After attending countless tastings and trying numerous varieties, I've compiled a list of the best wine experiences in Chicago. From cozy neighborhood spots to upscale destinations, I've reviewed 12 different wine tastings that will suit any palate and budget.

So if you're looking for a fun night out or just want to expand your wine knowledge, read on for my top picks of the best wine tasting in Chicago. Cheers!

Le Midi Wine

Le Midi Wine
🗺️ 2108 W Division St, Chicago, IL 60622
☎️ 773-303-4884
🌐 Website
Sunday: 12–6 PM
Monday: Closed
Tuesday: 12–10 PM
Wednesday: 12–10 PM
Thursday: 12–10 PM
Friday: 12–11 PM
Saturday: 12–11 PM
Elegant environment
Tasty small bites
Unique wines by the glass
Intimate and relaxed atmosphere

The moment I walked in, the elegant environment took my breath away. It was like stepping into a cozy French bistro where I could relax and enjoy my wine. The staff were incredibly friendly and knowledgeable, making me feel right at home.

One of the things that set Le Midi Wine apart from other tastings was their tasty small bites. The food perfectly complemented the wines and gave me a chance to cleanse my palate between tastings. The menu had a great selection of cheeses, charcuterie, and small plates that were all crafted to pair with the wines.

The unique wines by the glass offered an opportunity to try something new and different without committing to a full bottle. They had an extensive selection of French wines that were carefully curated by their sommelier. Each wine had its own story and characteristics that made it special.

Finally, the intimate and relaxed atmosphere made me feel like I was in someone's personal wine cellar rather than a public tasting room. It was quiet enough to have conversations about each wine but lively enough to enjoy the company of others.

Overall, Le Midi Wine is definitely one of the best wine tastings in Chicago!

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WC Winery & 25 Boccè

WC Winery & 25 Boccè

First off, the atmosphere was inviting and sophisticated. The wine selection was extensive, featuring a variety of reds, whites, and rosés. But what really set this place apart was their boccè court! I mean, who doesn't love a good game of boccè with their wine? Plus, the staff was knowledgeable and helpful in guiding me through my tasting. Overall, if you're looking for an enjoyable experience that goes beyond just drinking wine, WC Winery & 25 Boccè is definitely worth checking out.

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Bronzeville Winery

Bronzeville Winery
🗺️ 4420 S Cottage Grove Ave, Chicago, IL 60653
☎️ 872-244-7065
🌐 Website
Sunday: 10 AM–2:30 PM
Sunday: 4–10 PM
Monday: Closed
Tuesday: Closed
Wednesday: 4–10 PM
Thursday: 4–10 PM
Friday: 4–11 PM
Saturday: 4–11 PM
Art-filled and gorgeous decor
Fantastic food menu
Above-and-beyond staff
Reasonable prices for quality
Live house DJ

First, let me just say that the decor of this place is absolutely stunning. The walls were covered with beautiful artwork and the overall atmosphere was very chic and sophisticated. I could tell right away that this was a place where people come to enjoy a good glass of wine.

As for the wine selection, they had a great variety to choose from! I tried several different wines and each one was better than the last. The prices were also very reasonable considering the quality of wine they offered.

But what really stood out to me about Bronzeville Winery was their food menu. It was fantastic! They had everything from charcuterie boards to small plates like truffle fries and sliders. Honestly, I could have spent all night just eating their delicious food.

Another thing that really impressed me was their staff. They went above-and-beyond to make sure that my experience was unforgettable. They were knowledgeable about the wines and even offered suggestions based on my preferences.

To top it off, there was a live house DJ playing music which added to the already lively atmosphere.

Overall, Bronzeville Winery is definitely one of my top picks for best wine tasting in Chicago! If you're looking for a place with great wine, amazing food, and an awesome vibe - this is it.

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Uvae Fromagerie & Tasting Room

Uvae Fromagerie & Tasting Room
🗺️ 5553 N Clark St Unit 2, Chicago, IL 60640
☎️ 773-654-1432
🌐 Website
Sunday: 1–8 PM
Monday: 1–8 PM
Tuesday: 12–9 PM
Wednesday: 12–9 PM
Thursday: 12–9 PM
Friday: 12–9 PM
Saturday: 12–9 PM
Modern-rustic decor
Great wine deals
Excellent service
Thoughtful curation

As soon as I walked into Uvae, I was struck by the modern-rustic decor that set the perfect ambiance for a wine tasting. The lighting was dim, yet warm, and it felt like an intimate space where you could really enjoy the wine without any distractions.

