Our Favorite Spots to Drink Wine in Chicago

Chicago is a city known for its world-class shopping, the Chicago Cubs, and Chicago-style pizza. But did you know they are also a spot filled with top-quality wine bars?

red wine at chicago illinois wine bar

A good wine bar always feels like home, from the cozy, lounge-like settings to the expertly crafted cocktails and knowledgeable wine servers that frequent such spots.

It is also an excellent opportunity to spend time with friends and family and enjoy some quality conversation.

No matter what your level of experience with wine is, or even if you like wine or not, the best wine bars in Chicago deliver outstanding hospitality, quality beverages, and delicious food.

If you’re interested in learning more about the best wine bars in Chicago, the following is my summary of the best ones in the city.

Rootstock Wine & Beer Bar

954 N California Ave, Chicago, IL 60622
Phone: 773-292-1616
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On the corner of N. California Ave and W. August Blvd sits Rootstock Wine & Beer Bar, a trendy wine bar with a relaxed, lounge-like atmosphere.

Their focus is on serving small-production wine and beer, and they provide an extensive list of beverages by the glass or bottle.

My favorite part of Rootstock is the background on their menu for each wine. It not only helped me learn about what I was drinking, but it showed a commitment to their passion and philosophy.

Rootstock also serves food with their wine and beer. In addition to small plates like olives and fried almonds, they serve fantastic chorizo and kale soup, cheese and charcuterie boards, and rich, bite-size desserts.

Pops for Champagne

601 N State St, Chicago, IL 60610
Phone: 312-266-7677
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Pops for Champagne is an elegant and upscale champagne-specific bar located a couple of blocks west of the Magnificent Mile.

They have champagne selections including vintage and non-vintage champagne, rose champagne, grower-producer champagne, and

In addition to a variety of delicious champagne, Pops for Champagne also offers a wide selection of whiskey and scotch, cognac, red and white wine, and craft cocktails.

They serve a variety of bar snacks to go with your cocktail or glass of champagne. I recommend the Pork Belly Bao Buns or the East Coast Oysters.

They also offer a delightful trio of macarons with strawberry champagne, raspberry chocolate, and milk chocolate truffle flavor options.

All Together Now

2119 W Chicago Ave, Chicago, IL 60622
Phone: 773-661-1599
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All Together Now is a charming restaurant and wine store designed for friendly gatherings. The shop is located in Chicago’s Ukrainian Village and is a warm, well-lit space perfect for wine and cheese tastings, classes, or grabbing a tasty meal.

At All Together Now, patrons can enjoy homemade bagels, fruit preserves, and crackers in addition to their wide selection of cheese.

Small plates range from soups, dips, and charcuterie snacks to hearty sandwiches, meatballs and farina, or crispy chicken confit. I highly recommend the ricotta tortellini, paired with any of their 150+ bottles of wine.


3309 W Fullerton Ave, Chicago, IL 60647
Phone: 773-772-2343
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Chicago’s Logan Square is home to the wine bar Penumbra. Here, Latin-inspired American fare can be enjoyed in a cozy, dimly lit atmosphere perfect for a romantic evening or a special celebration with friends and family.

Patrons can also enjoy a wide selection of charcuterie plates, seafood, or heart steak and pork dishes with their wine.

I highly recommend you finish your meal with the Molten Brandy Truffle, a flourless lava cake that is infused with chocolate Brandy truffle and topped with a raspberry Grand Marnier sauce.

The Press Room

1134 W Washington Blvd, Chicago, IL 60607
Phone: 331-240-1914
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The Press Room is one of my favorite wine bars in Chicago. They are located across the street from the Hyatt House Chicago in a hundred-year-old building that throughout its life has been a publishing house, a casket factory, and a holography museum.

The space is moody and has a vintage feel that goes along with the vibe of the historic building.

You can experience everything from hand-shucked raw oysters to intricate pasta and steak dishes here.

I recommend the Butternut Squash Stracci with any of their shaken or stirred cocktails. They also have an extensive list of spirits, beer, and wine by the glass.

They offer private dining options for special occasions, a wine club, and a happy hour from 4-6 pm every Tuesday and Wednesday, where you can enjoy $7 cocktails and $1 raw oysters.

Webster’s Wine Bar Chicago

2601 N Milwaukee Ave, Chicago, IL 60647
Phone: 773-292-9463
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Wine purists will love both the wine and the philosophy at Webster’s Wine Bar. Since 1994, the team at Webster’s has made it their mission to serve wine from small, family-owned wineries that are crafted with care and passion.

They prefer to serve wines without additives or chemicals and believe that doing so allows the true flavor of the wine to shine. In addition to countless high-quality wines, they offer a variety of craft cocktails and spirits.

If you stop by for dinner, I highly recommend you try the Croque Monsieur Tartine or the Webster’s Burger. You can find Webster’s Wine Bar in the heart of Logan Square.

Lush Wine & Spirits

Multiple locations
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Lush Wine & Spirits has several locations scattered throughout Chicagoland, including a spot on Chicago Avenue, one in Roscoe Village, and a third on Central Street Evanston.

Each location is a place where people go to learn about and purchase wine from friendly, welcoming experts.

They serve a healthy mix of wine, draft beer, cocktails, and delicious food at each location. Offerings tend to vary by location; however, during my visit to the Chicago Avenue spot, I tried an incredible Sazerac and a Drop The Mic Burger.

For dessert, they offer homemade smores and hand-made chocolate bars, both of which are to die for.

Red & White Wines

1861 N Milwaukee Ave, Chicago, IL 60647
Phone: 773-486-4769
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Red & White Wines are stationed in the Bucktown neighborhood and has been serving up artisanal wines to their guests since 2008.

