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    Webster’s Wine Bar

    4.1 (147 reviews)
    ModerateWine Bars
    Closed 5:00 pm - 11:00 PM

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    a glass of red wine
    Kyle P.

    Despite having such a bustling culinary scene that now includes some incredible places to enjoy craft beer and spirits, Chicago is not necessarily know. as a city in which to enjoy great wine. Webster's changes that narrative, showcasing some great glass pours and bottles along with a nice food menu and a truly relaxed vibe. It's all about service, creating an experience. Our bartender was kind and friendly, happy to answer any questions, engage us for a brief conversation, and also when to just kind of leave us to our own conversation. You truly can't go wrong with the wine choices, there's something for everyone, and everything is thoughtfully chosen and detailed on the menu. When you call yourself a wine bar, you better know your stuff, and they clearly do. Interesting French malbecs, Syrahs, etc. If we didn't have dinner reservations down the street at Penumbra, we could have stayed and tried several more. We were pleasantly surprised to be able to have our pick of seats on a lovely Saturday evening. Perhaps it's never completely packed? If so, what a great spot to have in your back pocket for a glass or two of wine and a little snack. I say little snack because if you're a vegetarian the menu is quite limited. We had a very cool mushroom and onion galette with a chevre "ice cream." The galette itself was good, but that chevre was quite an experience, absolutely delicious with rich flavors. Otherwise, however, a vegetarian might struggle a bit to go too deep into the menu for dinner. Obviously they're known for oysters and charcuterie, but I would love to be able to do something more than a few apps or a salad for dinner. Maybe that will be different as they approach these warmer months. Overall, however, Webster's remains a premiere option for some of the best wine, and friendliest service, in the city.

    Autumn B.

    Everything was incredible. Staff, wine selection, food, vibes. All of it. Had the best night with friends here and look forward to doing it again

    Salad
    Sheena P.

    Overall: 4.7/5 Food: 4.5/5 - we went in for the burger special which is only available Tuesdays/Wednesdays through April. The burger was very good - extremely flavorful and despite not being a smashburger it had great texture because they have these crispy potato matchsticks in the burger itself. The sauce was also very flavorful - the bun was extremely fluffy and lightly sweet - almost Hawaiian roll esque. No notes on the burger but the fries could have been crispier - but the sauce they came with was also very yummy. We also got the salad and it was quite nice but requires some effort because they leave some of the lettuce in large chunks - the bacon on the salad is stellar but I think overall it could have used something with more acidity or brightness. I would definitely get the burger again :) Service: 5/5 fantastic - our server was super knowledgeable about the wines and equally helpful to our seasoned wine drinkers and the novices. Ambiance: 5/5 cute, great furnishings - we actually did comment that the chairs in the back dining area where we sat were very cozy. When it's not super busy you can easily select a table so I like this back area better.

    Cheese board
    Nanette B.

    Visited Webster's twice in one day during a recent visit to Chicago. For the first visit, I was attending a tasting of Matic wines. These are wines from Slovenia that took me far from my Cabernet/Zinfandel comfort zone. Webster's hosted the tasting and also provided delicious focaccia bread, a tasty olive and cheese salad and warm eggplant hummus to line our tummies. We found ourselves back at Webster's to close out the night. This time, I enjoyed a cheese board, a local pils and great conversations with the bar staff and patrons. This is a warm, convivial spot to enjoy a good drink, elevated snacks and meet some new people.

    Charcuterie board
    Ryan B.

    Located in the corner in Logan square you have a fantastic date spot or place to come for a relaxing glass of wine. The staff are extremely friendly and the space is intimate but large enough. There is also a small sidewalk patio. There is a nice selection of wines from many areas and the staff can help guide you in your choices. The prices are good and they have a perfectly matched food menu. We decided for a New Zealand wine with a charcuterie board. It was a perfect afternoon.

    Crawfish Monica
    Yvonne I.

