Fun Wine Bars to Try in Chicago

Disclosure of Material Connection: Some of the links in the post above are "affiliate links." This means if you click on the link and purchase the item, I will receive an affiliate commission. Regardless, I only recommend products or services I use personally and believe will add value to my readers. I am disclosing this in accordance with the Federal Trade Commission's 16 CFR, Part 255: "Guides Concerning the Use of Endorsements and Testimonials in Advertising."

Are you looking for a wine bar to try out in Chicago? The best part is there are no shortage of wine bars in the Chicago area. In fact, there are so many wine bars to try in Chicago, it’s going to be hard to narrow them down. Wine bars are great because they focus on wines.

Wine bars come down to finding one that you like. All of the wine bars are amazing, but which one do you feel most comfortable with? Chicago is such a big city, it can be hard to find which wine bars are worth going to.

Fun wine bars to visit in Chicago | The best places to drink wine in Chicago, perfect for a girls night out, date night, fun night with friends or place to take clients. Enjoy the bar scene in Chicago with these delicious wines, including a dedicated #champagne bar! | #winetasting #wine #chicago #illinois #travel #bar

Here are 8 fun wine bars to try in Chicago

You see, there are all types of wines out there. Certain wine bars might focus on Italian wines, American, or the best – sparkling wines from the world over. The options are endless! You might find a wine bar that serves vintage wine or a wine bar that serves small plates with their wine.

404 Wine Bar

404 Wine Bar

How cool is this name for a wine bar? It’s said that this wine bar also has many great specials. Some of those specials include half- price cocktails on Thursdays. I mean, no one turns their nose up to really cheap cocktails. Do they? This wine bar is also known for its really good food. I even hear that there is a fire place at the 404 Wine Bar. Sign me up!

Wine bars may be plentiful in Chicago, but if you want the real deal, this is it. You can come here, enjoy some wine, and then get on with your day. The atmosphere is cozy and the perfect place to enjoy a glass of wine.

Red & White 

The Red & White Wines bar takes pride in serving wines from vineyards where the winemakers avoid pesticides and chemicals, ones who harvest by hand. The taste of the wines will reflect this attention to detail and attentiveness. You are sure to experience high quality and luxurious wines here.

The atmosphere is reminiscent of an art gallery, rather than a bar or restaurant, giving a boutique feel. Walk around and admire the bottles of wine while you sip your own, and immerse yourself in the environment. They host a wine tasting on Saturdays and also offer a wine club that will provide you with three new wines each month. Their attention to detail spills into every area of their wine bar.


Enolo Wine Cafe

Enolo Wine Cafe

Are you looking for an interesting wine bar to check out in Chicago, Illinois area? Enolo Wine Cafe is where it’s at. Here, the wines are rotate seasonally. You can enjoy almost any glass of wine at any time. All you need to do is show up and enjoy! Tasting wine doesn’t get much better than this.

Sometimes there is nothing better than finding a new wine bar. Enolo Wine Cafe has great reviews, amazing wine, and famous dishes to match. Now you just have to figure out what your favorites are going to be.

The Press Room 

There are a lot of browns and blacks in The Press Room. It gives off a feeling of calm and relaxation, but a typical “bar” feeling at the same time. The Press Room serves foods you are familiar with, but in an enlightening way that will delight your taste buds.

They offer all kinds of wines and cocktails that you can choose from, depending on your tastes or what you want to give a try. Happy hour happens Mondays through Thursdays from 4-6pm. They also offer the Fourth Estate Wine Club, where you get a wine each month to try and they email you when it’s ready. It’s a unique opportunity to give other wines a try with experts to help select them for you.

Webster Wine Bar

Webster Wine Bar

When you go to a wine bar, it’s because you want to try wine. Well, you can drink all the wine you want when you hit up Webster Wine Bar in Chicago. This is one of the original wine bars in Chicago and continues to be one of the best. Here, you’ll find a 5 page long list of wines to try. I mean, does life even get better than this?

Webster Wine Bar has some of the top ratings in Chicago. They know how to please their guests and offer the best wine on the market. When you want to enjoy wine, come here!

