I didn't eat anything here before the show, but two tablemates did. There were a ton of fries and burgers that looked good. Instead I had Diet Coke with lemon, and the server always remembered the lemon. Our server was sweet and professional. The table had a bottle of water, so I partook of water, too. I was there to see Anthony Rapp. The small theater made the show intimate and lovely! I'd definitely recommend seeing shows here. read more

City Winery Chicago - The three performing. Yes, I was close to the stage. - Wine Bars Near Me - Chicago, Illinois

The show was legit and the price was right. Valet parking is the only way to go. Now onto the venue. They cram as many people into the place as possible. 4 people at a 3' square table. We ordered a flat bread. A legit 1hr plus later it came. They comp'd it without us complaining. Knew it was unacceptable. The show is going to be good but don't expect service. Simply too many people In a too small space with not enough service. read more

So glad I'm a VIP plus member to enjoy the free valet, great concerts, wine tastings to come and more. Today's Motown brunch buffet was not to be missed. The cover band is so talented and engaging. We were dancing in our chairs throughout the set. Wait staff and Valet are very efficient and friendly. My only request for the venue is to improve their buffet by refilling the hot trays more quickly, and bringing more plates because people were waiting a bit at the prime time. read more

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Wow! What a great place and space! Went here for HH and the prices are solid! I had a hot honey flatbread and it was amazing! I had 2 cocktails, the Good Graces Rose cocktail and Nick made an awesome cocktail! I so enjoyed talking with him! My first time here but I want to return and catch a few shows! read more

City Winery Chicago - Wine Bars Near Me - Chicago, Illinois

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Go for the music it's a 5 star venue, the food is 3 stars. Nice atmosphere. Food is served "when it's ready" but I'm not sure why we had to be served our starter after our main courses? Service was so, so, a little bit amateurish. Food was ok but over priced ($31 for a small caesar salad with one skewer ((2oz)) of chicken). We had the caesar salad, tuna crunch and the short rib grilled cheese, none were memorable. The best thing we had was a bottle of Spanish Cava, which was good and realistically priced. Would we return? Yes, for the music. read more

City Winery Chicago - Chicken caesar salad - Wine Bars Near Me - Chicago, Illinois

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I went for a Saturday brunch and sat in the patio which is beautiful. I had the dip duo and that spicy feta dip is delicious! It came with crudite which is great for GF folks. I also had an egg frittata and an espresso martini. The egg frittata was low on salt and luckily I had the dip to eat it with. The skillet it came in was also so hot I burned my hand (I did get a warning from the server but still). The espresso martini also wasn't great and it had ice in it which made it watery so fast. My bf had the short rib sandwich and said it was delicious and for me the dip was my saving grace so if you're GF I wouldn't come here expecting a filling meal. Come for wine and dips and a patio vibe. read more

City Winery Chicago - Skillet burn - Wine Bars Near Me - Chicago, Illinois

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As a life-long on & off Pilsen resident, I can honestly say the food here is very good. I have dinner there every few weeks, and have brought in large family groups on a few occassional. As a Mexican Anerican, I especially enjoy mixing spicy salsas with my food. Unfortunately, whenever I ask for extra house salsa, there's none available unless I pay for additional servings (which are approximately 2 oz). This drives me crazy, as most self-respecting authentic Mexican restaurants, know their Latino customers will expect a decent serving of salsa. Especially if they're paying extra. My advice is they should simply increase their pricing, and spare us of all the nickel & diming. Very irritating. read more