    The wine selection at Webster's is excellent, but the food and cocktails are also great as well. I've come here twice by myself. Since they don't typically accept reservations, I don't know if there would be a long wait for a larger group.  I would recommend coming early in the evening if you are pressed for time.  There are several high quality sparking, red, white, and sherry wines on the menu. I've had both wine and one of their cocktails (Websters Fancy Manhattan). This cocktail costs a little more than most of the other cocktails on the menu, but worth trying if you love whiskey based drinks. The liked the addition of pesto to the grilled oysters. Good appetizer option.  The burger is a 10/10. It is topped with sharp cheddar, bacon jam, shoestring potatoes, and a charred scallions aioli. I've never noticed this burger on best burgers in Chicago lists, but it definitely belongs there. I would say that this burger is on a similar level as the ones from Table Donkey and Stick and Owen and Engine.  The Crawfish Monica is a great seafood cajun dish. I learned during my second visit that the head chef has ties to New Orleans. It totally makes sense. The flavors tasted very authentic to flavors I've had during past visits to New Orleans.

    Cheese board
    Nicki C.

    Popped in randomly and although it was busy we were seated right away! Everyone is super friendly and the service is quick! We shared a bottle of the cab franc ange which was different than a usual cab franc, this was lighter but tasty! We shared a bunch of apps which were oysters, cheese board, fries, and chilled beets. The chilled beets were absolutely delicious, it was so fresh, sweet and salty, I could eat bowls of it.

    Wine and vermouth
    denise s.

    Cozy little spot good views of the action outside. Just across the street from the blue line which makes for a nice stop off to or from the city. Menu is a little limited, but the staff can help with recommendations. I was the DD and had multiple NA wines and drinks to choose from. Their outdoor tables are great in the summer.

    Emma S.

    Great local place for an upscale dinner and wine. The burger was good, golden beets are a good small plate to share with the group. Would come again and sit in the window or bar for an evening drink.

    Mike B.

    Went in here on a Saturday night and ordered a few drinks. Nothing is more annoying then watching a bartender line up the wine glass to a mark on the bar and filling your glass to that exxxxact amount. I get portion control but going about it like this is tacky. Second the other drink we ordered we asked for as a spritz. The guy said no problem, we asked if he made it with Prosecco and he said yes. The drink was actually decent. We had one drink and decided to go somewhere else after because of the large amount of drunk girls screaming at the bar. When we got the bill we handed over the credit card and just happen to notice that they charged us $15 for the drink instead of the $12 listed on the menu. When we asked about it the guy told us he didn't have Prosecco and used the higher cost champagne to make the spritz and that was $15. Now I don't care about $3, but that's not how you do business. If you don't have something you either tell the customer you don't have it. Or you make it and you eat the difference. You don't say I substituted and charged you more without asking you, even though you were sitting at the bar 2 feet away and you just confirmed you were making it with Prosecco. So congratulations you got an extra $3 from us and because of the way you handled it (annoyed and dismissive) when we asked about it, I won't be back. Penny smart, pound foolish.

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    7 years ago

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    3 years ago

    Visited about a month ago. Service is par at best. Bartenders knew little about wine and seemed annoyed about questions that were asked.

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    Page 2 of 4

    Ask the Community - Webster’s Wine Bar

    Do they serve wine flights?

    Hello! When we opened our doors almost 25 years ago, the flights were our big focus, however we now just have all of our glass pours available in "taste" sizes as well as… Read more

    Don’t See Your Question? Ask Away!

    Review Highlights - Webster’s Wine Bar

    Anne Marie deserves a raise because she dips her fries in the chicken liver mousse which is an awesome idea.

    Mentioned in 4 reviews

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    Apero

    Apero

    4.6
    (35 reviews)
    2.4 mi

    I think this is what people mean when they say something is a hidden gem. Apéro has an incredible…read morewine and vermouth selection, tasty small bites, and great cocktails. Above all, the staff here is fantastic! They're super friendly and also knowledgeable about everything on offer. I love this place but get here early as it gets packed.

