City Winery Chicago

This visit was for a concert. This was the second concert attended at City Winery in the kast month. Great venue and the good selection of food and drink.

I truly enjoyed the dinner and live music evening with Robert Glasper. I’ve experienced City Winery a few times and I’ve enjoyed myself each moment. In particular, I love the wine selections and option to buy a bottle… because for us it paired well with the timing of the show. Get the truffle fries immediately! I’m a mushroom gal and the mushroom pizza was hit at our table paired with the arugula salad was chefs kiss. We sat right up front in seats A and D. We thought the sound system might be too loud but it was just right. 10/10 experience and the waitstaff was exceptionally attentive.

I really enjoyed it. Was thankful for the free street parking. And yes they sell wine🍷 🤣. Updated 03/17/2025 this was my second time coming to see a performance. This time we seen T. C Carson (Yes Kyle from In Living Single) we enjoyed the show. Be sure to download the InKind app for $50 off your $100 bill. Trust me your bill will reach that high!

What a great place for an intimate concert!! Don’t think there was a bad spot in the place! The food was decent- we ate at our venue table (very small 4 person table!) The food was good- we had the Caesar salad with chicken skewers and the kale salad with hanger steak. In my opinion, they were slightly understaffed and because of how the seating is laid out, it’s a little difficult for the staff to stand on top of everyone. Not bad service just not pinky out Service, which is fine for me. The acoustics were great. I will definitely come back for more shows. Cannot personally attest to their wine, but there was lots of it flowing so it must’ve been good. The picture was taken near the back of the venue.

Excellent venue. 10,000 Maniacs. 2/15/26

Excellent staff, didn’t get to try the food but the wine selections were great. There was a little mix up with the seating for the event but the staff was very accommodating and respectful. Definitely will return for the wine & casual dining. Great job!

I had such a wonderful time at the Boney James concert that was held on Sunday, November 16, 2025 for the 5pm show. I sat at Table 323 and I had a great view of the stage and the sound system was impeccable. The food was delicious and the public transportation was in close proximity to the venue which was a plus. I was very pleased with my overall experience.

Went to City Winery to see George Wallace 9/12/25. He was tooofunnny; and his opening comedic acts (two seasoned female comics) were funny, too. First time at City Winery. A Beautiful, welcoming, comfortable venue. Service was excellent. The cocktails were great and colorful according to feedback. HOWEVER, THE FOOD WAS HORRIBLE, HORRIBLE, and TOTALLY and EXTREMELY OVERPRICED, and SMALL PORTIONS for the expensive prices. So, be sure to eat before you go to a show at this lovely venue. Otherwise, everything else was great including the sound system. Oh…And they provide Valet Parking for $20…cheaper than a Lyft/uber; and you don’t have to worry about finding a place to park, or getting a parking ticket.

My most recent trip to City Winery was great. It was the brunch that included the Sade tribute. The singer and band was AMAZING! Anthony, one of the managers, is amazing. He’s very customer oriented and cares deeply about customers having a positive experience. We had a slight ticket issue and he helped us work it out with ease. My sisters enjoyed the buffet. My recommendation for the buffet would be to add meat items that are not fried (for those that do not eat fried foods), more non-pork and fruit options. What I didn’t know was that when there’s a brunch the regular menu is not available. So be mindful of that. Luckily, I had eaten a little bit of food before I arrived so it didn’t impact my ability to have cocktails. The cocktails were amazing! They are a bit on the pricey side, but they are delicious and worth every penny! Our server was great. I am sorry I don’t remember her name. It was a full house and she managed to keep up with everything. She checked on all of our tables and all of the guests were pleased. The atmosphere was great! It was a full house and we enjoyed ourselves from start to finish. I frequently attend events here and am consistently pleased. If you’re looking for some good entertainment, good food, good cocktails, and good service - City Winery Chicago is the place.

Great venue, NEVER have had to wait in line, room is just this side of intimate. Tables are a bit too close together but acoustics are amazing. Only minus, food is just okay but then I don't go to concerts for the food. I saw Morgan James, best singer I saw there. Ticket, Meet and Greet, dinner and a Mexican coffee just over $120.

Jeff Daniels was an absolute delight. We enjoyed the seasonal brussels sprouts salad, along with the veggie flatbread - delish! Sparkling rose cava was especially nice. Venue is cozy and we had a wonderful table who arrived as strangers and left as friends.

We had a great experience last week viewing Robert Glasper. The customer service by both Belinda and Philip was fantastic! The show was great too. Best experience there yet.