A very well oiled operation. Had a great time seeing Sons of the Silent Age here. The street in front of the space is cleared for valet parking, free if you are a member. Before the show you can eat in the dining room or on the patio, weather permitting. They have a great burger and wine special some weeknights, and the burger is fantastic. There are also happy hour specials. City Winery is a negociant, and I think most of the grapes it buys are from the West Coast. The wines I tried were by and large in the new world style, although one of the reds had some old world complexity. On the whole, passable but not memorable. The show was fantastic. Sons started at 8 on the dot and played a thrilling 90 minute set. It's a great place to see an act up close and actually see them - no one stands, there isn't room! We had seats in the second row that were labeled wheelchair accessible, but they were not quite that - City Winery packs everyone in quite tightly. Fortunately two seats next to us were empty, giving us the space we needed. I would not, under any circumstances, order dinner inside the music venue, City Winery's encouragement notwithstanding. The tables are far too small. Do yourself a solid and eat in the dining room beforehand. And become a member - between the free valet and waived fees, it pays for itself after 2-3 shows. read more

Great food and friendly service. They have valet and another room where they hold shows. They offer tours on weekends of the winery. read more

City Winery Chicago - Dining room - Wine Bars Near Me - Chicago, Illinois

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Came here this week for a company event. It had snowed the week before and the entire block was iced over. Coming from Maryland, it was strange to see businesses just leave their sidewalks untreated for customers to walk on. Inside the venue itself is beautiful. The space was large and the staff was very friendly in guiding us to where we needed to be. The finger foods that were handed out were all delicious, especially the sauced chicken bites. The bread bites with ricotta cheese were my favorite. Upstairs the venue was holding a wine and cheese tasting with employees going over pairing combinations. This was a huge hit for the party. An hour or so into the dinner a caviar bar was set up which was also curated by an employee and wow, what an excellent job he did. My dinner ended up being mostly prime rib because the portions were huge and the horseradish sauce kept me going back for more. A great time was had here and I definitely look forward to eating here again. read more

City Winery Chicago - Wine Bars Near Me - Chicago, Illinois

Finallyyyy made it to City Winery after eyeing their event calendar for months! My cousin and I saw a promotion for Amber Wallin's comedy show at City Winery and we ended up buying tickets. Pro tip: unless you like front row for a specific reason, I don't think it's worth buying the more expensive seats (either way, the tables and chairs are crammed closely together). Nonetheless, we still had a positive experience! Like I said, you're sitting almost family style, right next to other guests. We had a good view of the stage and could hear clearly, even with being close to the back of the room. The servers will kind of just make their rounds and they do their best to see everyone in a timely fashion. We had to flag our girl down a few times, but as soon as we got her attention (or very shortly after) she would come to see what we needed. The drinks and food came out around 15 ish minutes after we ordered. The show was completely sold out, so I think overall, they did a great job with service for so many people. They have some upcoming shows we were interested in - Christmas drag brunch and hip hop bingo! read more

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This was my 3rd or 4th time at City Winery. The location is great. With spot hero, finding reasonable parking is no problem. I came for the Scott Evans show, which was so much fun. Scott and his guests were hilarious and entertaining. Where the night wasn't the best was the food and service. I ordered the hot honey flatbread with pepperoni and sausage. I didn't taste any hot honey so I requested a side. Aside for that the flatbread wasn't tasty. I wouldn't recommend. My sister, too, needed more sauce for her burger, and was underwhelmed with its taste. We asked our server multiple times for the sauces and he finally brought it. I believe he was overwhelmed with tables. It took him awhile to do things all evening. Our plates weren't cleared until after the show and after we asked for them to be removed. Also, during the show, a server for another table ahead of us stood blocking our view for multiple minutes. He would take an order and then stand facing the stage typing on the mobile device he had for ordering. I asked him if he could move at one point. So, the service here needs so help. But I want to be reasonable also, since I understand it's tough serving while a show is going on. I will be back for another show. I probably would eat beforehand and only order beverages next time. read more

City Winery Chicago - Flatbread - hot honey - Wine Bars Near Me - Chicago, Illinois

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This is a cool listening room. It's not a concert, as the music sets are not long. But you do get an intimate type show. There's a $25 per person minimum for a show's. If you just get a bottle of wine, then you may hit that price. The food is Ok. It's nothing special. The staff is friendly and works to get you what's needed. Overall, it's not a bad venue. read more