    Stopped into this wine bar on a rainy Sunday right when they opened with five of my friends. They…read morewere able to seat us immediately in the spacious corner booth. The ambiance is really nice without feeling too "stuffy". Bar was gorgeous and service was friendly and helpful, allowing my boyfriend to sample some wines before going in on some bottles. Prices were what you'd expect for a trendy natural wine bar. The complimentary corn nuts in the antique dish were a cute touch. The charcuterie board with mixed meat and cheese was really small though. Only three pieces of cheese for five people... it made it feel like an awkward fight over who'd get to try some. The gluten free crackers were appreciated though. We ended up ordering more food including the "party tray" which I would describe more as charcuterie nachos. We didn't really know what to expect with this one so we got the canned mussels but it really would've tasted better with the prosciutto instead. It included a whipped cheese, olives, and cornichons piled onto potato chips. Less of a tray and more of a nacho-style dish. If we return next time we're in town, I'd skip the food and focus more on the wine. Beyond that, it was a fun time!

    Photos
    Local whisky , corn nuts, and orange wine
    Local whisky , corn nuts, and orange wine
    Menu
    Menu
    Mezcal Old Fashioned

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    Mezcal Old Fashioned
    Penumbra

    Penumbra

    4.8
    (1k reviews)
    0.4 mi
    $$$

    I had the pleasure to dine at Penumbra on a Thursday evening. We were celebrating a graduation and…read morethe staff were very welcoming when we arrived. I was visiting from out of town and was not familiar with the parking around the area. I asked one of the staff members and immediately they reassured me that the side street would raking was totally fine to park just so long as it wasn't the front of the building where you have to pay. The food started with a complementary potato soup which was flavorful and lovely. We got a round of drinks and one of our party didn't care for her drink and it was replaced no question. We had the flat iron steak, the chicken, and the salmon and each entree was wonderful. The proteins were all very tender and juicy. I was also very pleased with the salad that came first which was lightly dressed and very seasonal. We finished our dining experience with a slice of cheesecake. It was a nice cap to the end of a wonderful meal. I would recommend this restaurant for any occasion - I would love to come back and try some of the other items on their menu.

    **Hidden gem!!!**…read more Penumbra is SUPER sexy and low-key elite. This is one of those spots that will make you look like a total restaurant pro if you take someone there or recommend it. The ambiance is intimate, romantic, and just feels exclusive without trying too hard. I took my girl there for her birthday and she absolutely loved it -- which is always the real test. We had the ribeye and the Rotini Bianco, and both were excellent. The ribeye was cooked perfectly, tender and flavorful. The Rotini Bianco was rich, creamy, and done just right. Every dish felt intentional and well executed. Don't hesitate to book. If you're trying to impress or celebrate something special, this is the move.

    Photos
    Penumbra
    Penumbra
    Quesadilla

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    Quesadilla
    Volo Restaurant Wine Bar

    Volo Restaurant Wine Bar

    3.9
    (653 reviews)
    1.8 mi
    $$

    I wish that I had discovered Volo earlier because it is such a dreamy spot. The patio is totally…read morehidden from the street view and completely takes you out of the busy city feel. We sat in a cabana which was super fun. It was snowing outside and we were perfectly comfortable temperature wise without our jackets on in the patio area. This would be the PERFECT spot for a small wedding or engagement party. I had heard great things about their happy hour and it lived up to all of my expectations. We had a dozen of their $1oysters as well as some $7 spritzes. The food here was also really great! We enjoyed the whipped ricotta toast and steak tartare especially. The staff here are lovely and super knowledgeable on wine. They have over 30+ wines by the glass at any time!