Here’s to an unforgettable night at City Winery. We visited for the first time last night and had an absolutely wonderful experience from start to finish. The vibe was immaculate—candlelit tables, champagne and wine flowing, and a beautiful live music performance setting the perfect backdrop for the evening. The staff truly elevated the experience. Manager Mikey, along with our servers Jacob and Sin, were incredibly welcoming, attentive, and knowledgeable. When we asked Mikey for the most sought-after menu items, he did not miss. The garlic shrimp skewers, hot honey flatbread, and truffle burger were all phenomenal—so good I’d honestly fight over them. We enjoyed rosé along with a flight of other wines, each one delicious and well curated. Between the atmosphere, the food, the wine, and the live music, everything came together flawlessly. We left already planning our return. An amazing experience all around—I highly recommend.

City Winery Chicago was a great experience. I went for the Chrisette Michelle concert, and the venue itself was intimate and well set up for live music. There were solid meal options available, which made it easy to enjoy dinner during the show. I had the classic wine flight and the wings, and both were good. The truffle fries were especially great—definitely a highlight. Service was decent overall. Most importantly, Chrisette Michele was absolutely amazing and put on a fantastic performance. I’d definitely return for another show.

I visited City Winery Chicago for dinner plus a show and was charmed by the intimate, wine-country meets urban vibe and exposed brick decor. The food was decent—small plates and steaks—but I thought the portions were a bit light for the price and some dishes lacked wow flavor. The acoustics and ambiance were a real highlight, making the live music feel close and immersive, though the dining layout felt cramped and tight at my table. Overall, it was a special night with good food and musical flair, but not without a few trade-offs

I recently dined at City Winery Chicago and was impressed by the quality of their dishes, particularly the hanger steak and grilled salmon, which were both flavorful and well-prepared. The ambiance was lively and upscale, with a modern industrial feel that complemented the live music performances. However, the noise level was a bit high during the concert, making conversation challenging at times. Overall, it was a delightful experience, and I look forward to returning.

Upscale venue. Very organized with getting guest seated in a timely manner pre show. Wait staff worked as a team to ensure good service. Kale salads are excellent. No seat is a bad seat for viewing. Be warned mezzanine seating may be a little snug with other patrons seated at the same table. And of course Boney James and other artists accompanying him were iconic!

Long story short, they advertised $25 tickets but I was unable to purchase it online when they were no longer available but still being offered online. I called and purchased it over the phone but they wouldn't honor the sale price, saying there's only a certain amount of sale tickets. Apologized for the developers not updating the website to reflect that. I emailed them and the responder was condescending and only refunded me $17 worth of fees begrudgingly. I was coming from Georgia and my friend Virginia, the show was great but you're required to spend at least $25 during the show. We ordered truffle fries, chicken wings and shrimp skewers. We'd finished the shrimp and truffle fries by the time they brought out the 6 chicken wings. They're small plates so don't expect to get full. That totaled $65. I love the intimate venue but it's definitely a tight space! We lucked up and there was no one else at our table. After 7 was great but even they had to adjust to the small stage, squeezing by one another. Not first time at City Winery and probably like my last but that ticket experience really turned me off!

Went to see one of my favorite artist of all time KeKe Wyatt first time at this venue and I would say that I was very impressed. What a beautiful place the vibe was everything. The employees were extremely friendly and helpful. One lady even explained the process of the wines to us, and went down a list of all the different types. The venue was very intimate, and I really enjoyed that part of it. The only drawback was food. Because this venue emails you a copy of the menu prior to you coming we already knew what we wanted to order and I was really looking forward to the kale Caesar salad. So to my surprise when I ordered it, I actually received a spinach salad, so when we told the waitress about it she wasn’t sure why it was spinach and never offered to inquire about it for us. We also order the grilled jumbo shrimp which were over cooked and we ordered the lamb meatballs, which was also very over cooked and dry. But thank goodness for the drinks. We ordered red wine and white wine and a margarita which were all very good. So City Winery you have a great place, great employees, amazing talent but not so great food😏

They do a GREAT job of booking solid entertainment But the menu choices in the venue are very limited. They removed the decent vegetarian options and most things are fried or have dairy. Either way a $25 minimum a vegetarian or dairy free diner is now challenged. They should revisit the menu and offer more meat and dairy free options for small plates Also the food coming out at different times is just chaotic.

We enjoyed the holiday brunch and Puresoul Presents: Jazz & Soul Christmas Spectacular. The show was fantastic and the venue very nice! The hosts were very pleasant & accommodating, and there was ample space for the approx. 200 guests there. Most seats seemed to have a clear view of the stage. There's a full bar and an extensive drink menu. Most of the food in the buffet was pleasing; however, there were no non-pork options for those who wanted meat. The desserts were either bland or dry/stale but the fresh fruit was tasty. All in all, the experience of the wonderful show, nice venue, pleasant wait staff, and delicious self-service coffee added to what I'll deem a great value. We'll definitely be back for more events and recommend checking out the Chicago City Winery.