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Came for a social event with a large group for work. We had drinks and apps. The apps were good and my cocktail was decent in strength. The servers do a good job of checking in to see if you need more drinks and food. I have not yet had sit down service thus reserving for a follow up review in the future. read more

City Winery Chicago - Drink menu - Wine Bars Near Me - Chicago, Illinois

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I visited their concert dining section. Let me start by saying the seating area is tight. It's to the point where you can be uncomfortably close to someone you don't know. Consider that and where to sit when choosing your seats. However, that being said, it is a beautiful venue with an intimate, romantic feel. Lots of cute places to take pictures including a stand that has the business's name on it. A perfect instagram moment if you're looking for one. I ordered the Garlic Shrimp Skewers which had a great flavor and were so good. The wine, Midsummer White, was also a hit. There was a $25 food and beverage minimum for the event I attended so keep that in mind. I do wish there were more food options - but ultimately I was just there for the event. I enjoyed my visit here and would go again. read more

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Thriller performance was not what we expected at all. Cover band was ok, no dance moves, no costumes, no Zombies! It was a great show for the kids with cocktails for Mom & Dad. Happy Halloween. read more

My husband and I thought we'd get dinner in the restaurant before the Emma Nissen concert on 10/19/26. The concert was great but dinner beforehand was not. Will never get dinner there again. We got there 1.5 before the show. We were seated in the almost empty restaurant. We started with Crispy Brussels Sprouts and I asked for "no feta" (dairy allergy). They came WITH FETA. And weren't crispy. Then my husband ordered tacos and I ordered a salad with a chicken skewers. I had wanted steak but they were "out of beef". My husbands tacos were brought to the table by a random server (not our waitress) about 20 minutes later but without my salad. We waited and waited for my salad! Eventually the waitress came by and noticed I had no dinner. She went to check on it. Came back and said the chicken was on the grill it would be a few minutes. By now it's been 30 minutes since I ordered a salad. 15 minutes later it came. It was kind of a lame salad. No greens. One tiny chicken skewer. I had to eat it fast so we could get to the concert on time. No apologies or explanation from the server. No comped meal. Terrible service. PS: if you are gluten or dairy free they have very few options for us!! We will eat at Small Cheval next time we want to go to a concert here. At least Small Cheval has GF buns and good service!! read more

Went here last night for an evening with awesome chef, comedian, musician, singer, family man, all around great dude Jeff Mauro Sat front row on the stage. Had wine, appetizer, and a smash burger. Great venue with only one complaint. The seating at the tables is ridiculously tight. They seat your at a table that is built for two but they actually have 4 planned to sit there. Talk about tight , you are practically on your neighbors lap and have to eat that way. Not a great set up Smash burger was good , appetizer tray was good , and our server was good Great evening with Jeff and his family and the nice people at city winery. A must go if you've never gone. Also they have $20 valet parking or a parking garage 2 blocks west. read more

Went for a Fathers Day concert. Discovered the only food option was a trash buffet with processed eggs and Mostaccioli. MOSTACCIOLI. For $25 per person. THEY HAVE A WHOLE RESTAURANT INSIDE. But, I learned that you may not order from itduring the day. Band was excellent though! The venue is dope! The manager and the rest of it? Trash. They're going to have to extend a personal invitation for me to EVER step foot in this mf again. Ok, I'm done now. read more

City Winery Chicago - Wine Bars Near Me - Chicago, Illinois

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City Winery is a crappy venue but you can't help it going there when your favorite performers are in town. It's unhygienic (look at the photos of the dirty cutlery I was given) and the server didn't return for about 30 minutes to request a new one. The menu offers so little (options for VGF are limited) and the quantities are small. The markup on their items is insane - a cider sold at Target for $4.99 is listed for $12 + tax/tip means a $5 cider can is being served for more than $16! The acoustics in this place is surprisingly good. But most people are disrespectful of the artists and chatting away loudly (after a few forced drinks) given the $25 pp minimum F&B requirement. So you pay $35-40 for the ticket and another $35-40 (after adding tax/tip). I'd not mind that if they were at least forcing you to enjoy something enjoyable - they have lowered the bar so much knowing it's all mandatory anyways. read more