    Volo Bar is such a gem. The service was excellent, and the happy hour menu is fantastic. I had the…read more$1 oysters and a red wine on draft--great quality and a really nice variety to choose from. The space itself is adorable and cozy, with a sophisticated charm that honestly reminded me of being in Italy, like a tucked-away corner bar you just stumble upon. Our server, Austin, was amazing--super attentive, friendly, and fun, which made the experience even better. Definitely ask to sit in the cabana area if you can--it's absolutely beautiful. This spot is perfect for a girls' night or a date night since it feels intimate and special. One thing to note: reservations are timed, which I didn't realize beforehand, so that part was a little awkward while catching up with friends. Overall, I loved it and can't wait to go back.

    Photos
    The view from the sidewalk.
    The view from the sidewalk.
    Fried Green Tomatoes
    Fried Green Tomatoes
    Aviation Spritz

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    Aviation Spritz
    Outside Voices

    Outside Voices

    4.3
    (55 reviews)
    0.8 mi

    If you like cute and trendy wine bars, you have to go to Outside Voices. This was my first spot on…read moremy Chicago trip visiting my best friend. We met up here. I walked from the Blue Line and felt extremely safe. It's in such a pretty part of town. There are plenty of seating spaces both inside and outside. When you arrive, you find a table you like and then go up to the counter to order. They have QR codes everywhere so you can see the menu online. If you like natural wines this is the place for you. The people who work here are absolutely incredible. I came straight from the airport so had my suitcase and one of the bartenders offered to take my bag to the back which I adored. My friend also took a really long time to get there from work so I just hung out for a while and they didn't make me feel too weird about it. One of them even gave me a generous pour of the wine I got. I also ordered us a meat and cheese board which was simple, but nice. Do know that the prices are a bit high here. If you want to get a full bottle of wine the average price is about $60 for a bottle. The aesthetics of this bar are A+. It is really loud inside. The name says it all, you will be using outside voices. While we adored this place, the music was a bit loud so it was a little hard to catch up. That being said, we made the most of it. It also was the spot that I asked her to be my bridesmaid so it'll forever have a special place in my heart. If you're looking for a cute and trendy place, with fun music blasting, and a great vibe, this is it. I highly recommend Outside Voices.

    Went for happy hour on a Friday and it was very cute! The place was a bit dead when we got there…read moreinitially but soon enough pretty much all tables were taken. They have plenty of board games and a disco diner vibe going on. Would recommend for a girls night out. Fav on the menu - dry rosé cider, fries with garlic aioli

    Photos
    Vibes
    Vibes
    Appreciating the disco ball and the interior from the bar
    Appreciating the disco ball and the interior from the bar
    Vibes

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    Vibes
    Beautiful Rind

    Beautiful Rind

    4.8
    (110 reviews)
    0.9 mi
    $$

    Still an amazing spot! We came here on an afternoon and enjoyed quiet bar service. We went with 3…read morecheese and 2 meat build of our charcuterie board. Loved all the cheeses and they were complimented with fig, strawberry and a citrus butter that was mesmerizing. I also can't say enough about the friendly service. The staff made great recommendations and answered all our questions.

    I ADORE the Beautiful Rind. It is truly the jack of all trades of a business, operating not only as…read morea restaurant, but also a store for all your charcuterie needs and a space offering a diverse array of educational, fun, and unique classes. The staff there is truly into their craft and provide the best time for all their services. I finally got to try their sandwiches after years of coming for their charcuteries and various classes (all of which you truly cannot go wrong with), and they were to die for. We split their classic grilled cheese and the TBB and they were both nothing short of phenomenal. The grilled cheese comes with tomato soup which was delicious, and you're able to choose a side for all their sandwich options (we chose arugula salad, which was perfectly lemony). My one and only suggestion would be to offer a toasted option for the TBB sandwich, but it was also truly great as is - I would definitely get both again! Also a random rec but they carry a pretty hard to find red sparkling wine that is AMAZING - Cleto Chiarli Lambrusco Amaible, must try!

    Photos
    Cheese class / tasting!
    Cheese class / tasting!
    Wine and cheese class
    Wine and cheese class
    Cheeses

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    Cheeses

    Webster’s Wine Bar - wine_bars - Updated July 2026

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