Had a wonderful experience. I had brunch and the Luther tribute was very good. The singer Calen Haynes and Pure Soul put on a great performance.

I like the venue but the seats are super tight. The menu id also skimpy. The burgers are ok with a little swipe of cheese and an onion slice. I hope you like brie because that's the only option you have. There is a salad I like to get but it has no lettuce. My husband get the caesar salad and we switch lettuce for tomatoes. But I love the performance.

City Winery is a great venue for shows. It's an intimate setting to really experience an artist. It's a shame that their food service fails so badly. We recently met friends in the restaurant pre-show, and ordered an appetizer over an hour before showtime, yet they couldn't get it to the table by the time we had to take our seats. The waitress did promise to "sneak" it in to our table, yet it took another 20 minutes to get to us. We've mostly given up on ordering food there since quality is often poor, e.g. cold fries, grossly overcooked pasta, etc. If they just stepped up their food game the place would be perfect.

Went with a friend for a Motown tribute in which we purchased the add on buffet. The entertainment and live music was wonderful!! Loved the band and singers. The food was delicious. My only complaint is how tight the seating is! At our table were 4 seats, (2 on one side, 2 on the other) , too much for a small table and the next table was very close to ours , making it difficult to maneuver. (We were seated right in front of the stage). The spacing was too tight all around. However the entertainment makes me willing to return.

Great intimate venue for a show. Food is great, though on the pricey side which is to be expected. The only negative is they really pack you in with no elbow room between tables with barely enough space if you all order food and drinks. So, you’ll get to know your seat mates for better or worse. I know they are trying to maximize the space but it’s a little ridiculous. Food seemed to come out at random times which wasn’t a big deal since we ordered salads.

First time here. R&B Bingo. Very fun. Ticket price ok. I felt like the marker's (3.00 each ) should have been included , at our table alone that was a extra 30.00 for them. Food was ok , small portions and very over priced. Not a lot of food choices. They need more on the Menu. Bite size meals so don't go hungry or you will be paying a lot. The winery is beautiful and the music was great. I don't like restaurants that force you with a minimal amount that should be my choice if I want to eat or drink. The waitress sometimes hard to flagged down when you want something.

Got invited to a concert and while waiting we asked for some food… The service; (for a place that supposed to be great) was a joke, maybe the guy was new? Then ordered a charcuterie board… 🥴 Behold… the empty spaces on the board made it look like someone subtracted pieces. Also the table was wobbly, yes the table almost fall with the food and drinks. Disappointed.

Table is very small.Seating is very crammed.They try to gather to many people into one room for a show. Four people to a table, no room for food or drinks bumping Eebows and rubbing legs throughout the entire show.

I bought 2 tickets for assigned seating. Me and my guest areive a few minutes late. Our seats were taken. The staff at city winery never resolved the issue. Instead we were seated next to the stage where we could not see any of the performance. I intend to contact their Customer Relations Department.

The live music? Phenomenal. Truly heavenly. But the service? Baby… it took longer than the Rapture . I sat through the entire show like a decorative plant. Not a water, not a “you good?”, not even a crumb. Why pack a venue like a clown car and then staff it like a lemonade stand? When I finally waved someone down, he hit me with, “I’m not your server.” What un the unprofessionalism is goin on here???Sir… then who is? Casper? Because clearly my server was invisible. At that point, I just said forget it. Second, the seating situation was so tight I could hear the woman next to me inhaling, exhaling, and possibly thinking. We were basically sharing DNA. I felt like I was on Spirit Airlines….arms crossed, shoulders locked! And lastly, when the show ended, they rushed us out with the urgency of TSA in Detroit. I half expected someone to yell, “Shoes off! Laptops out the bag!” Child never again. I guess I gotta be the president to get some good service…

Overpriced for no reason! I could actually get a better seating for free near the riverwalk for free! I got 2 drinks, they were okayish, nothing to talk about. Also, they were constantly coming to check on us and wanted to see if we wanted anything else, at first it was fine but they kept on asking as if we have to order something else. We didn’t get anything else and we were halfway to finish up our drinks and they gave us the check which felt that they wanted us to leave and empty their table. We hardly sat there for half hour and left.

