City Winery Chicago

Reviews

• CO

  Crush Onastick

  4 days ago
  2.0
  This was my second show at City Winery in Chicago and it will be my last. Our table arrived at doors at 5:30 and the server did not come to our table until 45 minutes later. This was the same experience we had the first time went—waiting more than half an hour for someone to take our order and never having an opportunity to order a second drink. The food was mediocre, not up to midrange Chicago restaurants at all. For $140 for two people (on top of the show ticket), I'd pick anywhere else over City Winery. The performers were fine, but the arrangements of the tables and chairs has the stage to the side of the audience. You have to twist sideways in your chair to see anything (there's not room to turn the chairs themselves sideways). After a terrible first experience, I figured I'd give the place a second chance, but it was just as bad the second time around.
• IL

  Isabella Santiago Lindsay

  Jul 3, 2026
  1.0
  I went to city winery for happy hour today. The website says M-F 4-7 PM. I was with myself and one other person. we came in explicitly stating that we would like happy hour. Our waitress said OK great this part of the menu is happy hour. This part is not, then we ordered. Then she came to us with the Bill saying oh this actually isn’t happy hour “you never said you wanted happy hour”. Then we go to talk to the ladies at the front and they said let me talk to our manager to get your price adjust adjusted for happy hour prices. Then she comes back to us and says actually today is not happy hour. Please avoid this place at all costs. we are very disappointed in the service and lack of understanding by the entire staff that we dealt with. If you say something is happy hour and go into detail explaining the menu, do not LIE to us to say you never said that. I come from a food service background, and I have a lot of empathy for people who are new or learning their restaurant, but this would’ve never happened under my watch. Truly horrible customer service.
• VB

  Vee Black

  Jul 1, 2026
  5.0
  Absolutely love visiting The City Winery. Whether it's for a show inside. Or sitting outside in the summer. Drinks are always A+ Food always delicious 🤤😋 Staff Always friendly and polite!! The tables are set beautifully. 10/10 for atmosphere, location, food, drinks and Staff!!
• AB

  A B

  Jun 30, 2026
  3.0
  Pro: This was my very first time there on Saturday June 27th. We we're there to see "Tee Sanders" the comedian. The show itself was really good and well put together! This was my first comedian show and won't be my last. Cons: There were too many chairs (12) at the tables. Made it a little uncomfortable. Luckily a few people didn't show up to the left of us. Or it would've really been super uncomfortable. Hardly no room to eat. They need to heavily reconsider maybe taking it down to 8 chairs per table. But I get it? Trying to pack them in there like sardines to get a good crowd each concert or show. The Chicken Bacon flatbread that I got wasn't that great at all. I thought it was very ballsy of our serve (who left us hanging most of the night) to ask me to "give" her a nice tip! Smh! I always tip when it's good service. But to implie she needed a "nice" tip was very off putting. Unsure if I would return because of that very "comment" she made too me.
• SC

  Stephanie C

  Jun 29, 2026
  5.0
  I went to City Winery for the first time to see SeJoe and honestly, I didn’t expect the part I’d remember most would be the people. I’ve been so busy with school that I really haven’t had the chance to go out or even celebrate my birthday, so this was a big deal for me. The venue was great, the seats were better than I expected, and it was just nice being outside surrounded by good comedy. But Belinda is what made this night unforgettable. When she found out we were celebrating my birthday, she made me feel so incredibly special. I can’t fully explain it, but some people just have a light about them and she’s one of those people. She was so kind and genuine and her son was also so attentive to us as well. They both made me feel truly cared for and made the whole experience that much more special. Their kindness meant more than they’ll probably ever know. I wish more companies understood how important it is to hire people who genuinely love being around others and making people feel welcome.