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Y'all...table flip! Riot in the streets! City Winery got rid of all the good stuff on the menu! Kung pao cauliflower? Kung fu off the menu! Potatas Bravas? Adiós! Even the wedge salad has been shoved off the page. Super sad. I've ordered those things every time I've been here, except today. Instilling a $25 food/beverage minimum AND hatcheting your menu. BOOOOO. Boo on you, sir! Caesar salad $19 what the actual fork? And it doesn't have croutons. But my companion who ate it said it was still delicious and the lettuce somehow overcame the lack of crouton. Alright so what DO they have going for them? Well Alex in the dining room did a fantastic job choosing the perfect mocktail for me, the non-alcoholic sangria. It's delightful! I had three of these suckers. The staff is swift and helpful. Matthew was very well versed in the menu, despite some of it going over my head. He works it! Honestly Alex and Matt pull a 2 star review into 4 star territory at least. If I MUST be disappointed by idiotic changes to menu and policy, at least the staff is still excellent. You go Alex. You go Matt. Werrrk! So what do they offer that can possibly compare to my old faves? I tell you - the Greek Sliders are where it's at. They're a decent portion, though my compulsion would say skip everything else and order two of these because the kafta meat is phenomenally seasoned, tender, mouthwatering...and the feta and pickled onions take it to a whole nother level. The real star of the show, though, is of course the sound quality and caliber of show you get. There's just no other venue quite like this. You get to sit down and watch the artists on stage with excellent quality and a level of intimacy you don't get at other music venues. It really is a venue for an older crowd because you don't have to wait your way through opening bands, the show starts on time and ends at a decent hour instead of late into the wee hours. You can have dinner and a show and still get home to sleep without feeling completely exhausted. And even for younger folks, it's a great spot to catch an early show before partying the rest of your night elsewhere. I'll keep coming back if an artist I really love is playing here. And I'll order the Greek Sliders and the NA Sangria. So please don't take those off the menu City Winery! read more

Bridal shower the loft-Service and the food were spectacular. Only concern we had was no communication from the catering manager, except through my email. The space is not enclosed totally so a little noisy with the gospel brunch downstairs. Also, they only allow you 30 minutes to set up before an event. That was not enough time. read more

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Came for the Music Soulchild show and had a lovely date night! Had a couple drinks and food with the show which I think is a lovely way to enjoy an intimate concert. The place is set up well where you can see the stage no matter how far because it's not a huge space. The server comes and checks on you periodically but there's also bars you can go to inside. read more

City Winery Chicago - Wine Bars Near Me - Chicago, Illinois

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Last two visits my friend never got their order at all though I got mines hard to understand how this could happen twice in a row...

I went to a comedy show here and the experience was just okay. We had front row table seats, but the setup was way too cramped. The table next to us was less than three inches away and the table was up against the stage. So we had to move just to sit comfortably, which was disappointing since we paid for front row. Otherwise, my guest and I would have been sitting shoulder to shoulder, leg to leg, and would have been bumping against each other to eat or drink anything. The venue wasn't that packed, so I don't understand The seating arrangement. I had pre-ordered a bottle of wine and we realized it was full of gnats after it was served to us. The manager handled it well and replaced the bottle at no charge. It would have been nice if the server had acknowledged this happened and offered any apologies or allowed us to order something else. But she never came back after she realized we were getting another bottle and the manager came over. She only acknowledged it when it was time to wrap up payment. The food was excellent, a little pricey but worth it. I'd definitely come back for the food and the show, if it's someone that I really want to see. I hope the seating and wine service improve next time and this was just a one-off event. Overall, considering the parking situation, the seating experience, and the way that the wine issue was handled, I would not go out of my way to visit this venue again. read more