Volo Wine Bar 

Despite the darker tones inside the bar, the Volo Restaurant Wine Bar has an airy atmosphere. There are many seating choices as well. You can sit at the bar, in a booth, or outdoors. No matter where you sit, you are likely to feel light and airy like the atmosphere itself, as if any cares and worries were left behind. Not only can you go whenever they’re open, but they also host events on a regular basis.

It is a great place to meet a friend, colleague, or maybe even get to know someone new. You can feel comfortable having a variety of conversations while enjoying the scenery and your choice of wine. When it comes to wine, there are fifty choices of boutique wines to choose from. Thirty of them are available to drink by the flight, glass, half glass, and ⅓ bottle carafe.

Pops for Champagne

Pops for Champagne

A wine bar can serve exclusively sparkling wine, right? Well, I guess it depends on the day of the week. But, Pops for Champagne may be the next wine bar you check out, while you’re in Chicago. Every Sunday through Thursday, you can also enjoy live jazz. Other days of the week, there are $1 oysters and more than 140 different types of champagne to try. YUM!

I personally love this venue because their main focus is on Champagne. And yes, I mean Champagne. They have a selection of Grower Producer separated by region, NV, vintage, sparkling, sweeter dosages, rosés and a selection of still and fortified wines.

Not a lot of wine bars focus on champagne, so if this is your type of thing, make sure you hit it up.



If you want to try a wine bar in Chicago that was created on a smaller scale, then you need to check out Rootstock. The focus here is on French and Italian wines. Word has it that they even have Sunday brunch here. So, in reality, you can enjoy this place all week. Go ahead and check out Rootstock, I think you’ll love it.

I can just picture myself walking into Rootstock, picking out an appetizer and trying a new wine. The atmosphere is cozy and makes a great destination after a long day of work.

DOC Wine Bar

DOC Wine Bar

When you want an authentic wine bar in the Chicago area, make sure you check out the DOC Wine Bar. This amazing acronym stands for Italy’s Denominazione di Origine Controllata. Grab a bottle of wine, yes I said bottle, and some of your favorite dishes and ENJOY the DOC Wine Bar.

I think the acronym of this wine bar is what makes it my favorite in the Chicago area. When you start with the naming, you know it’s going to be a good one.



Located in Chicago, you can check out wineHouse for special wines. This is such a unique wine experience. You can join their Wine Club, buy wine at the store, or sit back and relax and enjoy wine at their location. It’s safe to say that this place is all about the wine.

wineHouse has special events you can attend too. There’s all sorts of opportunities to take pairing classes and hang out with more wine lovers like yourself. The more wine you try and study, the more you will learn about it.


Disotto Enoteca

Interested in a fancier wine bar experience? I think you’re going to love the Disotto Enoteca. This is a late night wine-focused restaurant. This is the place you can go when you decide it’s late, but you still want to enjoy some wine.

Since this a wine-focused restaurant, you get to eat and try fancy and not-so-fancy wines. The decor is cellar-style, which is really neat. I could sit here all day and enjoy wine! Let’s face it, this wine bar also has the coolest name too. You get to say you had wine at the coolest wine bar in Chicago.

Trying wine in the Chicao, Illinois area is a privilege. The population of this city ensures that there are plenty of various wine bards to try. Whether you’re craving fancy wines or are interested in some champagne, there is something for everyone here.

For more places to go wine tasting:

 Fun wine bars to visit in Chicago | The best places to drink wine in Chicago, perfect for a girls night out, date night, fun night with friends or place to take clients. Enjoy the bar scene in Chicago with these delicious wines, including a dedicated #champagne bar! | #winetasting #wine #chicago #illinois #travel #bar

Fun wine bars to visit in Chicago | The best places to drink wine in Chicago, perfect for a girls night out, date night, fun night with friends or place to take clients. Enjoy the bar scene in Chicago with these delicious wines, including a dedicated #champagne bar! | #winetasting #wine #chicago #illinois #travel #bar

Scroll to Top