10 Best Places to Drink Wine in Chicago

1. Enolo Wine Cafe

Enolo Wine Cafe is a River North wine bar that specializes in wines by the glass. At any given time, it features around 25 different options, which is more than the full wine list at a lot of places. The wines rotate seasonally, so you’ll always find a perfect glass that fits the mood and the weather. The food is also great, and obviously pairs well with the wines.

Where: 450 N Clark St, Chicago, IL 60654

2. Rootstock Wine & Beer Bar

Rootstock Wine & Beer Bar is a brasserie in the Humboldt Park neighborhood that serves great food and wine with no pretension. Reservations aren’t accepted, which makes for a casual vibe. The wine list focuses on small-production wines — especially those made with organic and biodynamic farming practices. You probably won’t recognize a lot of bottles, which would be intimidating if not for the friendly and knowledgeable staff always ready to help without pressuring you or upselling.

Where: 954 N California Ave, Chicago, IL 60622

3. Red & White

Bucktown-based Red & White was one of the first natural wine shops in the US when it opened in 2008, and its focus hasn’t wavered. This wine shop and bistro only sells wines from vintners who use no chemicals, harvest by hand, and use native yeast strains. You can take home a bottle or enjoy a glass at the bar, where small plates that pair with the wine selection are served.

Where: 1861 N Milwaukee Ave, Chicago, IL 60647

4. Bar Pastoral

If you’re in the Lakeview neighborhood and looking for great wine, Bar Pastoral is the place to be. With an impressive wine list and an equally solid list of cheeses, you can enjoy what feels like an infinite number of pairings. The entrees are excellent as well. If you’re looking to sample a number of wines, you can order by the half pour to pair with the many cheeses and charcuteries. If you find a bottle that you especially love, it can be bought at the Pastoral shop next door.

Where: 2947 N Broadway, Chicago, IL 60657

5. Avec

If you ask Chicago chefs where they love to eat and drink wine, you’ll probably hear Avec pretty often. This West Loop neighborhood bistro from legendary restaurateur Paul Kahan does delicious Mediterranean shared plates and wines from small producers that are described as “hearty peasant wines.” All are high-quality table wines that are priced well and served without pretension.

Where: 615 W Randolph St, Chicago, IL 60661

6. Café Marie-Jeanne

Humboldt Park-based Café Marie-Jeanne makes this list not because of a huge wine list, but because it’s just such a delightful place to drink wine. Being here feels like you’re in a neighborhood brasserie in France. Neighbors stop in to buy pastries and baguettes or grab a coffee, while diners eat some of the least pretentious cuisine you’ll find in the city. The few select wines are all available by the glass or bottle, and are thoughtfully selected to pair well with the menu.

Where: 1001 N California Ave, Chicago, IL 60622

7. Webster’s Wine Bar

Originally located in Lincoln Park and now in Logan Square, Webster’s Wine Bar is one of Chicago’s original spots for wine lovers. It prides itself on having a list that is approachable enough for newbies or casual wine drinkers, but deep enough to keep the connoisseurs interested. Webster’s also has a nice selection of small plates and well-priced tasting pours that let you sample from up and down the list.

Where: 2601 N Milwaukee Ave, Chicago, IL 60647

8. Income Tax

Income Tax probably doesn’t sound like your idea of a good time, but if you love wine, this Edgewater bar will warm you up to the idea. With one of the city’s best wine lists, and a menu full of wine-friendly foods, Income Tax is a perfect place to try something new. The dark wood, exposed brick, and neighborhood location far from downtown only add to the ambiance.

Where: 5959 N Broadway, Chicago, IL 60660

9. The Press Room

Located down in the basement of the Publishing House, a West Loop boutique bed and breakfast, The Press Room is a wonderful little wine bar doing food and drinks with a trendy vibe and neighborhood ambiance. It features an amazing 40 wines by the glass and many, many more by the bottle.

Where: 1134 W Washington Blvd, Chicago, IL 60607

10. Piccolo Sogno

Piccolo Sogno, which means “little dream” in Italian, has some of the city’s best Italian food and serves it up in a slightly old-school setting. A list of over 400 wines, mainly from Italy, and a knowledgeable staff to recommend pairings makes Piccolo Sogno a little dream for lovers of Italian food and wine.

Where: 464 N Halsted St, Chicago, IL 60642