Their wine bar is a cool spot to hang out with a date or friends, and they also offer wine tastings on Saturday afternoons. They offer wines produced all over the world and at a range of prices.

New wines come in all of the time at Red & White Wines. I splurged on a bottle of Meinklang, Morgen ‘20 and a bottle of Franck Balthazar, Cotes Du Rhone ‘20.

Vol. 39

39 S LaSalle St #200, Chicago, IL 60603
Phone: 312-604-9909
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If you’ve ever dreamt of sipping an old-world wine in a stately, candle-lit library, Vol. 39 is the spot for you.

This unique wine bar is shrouded in a lovely atmosphere, from the tufted leather couches to the crystal light fixtures.

They serve up delicious craft cocktails and luxurious wines, emphasizing beverages from the mid-20th century. Guests can also enjoy small plates with their drinks.

Vol. 39 has won several local and national awards for their expertly crafted drinks, ranging from best cocktail to best bar. They are located on the second floor of The Kimpton Gray Hotel in Chicago’s Loop.

Printers Row Wine Bar and Shop

719 S Dearborn St, Chicago, IL 60605
Phone: 312-663-9314
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Located in the South Loop. Printers Row Wine Bar and Shop is a charming local spot that has been in business since 2004.

Here you can enjoy your favorite craft beer, a glass of phenomenal wine, or a variety of spirits and cocktails. The bar itself is gorgeous, from the intricate tin ceiling to the book-lined bar wall.

There is a wide variety of unique wines to sample, which can be enjoyed by the bottle or the glass.

They also offer Bistro Style Wine, which is an affordable way to enjoy three basic wines on draft in a glass pour or a carafe.

While I was in town, I stopped by Printers Row for a glass and a snack. I enjoyed a bold glass of Pas Curtei, Carinana Blend with the Midwestern House Board.

Volo Restaurant Wine Bar

2008 W Roscoe St, Chicago, IL 60618
Phone: 773-348-4600
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In my opinion, Volo Restaurant Wine Bar has one of the most beautiful outdoor patios in the entire city.

The restaurant is located in Roscoe Village between the Shangri-La Vintage clothing store and Roscoe Village Bikes.

It successfully combines urban, vintage, and boutique styles to create an effortlessly cozy atmosphere, perfect for intimate wedding receptions or date nights.

In addition to the gorgeous backyard garden with its private cabanas and chic bistro seating, Volo offers a full bar and a list of small plates and charcuterie items.

They have 30 wines available at any one time and offer a seasonal food menu that includes locally grown and organic ingredients.

I had to make a reservation to snag a spot on the magical back patio, which was worth it. I enjoyed a B.M.G. Flatbread to start, followed by the 8-ounce Beef Tenderloin.

For dessert, I highly recommend you try the Salted Caramel Chocolate Mousse paired with the Cascina Bonfante from Italy.

J9 Wine Bar

1961 N Halsted St, Chicago, IL 60614
Phone: 312-982-2488
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J9 wine bar was designed to be a warm and welcoming place where people of all walks of life could gather to enjoy a good glass of wine and good conversation.

It’s a beautifully decorated restaurant with warm, ambient lighting and cozy nooks.

J9 offers a selection of regional and international wines, as well as retail wines. If you’re not in the mood for a glass of wine during your visit, they also offer classic cocktails like a Dark & Stormy or the Negroni as well as beer.

They also offer semi-customizable charcuterie boards with a selection of meat and cheeses.

Frasca Pizzeria & Wine Bar

3358 N Paulina St, Chicago, IL 60657
Phone: 773-248-5222
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I recommend stopping by Frasca Pizzeria & Wine Bar for a more Italian influence. The name comes from the Italian word for “branch,” which signified the sale of wine and food inside when hung over a farmhouse door. It was intended to be a special place for family and friends to gather to eat and drink.

Frasca Pizzeria & Wine Bar is open daily for dinner and on the weekends for brunch. In addition to authentic Italian entrees like Carbonara or Conchiglie, they offer incredible wood-fired pizzas.

During my visit, I tried the Rustica pizza, a crispy thin crust pizza topped with prosciutto, oven-dried tomato, basil, and two different types of cheese.

Figo Wine Bar

3207 N Sheffield Ave, Chicago, IL 60657
Phone: 312-819-6111
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At Figo Wine Bar, you get to experience all of the qualities of an authentic Italian wine bar while sampling wine and signature dishes from all over the globe.

They offer a limited selection of sparkling and rose wine and a robust selection of red and white wine by the glass or the bottle.

The food here is incredible, as is the expertly prepared wine list and craft cocktails that accompany it.

All of their pasta is made in-house, and they prepare their dishes with locally sourced ingredients.

The food is eclectic, from stuffed dates in gorgonzola sauce and grilled octopus to beautiful hangar steaks prepared in a Mexican Chimichurri sauce.

The best wine bars in Chicago are comfortable and cozy spots that offer a momentary escape from the bustling city.

Whether you’re new to wine or a long-time sommelier, there are spots all over the city that deliver incredible wine and satisfying meals to accompany them.

If you’d rather enjoy your glass of wine with a view, check out Chicago’s rooftop bars on our list here.

Looking to try expertly made Japanese sushi in Chicago? Check out our list of the best sushi restaurants in the Windy City.

Did we leave a Chicago wine bar out of this list? Make sure you leave us a comment and we’ll check it out!

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Written by Brian Nagele

Brian has over 20 years experience in the restaurant and hospitality industry. As a former restaurant owner, he knows about running a food business and loves to eat and enjoy cocktails on a regular basis. He constantly travels to new cities tasting and reviewing the most popular spots.