Went to City Winery for a John Gorka concert and really enjoyed it. The space is beautiful, exposed chicago brick everywhere, big archways, tasteful and fun decor. The concert seating is really nice, just tables and chairs around the room with some nice dim lighting for the show. The staff was helpful as well. We got the charcuterie board with some beef sliders and some wine. Everything was good! It was a teensy bit pricey but really not bad for the west loop area. Big fan of the zinfandel wine they served, and of course it went well with all the food we got. I would definitely come back here for a concert! The vibe is really relaxed, it's great to be able to enjoy some food with the music. Overall great time. read more

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Excellent Pinot Noir, great outdoor seating, and friendly service. The flatbread pizza was fresh and hot. Will be returning soon!

I really like the shows at City Winery because they are small, often new and upcoming artists. The food is just okay and definitely overpriced, but because the whole point of the visit is the show, I do let that slide. I love the complimentary wine that you get when you come in. The servers and staff are always very nice. The venue is well kept, always clean, beautiful decor. The only thing I do not like about City Winery is the seating. It is way too cramped and it affects the customer's experience. If there is someone that I'm on the fence about seeing, I will choose not to see them because of the seating situation. I only endure it when it's someone I really want to see. read more

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My husband and I spent my August 1 Birthday weekend T the City Winery in the West Loop. Friday night for the Eric Roberson concert. Amazing. Eric Roberson was excellent! Excellent repertoire; warm and interactive performance. Our waiter Brandon was attentive and made excellent menu recommendations. We had the prime rib grilled cheese and the lobster ravioli for dinner. Both were good. Their wine selections are definitely better than their cocktails which were weak and not flavorful-,even with Don Julio tequila. On Saturday. We booked the wine tasting. Destiny was amazing!!! Informative and personable. Shared the technical information about each wine with a personable and reflective observation. She made the experience memorable and accessible. We have for many wine tastings in Traverse City, Lake Michigan, Niagara NY and Sonoma valley in California; Destiny was by far the most indeed and impactful experience we have had . She is truly gifted with the ability to share head knowledge and heartfelt love for the adventure and experiential aspect of wines. Destiny has made us sure that we will be coming back to City Winery with our friends and family from Michigan. We look forward to making City Winery one of our "frequent fliers" for music and wine. The food was okay not stellar. Doesn't matter; we'll be there for the music and the wine experience. I hope you have the opportunity to have Destiny for your wine exposure experience. She's a treasure. I hope they harness her enthusiasm and wine enjoyment for future guests. It was a remarkable and truly memorable weekend with City Winery! read more

City Winery is a fully functioning winery with incredible live music, so you're sipping house-made wine while catching amazing artists up close. It's one of those venues where the vibe, the food & the music all come together perfectly! read more

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Went here for a comedy show. I really enjoyed my food and drink. I shared the truffle fries with my friend. It's a big portion size. The fries are the shoelace fries for fry lovers (lol). I also ordered the lamb burger sliders. They were cooked perfectly and tasted great. I even ended up reheating one the following day and it still tasted as good as when I ordered. The ambiance is dim lit and vibey. Our server was knowledgeable about the menu and very attentive. I recommend this location for events or just a good time. read more

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City Winery offers some great events, but unfortunately, the seating arrangement leaves much to be desired. The space is so cramped that it's difficult to move around, and sitting so close to people you don't know can make for an uncomfortable experience. We attended a Michael Jackson tribute brunch, which had some nice elements but also some notable issues. While the brunch itself was enjoyable, the setup was less than ideal. There was barely any room for multiple plates at the table, and I was shocked that the hot food wasn't kept on burners--resulting in extremely cold eggs. Speaking of cold, there was also cold air blowing directly onto our table, so a few of us ended up wearing our coats throughout the show. On the plus side, the staff was very friendly, which helped improve the experience somewhat. City Winery has potential, but I hope they reconsider their seating arrangements and food service setup to make the experience more comfortable for guests. read more