The greeters were very nice and bubbly, and being escorted to our seats was a nice experience. The wings, French fries, and meatballs were good but were slightly overpriced. The service was quick, but the waiters didn't know who ordered what, so they interrupted patrons who were watching the show to ask them if they ordered the food they carried by the tables. The drinks were pretty good. The seating is HORRIBLE because we were too close to each other because the tables were very small, and we felt like we were packed into a table with other strangers like sardines. I didn't like being forced to pay for food after purchasing tickets. Also, my waitress NEVER checked on us after she took our order, so I DID NOT LEAVE HER A TIP, but why did I get charged for a $18 tip for a $90 bill. My bank resolved this, but I gave CITY WINERY an opportunity to address this first, and they didn't apologize or give me an explanation. The stage and sound quality were AMAZING, but the tightly crowded seating arrangements were horrible and made us feel very uncomfortable! The DISHONEST waitress who stole an UNDESERVED TIP and the packed-like-sardines seating arrangements are the reasons why my brother and I WON'T BE EVER RETURNING TO CHICAGO CITY WINERY! Save your money and go to a local bar with good food, space, and good service! This place is OVERRATED!🙄🙄🙄

Nice space unfortunately the service was the worst I’ve had in recent memory. Went for dinner in the barrel room not for a show in the venue space so cannot speak on that. However the food was decent drink orders were wrong our server took 20 minutes just to speak to us and that was only after telling a bartender no one spoke to us. The manger came over and comped drinks but it didn’t make up for the lack of communication in the beginning. I could understand if it was busy but there were in 3-4 other tables.

We arrived early for dinner before the show. While our waitress was pleasant, there was a clear breakdown in communication. There were three of us dining, and our entrées were delivered one at a time, suggesting the order may not have been entered correctly or was misplaced until we spoke up. Other tables were also voicing complaints, and one couple even left after speaking with the manager. Overall, it was a very dissatisfying experience!

First time going here and it would have been a great experience if food/drinks were tasty and not so overpriced. My wife ordered salad and chicken on the side and chicken was smelling bad and i ordered flatbread and few pieces were too salty. I also ordered martini and it was bad (bad bartender) also had one three floyds beer and bill was about $85 before tip. I highly recommend ppl to eat and drink else where before walking into this place and spend close to $000

The host wearing the jewelry and glasses had an attitude and we didn’t know we wouldn’t get serviced if we sat at the high top. We sat down for 15 minutes and saw the nearby staff look at us and pass us over 4 xs. Meanwhile it wasn’t busy in the section we sat. The host sat us elsewhere when I inquired about seating and service. Before leading us he said “do you want a table or not?” Then we saw two other people being serviced at the table we initially picked. It still wasn’t busy. And it was the weirdest service I’ve ever had.

We set reservations for Valentine’s Day weeks before. Expressed the concern for a severe shellfish allergy, they said it would be ok at the time of the reservation( booked online and then called for allergies). Literally the night before (tonight) around 8 pm we were notified that it will be impossible to not have cross contamination for the shellfish allergy. We came into town and had this for supper (after 3 hours of searching everywhere else is booked for supper). Ruined the weekend and they really don’t care.

I’ve visited this venue a few times to see different artists, and I’ve always enjoyed the vibe. So, I decided to try the R&B bingo, but it was an absolute disaster. The ticket price wasn’t the issue; it was the seating arrangement. We were told that each person had to spend $25 and the parking was terrible. The valet service was $20 for an hour-long show. The food was also disappointing. The truffle fries were regular French fries, and the glass of wine was only half full. I paid $35 for that. The event was supposed to start at 5:15 p.m. and end at 8:30 p.m., but the next event started at 9:30 p.m. We arrived at 6 p.m. because bingo started at 6:15 with two boards of four games each, but there was no clear instruction on how to play. We were told that the host didn’t have to explain, but we didn’t understand what we were supposed to do. After three rounds, the game ended at 7 p.m. The host then walked off the stage, and that was the end of the event. It was a complete waste of time, money, and energy. The event was misleading, and I would never give this place another dime.

City Winery is one of the most corrupt and petty corporations we have encountered. My husband and I chose this venue for our wedding, as their prices, in the contract we signed, were reasonable and fair. Only after receiving ALL of our prorated deposits did they continuously, and with malicious intent, add in multiple extra fees and additional costs. After being blind-sighted by our final anticipated bill for the event, my husband and I found our original copy of our contract and noted multiple discrepancies and additional costs that were added without our knowledge or agreement. We have the receipts. By bringing this to the attention of the corporate office, we were met with aggression as they attempted to turn the tables on my husband and me for their wrongdoing. For so many weeks, I was truly crying myself to sleep thinking of how horrible this situation was, until my husband and I finally stood up to our bullies and left this amoral business. I feel awful for the people who have to work for the Senior Event Sales Director, as it is abundantly clear they operate in poor faith and without fair dealing. As a bride, I have dreamt of my wedding my whole life, and these events have tainted what should have been the best season of my life. My husband and I are good, honest people, and we are notifying the public that this organization operates out of greed and pettiness. They have no counterargument or excuse for the additional fees they added, and they have showed how unjust an organization can be once they feel they have control over you. Learn from our naive mistakes, save yourself the heartbreak, and enjoy your wedding season by avoiding City Winery.