Speaking of wine, Uvae offers some great deals on their selection. Not only do they have a variety of options to choose from, but they also offer different flights and specials that are definitely worth trying out. Plus, their servers are incredibly knowledgeable about the wines and can help guide you towards something that will suit your taste buds.

The excellent service didn't stop there - the staff was attentive and friendly throughout my visit. They were happy to answer any questions we had about the wines or cheeses and made us feel welcome in their space.

Finally, I have to give credit to the thoughtful curation of their wines and cheeses. Each selection seemed intentional and well-paired with its counterpart. It added an extra layer of sophistication to the experience.

Overall, I highly recommend Uvae Fromagerie & Tasting Room for anyone looking for a unique and enjoyable wine tasting experience in Chicago. Between the atmosphere, great deals on wine, excellent service, and thoughtful curation - this place has it all!

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Picnic Wine & Provisions

Picnic Wine & Provisions
🗺️ 7301 N Sheridan Rd, Chicago, IL 60626
☎️ 773-856-0000
🌐 Website
Sunday: 1–7 PM
Monday: Closed
Tuesday: Closed
Wednesday: 3–7 PM
Thursday: 3–8 PM
Friday: 3–8 PM
Saturday: 1–8 PM
Great beverage selection
Indoor and outdoor seating
Affordable wine options
Knowledgeable staff

As soon as I walked in, the first thing that caught my attention was their great beverage selection. It wasn't just wine, they also had a variety of craft beers and ciders to choose from too. The atmosphere was warm and inviting, with both indoor and outdoor seating available.

One thing that really stood out to me was the affordable wine options. They had a wide range of prices so there was something for everyone's budget. And if you're unsure about what to get, the staff is extremely knowledgeable and can help guide you towards the perfect choice.

What I appreciated most about Picnic Wine & Provisions was the laid-back vibe. It's not pretentious or stuffy like some other wine bars can be. You can come here dressed up or dressed down and still feel comfortable.

Overall, Picnic Wine & Provisions is a great spot for those who want to enjoy a glass of wine without breaking the bank or feeling intimidated by fancy decor. With their great beverage selection, indoor/outdoor seating options, affordable prices, and knowledgeable staff - it's no wonder why this place is one of my top picks for best wine tasting in Chicago!

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WineStyles Norwood Park

WineStyles Norwood Park
🗺️ 6182 N Northwest Hwy, Chicago, IL 60631
☎️ 847-518-9463
🌐 Website
Sunday: Closed
Monday: Closed
Tuesday: 2–9 PM
Wednesday: 2–9 PM
Thursday: 12–9 PM
Friday: 12–9 PM
Saturday: 12–9 PM
Wonderful Atmosphere
Educational Tastings
Cheese Board for Parties
Friendly Service
Delicious Wines

First of all, the atmosphere was simply wonderful. The lighting was just right and the decor made me feel like I was in a chic wine bar in Paris. The ambiance was perfect for enjoying a glass of wine with friends or even for a romantic date night.

The tastings were also incredibly educational. The staff took the time to explain each wine and its tasting notes, which really enhanced my appreciation for each one. I felt like a true connoisseur after leaving WineStyles Norwood Park!

One thing that stood out to me was their cheese board. It's perfect for parties and pairs perfectly with their wines. I'm already planning my next get-together there!

The service was friendly and attentive without being overbearing. They were happy to answer any questions I had and made sure my experience was enjoyable.

Finally, let's talk about the wines themselves! Delicious doesn't even begin to describe them. Each one had its own unique flavor profile that left me wanting more.

Overall, WineStyles Norwood Park is definitely one of the best wine tastings in Chicago. Whether you're a seasoned wine drinker or just starting out, this place has something for everyone. Don't miss out on this gem!