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City Winery is my go to for a fun evening of wine or entertainment. Now that I have a wine membership I make sure I come for the pickup parties. The food menu is ok. They have happy hour specials from 4-6pm Mon-Fri. They also accept the inkind app payments. Valet is $20 but if you have the wine club membership you get complimentary valet parking. I here for the wine. read more

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Was very excited to try this place, and had high hopes, but was very disappointed. The service was terrible. We weren't greeted when we walked in, and had to wait 20 minutes after our reservation because our table "wasn'rlt ready". The service was also bad. I never did get my soda refill that I asked for twice. I am not one to write bad reviews usually, but for the price, I thought it was a big let down. read more

The show was great. The tables are packed shoulder to shoulder.! People are allowed to block your view by holding up their phones Waiters are tripping over you to deliver food. The entry line was super slow. The show started 30 min. late! Unforgivable! Earth, Wind, and Fire Tribute Show! read more

Average food and average collection of wine. Their setup at the river walk is definitely good for the views only.

Not much room and that little bit reduced the overall comfort. I ordered the City Winery Sangría -- while the drink had more ice than beverage, it still tasted good. But the food was poor. The staff seemed a little disheveled, with several orders being delivered to us in the wrong order, although that night it was a full house. Nevertheless, they were highly courteous and dealt with the problems in a professional manner. read more

*VENUE SEATING REVIEW* Visited City Winery on Tuesday for Pink Elephant tour "Mara Love" and we were packed in like sardines. I purchased premier ticket but probably would have been more comfortable in rear. ABSOLUTELY TOO CLOSE FOR COMFORT!! I couldn't enjoy the dinner, drinks and show for continuously apologizing for rubbing arms with the person next to me. The chairs are SO close you have to try and pull the chair all the way out, sit then scoot up. Not even room to place hands on sides without rubbing the person next to you. Barely room to place food and drinks on table( that you are required to purchase). I had to sit with shoulders up and arms crossed in front of me. Beyond intimate. Please consider if you're afraid of Covid. read more

Canceled Raheem DeVaughn Show (Dec 29) 2025 Dear City Winery Team, I am writing with genuine heartbreak over the abrupt cancellation of Raheem DeVaughn's December 29th, 9:30 PM show. I purchased my ticket the day his return was announced months ago in 2025, and I was notified of the cancellation on extremely short notice, with no meaningful explanation. (Like a few days before the performance) This show was not just a night out for me. It was something I had been looking forward to for months--a moment I carved out of my life and budget intentionally. I paid for flights, hotel accommodations, a rental car, travel expenses,not to mention my outfit makeup and hair !!! None of this is refundable. I absorbed those losses quietly, but the disappointment has been heavy. I have supported City Winery faithfully for years. I have attended every Raheem DeVaughn headline show at your venue, always seated in 230A. I have overlooked discomfort, pricing, parking issues, and service concerns because the music mattered to me. Even after past cancellations and serious incidents at the venue, I continued to show up and support you. What hurts most is not just the cancellation--it's how little care was shown afterward. A brief apology does not acknowledge the time, money, and emotional investment this moment represented for me. I have not been offered compensation, consideration, or reassurance that my loyalty is valued. In a difficult economy, experiences like this are not small things. This was my highlight. It was taken away, and I was left carrying the loss alone. I am asking, sincerely, how City Winery plans to acknowledge and compensate patrons like myself who were affected by this cancellation. I want to continue supporting your venue, but I need to feel seen and respected as a human being--not just a ticket number. Thank you for taking the time to read this. I hope you will respond with care. Sincerely, Qiana langston a Real dedicated supporter read more

City Winery Chicago - Wine Bars Near Me - Chicago, Illinois

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Drinks and apps - their appetizers were HUGE. Everything was delicious and service was quick. Couldn't recommend more if you're going to United Center afterwards :) read more

City Winery Chicago - Pinot noir - Wine Bars Near Me - Chicago, Illinois