HIDE+SEEK

    HIDE+SEEK

    4.0(379 reviews)
    1.0 miWest Loop, Near West Side

    The Fam and I are always looking for new places to indulge one of our favorite food groups, which…read moreis brunch with bottomless mimosas. After doing a search on Yelp, I decided we should check out HIDE+SEEK. Ding ding ding! We have a winner folks. We decided to go with the Brunch Party. First let me start off saying that Brunch Party is one plate, one side, and endless mimosas. The entire table participation is required and there is a strict 1.5 hour time limit. That said, Angelique (was our server) was on point during that time period. Our glasses never got pass the half-way mark and a good time was had by all! HIDE+SEEK has a pretty chilled vibe and the décor was cool, a very nice bar area, booths on the east side of the restaurant and tables in the front. I think there was a back area, but can't for sure as I didn't explore as we were seated immediately in our booth. Angelique was very cool. She welcomed us and asked if it was our first time there (it was) and began to explain the menu, focusing on Brunch Party and that everyone at the table had to participate, which we did. For my entrée I got the Short Rib Hash (Sunny side up egg, piquillo pepper, red wine jus, rosemary mornay) and my side was Eggs Your Way (over easy). I got an order of the Lemon Ricotta Pancakes (honey-whipped ricotta, blueberry compote, maple syrup) for the table. Both dishes were very nice. I am a sucker for anything with short rib meat in it and this hit well with me. The pancakes were good, nice and fluffy, and the compote was very good. They weren't as lemony as I have had at other restaurants. The flavor was there, but in a subtle way, almost like an afterthought, but still nice. The pancakes themselves were nice and fluffy, just they way I like them. The Doctor got the cheeseburger and fries, which looked nice. He cleaned his plate so I have to assume it was good. The Queen got the Steak and Eggs. I had a bite of the steak and it was tender and had a nice flavor to it. Overall we had a great time and while it was only an hour and a half, it seemed longer. I will totally come back here again for brunch, but want to check out their happy hour and dinner as well. The menus looks interesting.

    I would come back here, but it isn't high on my list. The food was overall good, and the menu is…read morevery creative and diverse! Even so, it wasn't enough to necessitate the price tag, which all of my friends and I were surprised by when we paid at the end. The cocktails were outstanding - we all enjoyed our choices. For some of us, they were enjoyable enough where we got the same one more than once 0:) Our server was not very friendly - she does not need to act like our BFF or anything like that, but she was cold and seemed annoyed by our questions and such. She also had no idea about the wine, so my friend just rolled the dice on what she wanted without knowing much about it. She wound up liking it - but more clarity would've been helpful (or even seeking out someone else working there for more info!). Minor environment note: The largest artwork there is a triptych of photographs - three famous women: Princess Diana, Sharon Tate (I think?), and Marilyn Monroe. There is a horizontal band going across where their eyes all line up, and the band replaces their eyes with cartoon eyes, likely of Disney princesses. It is supposed to be quirky but I found it creepy, especially since it featured three famous women who met untimely ends.

    Photos
    HIDE+SEEK
    HIDE+SEEK
    HIDE+SEEK - The Dutchess

    See all

    The Dutchess

    The Oakville Grill & Cellar - The Oakville Cinnamon Roll Exceptional!

    The Oakville Grill & Cellar

    4.1(259 reviews)
    0.9 miWest Loop, Near West Side
    $$$

    I have never written a Yelp review before today, but I had to leave my first one because of how…read morepleasant my experience was here. I came here over the weekend with my family to celebrate my graduation, and the server named Cat was AMAZING! She made me feel so special at my graduation brunch through her hospitality, witty remarks, easy-going humor, and attentiveness to her clients. If I were her manager, I would give Cat a raise because of how much she elevated the experience and excels at what she does. Additionally, the food was fantastic! The pull-apart bread was so delicious and something I would 100% come back for, as well as the short rib hash, which was flavorful and tender. The ambiance was perfect for a sunny day with a mild temperature, making it the perfect brunch spot. Once again, I cannot emphasize enough how much Cat made our time at Oakville so special. Thank you, Cat, for being so wonderful at your job and going above and beyond to make my special day even more special. 10/10 would definitely come back!!!

    I actually come to Oakville pretty often and every time it's amazing!…read more For this visit, we just did a few apps: fries, tostadas, and spinach dip. All were good but i will say that the dip was missing a little extra flavor (we added the lemon to elevate which helped). The truffle fries dipping sauce is next level & in my opinion a must try for all. The staff is always super welcoming and kind! Plus now that the patio there's not a bad choice for seating inside or out. Additionally, I attached a photo of the tuna poke bowl from a lunch visit. Easily my favorite lunch menu item they offer.

    Photos
    The Oakville Grill & Cellar - The entrance. She's GORGEOUS.

    The entrance. She's GORGEOUS.

    The Oakville Grill & Cellar - Dry Aged Steakburger

    Dry Aged Steakburger

    The Oakville Grill & Cellar - Crowded table arrangement

    See all

    Crowded table arrangement

    The Boss Bar - bars - Updated May 2026

    Loading...
    Loading...
    Loading...