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VIN312 Winery

VIN312 Winery
🗺️ 4710 N Ravenswood Ave, Chicago, IL 60640
☎️ 312-714-5050
🌐 Website
Sunday: 2–6 PM
Monday: Closed
Tuesday: Closed
Wednesday: Closed
Thursday: Closed
Friday: Closed
Saturday: 2–6 PM
Wine making on-site
Attentive bartender
Great hospitality
Quality wine tastings
Meet the winemaker

From the moment I arrived, I was impressed with its cozy atmosphere and the sight of the wine making process happening on-site. The attentive bartender greeted me with a warm smile and offered to walk me through their wine selection.

The hospitality at VIN312 Winery was top-notch! The staff took their time to explain the different types of grapes used in their wines and provided detailed descriptions of each wine's flavor profile. They even allowed me to meet the winemaker, who shared his passion for winemaking and his love for Chicago.

But let's talk about the wine tastings! Each pour was carefully measured out, allowing me to fully experience every sip without feeling rushed or overwhelmed. The quality of each wine was exceptional, with bold flavors that tantalized my taste buds.

Overall, I highly recommend VIN312 Winery for anyone looking for a memorable wine tasting experience in Chicago. With its combination of great hospitality, quality wine tastings, and an opportunity to meet the winemaker, it's truly one-of-a-kind. So why not step out of your comfort zone and give VIN312 Winery a try? You won't regret it!

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City Winery Chicago

City Winery Chicago
🗺️ 1200 W Randolph St, Chicago, IL 60607
☎️ 312-733-9463
🌐 Website
Sunday: 12–9 PM
Monday: 4–9 PM
Tuesday: 4–9 PM
Wednesday: 4–10 PM
Thursday: 4–10 PM
Friday: 4 PM–12 AM
Saturday: 12 PM–12 AM
Intimate performances
Simple food & wine menu
Hosted table seating
Excellent acoustic setup

The ambiance of City Winery is perfect for a cozy night out with friends or an intimate date. What sets it apart from other wineries in Chicago is its unique combination of wine tasting and live performances. The intimate performances make the experience even more special, and the seating is arranged in such a way that you feel like you're part of the show.

The food menu at City Winery is simple yet satisfying, and pairs perfectly with their wines. The simple food & wine menu lets you focus on what matters most - enjoying the taste of delicious wines while indulging in tasty bites.

The hosted table seating arrangement adds to the inviting atmosphere. It's easy to strike up a conversation with your neighbor, who could be someone who shares your love for wine or just someone new to explore the flavors with you.

The acoustic setup at City Winery is top-notch, making it an excellent venue for live music events. The sound quality is simply amazing! I was blown away by how well balanced and clear the music sounded. Excellent acoustic setup makes all the difference!

Overall, my visit to City Winery Chicago was a delightful experience that I would recommend to anyone looking for an unforgettable wine tasting adventure. Don't forget to check out their upcoming events calendar too!

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Wild Blossom Meadery and Winery

Wild Blossom Meadery and Winery
🗺️ 9030 S Hermitage Ave, Chicago, IL 60620
☎️ 773-840-4642
🌐 Website
Sunday: 12–9 PM
Monday: 3–9 PM
Tuesday: 3–9 PM
Wednesday: 3–9 PM
Thursday: 3–9 PM
Friday: 3–11 PM
Saturday: 12–11 PM
Cozy and picturesque
Interesting mead menu
Knowledgeable staff
Exceptional service

Firstly, the atmosphere was cozy and picturesque, perfect for a romantic date or a casual catch-up with friends. The menu was unique with an interesting selection of mead that I had never seen before. The knowledgeable staff was incredibly helpful in explaining the differences between mead and wine, which made me appreciate the tasting even more.

The exceptional service was also worth mentioning. The staff went above and beyond to ensure we had a great experience, from providing us with personal recommendations to ensuring our glasses were always full.

One standout feature of Wild Blossom Meadery and Winery is their mead selection. While most places stick to traditional wine options, Wild Blossom offers something different for those looking for a change of pace. Their honey-based drinks are delightful and refreshing.

Overall, my experience at Wild Blossom Meadery and Winery was fantastic - great atmosphere, unique menu, knowledgeable staff, exceptional service - everything you'd want in a wine tasting experience. I highly recommend giving it a try and experiencing something new like mead!

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Chicago Winery

Chicago Winery
🗺️ 739 N Clark St, Chicago, IL 60654
☎️ 312-763-3674
🌐 Website
Sunday: 10:30 AM–10 PM
Monday: 5–10 PM
Tuesday: 5–10 PM
Wednesday: 4–10 PM
Thursday: 4–10 PM
Friday: 4 PM–12 AM
Saturday: 10:30 AM–12 AM
Affordable prices
Delicious food and wine
Friendly staff
Private event venue
Chefs Whim worth trying

Upon arriving, I was impressed with the affordable prices of their wine tastings. As someone who has visited many wineries, I know that prices can often be sky-high, but Chicago Winery offers a great value for their high-quality wines.

But what really made my visit to Chicago Winery stand out was the delicious food and wine pairing options. The chefs Whim is a must-try option for anyone who appreciates good food and wine. The flavors of each dish enhanced the taste of each wine, creating a perfect harmony in my mouth.

I also appreciated the friendly staff who were knowledgeable about the different wines and provided great recommendations based on my preferences. They made me feel at home and comfortable throughout my visit.

Another highlight of Chicago Winery is that it doubles as a private event venue, making it perfect for special occasions or corporate events. It's definitely worth considering if you're looking for an intimate setting with great wine and food.

Overall, I highly recommend Chicago Winery to anyone looking for a fantastic wine tasting experience in Chicago. The combination of affordable prices, delicious food and wine pairings, friendly staff, private event venue option, and chefs Whim make it one of the best options in the city.

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Red & White Wines

Red & White Wines
🗺️ 1861 N Milwaukee Ave, Chicago, IL 60647
☎️ 773-486-4769
🌐 Website
Sunday: 12–8 PM
Monday: Closed
Tuesday: 12–8 PM
Wednesday: 12–8 PM
Thursday: 12–8 PM
Friday: 12–10 PM
Saturday: 12–10 PM
Wide variety of natural wines
Best monthly wine club
Friendly and helpful staff
Free weekly tastings for wine club members
Discount on 6-pack purchases

First of all, I was blown away by the wide variety of natural wines they offer. I'm talking about some serious juice here! From bold reds to crisp whites, they have something for every palate.

But what really caught my attention was their monthly wine club. Not only do you get access to exclusive bottles, but you also get free weekly tastings! And let me tell you, the staff is incredibly friendly and helpful. They are more than happy to guide you through your tasting experience and answer any questions you may have.

As a wine club member, I also received a discount on 6-pack purchases, which is perfect for stocking up on my favorite bottles. But even if you're not a member, their prices are more than reasonable for the quality of wine they offer.

Overall, Red & White Wines is definitely a top contender for the best wine tasting in Chicago. Their dedication to natural wines and excellent customer service make for an unforgettable experience. So grab your glass and head on over – this place is worth it!


Knowledgeable and friendly staff
Cool atmosphere with great vibe
Small producers with unique stories
Offers wine membership options
Subscription service with amazing wine

First and foremost, the staff at Winestyr was incredibly knowledgeable and friendly. They were happy to answer any questions I had about the wine selection and even recommended some fantastic options. The atmosphere of the place was also noteworthy with its cool vibe that makes you want to stay for hours.

One of the things I loved most about Winestyr is their focus on small producers with unique stories. It's refreshing to taste wines that have a backstory, and it adds depth to the experience. Plus, they offer wine membership options which are perfect if you're a regular patron.

But what really set Winestyr apart from other wine tastings in Chicago is their subscription service. I signed up for it on a whim and let me tell you - the wine they send out is nothing short of amazing! Each bottle had its own character and story, which made each shipment feel like a special occasion.

Overall, I highly recommend Winestyr for anyone looking for an incredible wine tasting experience in Chicago. Whether you're a seasoned sommelier or just starting out, there's something here for everyone!

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Alex Irvin

Alex enthusiastically explores her hometown of Chicago with an adventurous spirit and a pen in hand. As a freelance writer, Alex specializes in reviewing places in and around the city. From restaurants to theaters, Alex brings attention to interesting finds throughout the area. Along with her reviews, Alex writes articles on Chicago's neighborhoods, engaging events, and her own travel stories. When Alex can't be found behind a computer, you'll find her sampling the newest restaurant, attending a play or strolling around the city.