Chicago dining is more than just Italian beef, deep dish pizza, chophouses and celery salt–sprinkled, Chicago-style hot dogs. The Second City has evolved into one of America’s central culinary scenes, and one of its most dynamic. Man cannot live off of Malört alone, so of course the city has a strong fine-wine scene as well. Wine Spectator reached out to six leading Chi-town sommeliers for the places they go for a great glass of wine, including in greater Chicagoland. (And don’t miss the contributing somms’ wine programs, which have all won Wine Spectator Restaurant Awards!) “Chicago is such a great wine-drinking city,” Alex Cuper, wine director of Award of Excellence winners El Che and Brasero told us. “There are so many awesome yet unpretentious places around the city that can offer so many different experiences when it comes to enjoying wine!”
12 of the Top Wine Bars and Restaurants in Chicago
- Webster’s Wine Bar
- Easy Does It
- Daisies
- Bar Parisette
- Osteria Langhe
- Le Midi Wine
- Brasero
- Tuman’s Tap and Grill
- Maxwells Trading
- Rootstock Wine and Beer Bar
- Montage Wine Bar
- Wine and Cheese
Logan Square and Palmer Square
Webster's Wine Bar
“[Webster’s Wine Bar] is forever and always my standby. No matter who is there, there is always a wealth of wine knowledge to be passed along. I love to swing by on Mondays and participate in their blind tasting where they randomly choose three bottles, bag them and give you a flight to taste and submit answers to win a gift certificate. If that isn’t your jam, just hanging out at the bar and working your way through many glass pours is always fantastic too!”—Alex Cuper, beverage director of Award of Excellence winners El Che Steakhouse & Bar and Brasero
Easy Does It
“I really enjoy Easy Does It. There are always exciting by-the-glass offerings, the list is affordable, and I usually end up talking to someone at the bar I didn’t know before I arrived. Zack Eastman has done an excellent job curating the list, building an inviting space with knowledgeable staff, and marketing events like collaboration tastings with other wine bars and pop-ups for food vendors who don’t have a brick-and-mortar yet that make you want to call off of work to be there. It sets a high bar for what a neighborhood wine bar can be.”—Jake Bennie, wine director at Award of Excellence winner Rose Mary
“[At Easy Does It], formerly the East Room, Zack Eastman is doing some awesome stuff with a huge focus on the natural wine world. It’s a great space with an incredible ever-rotating glass pour list and DJs frequently. Along with the bottle shop in the front, they also frequently host really great tastings. Overall, an easy (wink wink), comfortable place to try some cool stuff!”—Alex Cuper
Daisies
“I love that the wine list [at Daisies] shares their spirit of Midwest ingredients through Italian cooking. The fact that there’s so many Midwestern wines, and good ones at that, makes me want to skip right over the impressive Italian selections.”—Scott Stroemer, beverage director of Award of Excellence winner Galit
Bar Parisette
“I drink at other wine bars and bars, with or without my two-and-a-half-year-old, two dogs and my wife (when she is not working). We actually just went to Bar Parisette. It’s a relatively new joint in town. Great wine list, mostly French, mostly natural with a couple of skin-contact options. Really pretty. It reminds me a bit of Frenchette in New York City.” —Eduard Seitan, partner and wine director Award of Excellence winner avec
Osteria Langhe
“I love Italian wine, and I love wine lists with a distinct perspective. [Award of Excellence winner] Osteria Langhe hits both of those things for me with the added bonus of maybe my favorite plate of food—the plin ravioli—in the whole city of Chicago. Osteria Langhe focuses on specifically Northern Italy both in wine and cuisine. It is truly one of my favorite neighborhood restaurants and arguably the best Italian restaurant in the city.”—Alex Cuper
“Since Soif closed [in 2022], I have been paying homage to Aldo Zaninotto [its owner] by going to his other spot, Osteria Langhe. This is where you go granular. The wine list is all Piedmontese, Langhe-focused. Great spot for an amazing glass of Nebbiolo. And much more. I have known and loved Aldo for about 25 years.”—Eduard Seitan
Wicker Park
Le Midi Wine
“Le Midi Wine is two blocks away from my house—convenient, eh?—and has a beautiful patio, very dog-friendly. Really cool, international list from the brain of Craig Perman, one of the best palates in the city.”—Eduard Seitan
West Town
Brasero
“A hundred wines under a hundred bucks is a great hook, but the real meat of the wine list [at Award of Excellence winner Brasero] is the fact that all 100 are South American without excuses or apologies. I greatly respect how Alex and chef John Manion lean so hard into it. The staff has the knowledge to make it work, to guide guests to a world of wines that’s unfamiliar and amazing.”—Scott Stroemer
Ukranian Village
Tuman’s Tap and Grill
“This neighborhood bar in the Ukrainian Village has amazing bar food, a hefty seasonal beer selection, and quality wine that is sold at a more-than-reasonable markup.”—Kathleen Hawkins, wine director of 2024 Best of Award of Excellence winner, Tre Dita, and 2024 Award of Excellence winner, Miru
West Loop
Maxwells Trading
“I worked with chef Erling Wu-Bower for many years and, when he told me that he was handling the wine list [at Maxwells Trading] and would be on the floor for service, I knew it would be fun. I mean, who better to suggest wines than the chef who selected them? It’s a cool list that, much like the food, takes what made Nico and Pacific Standard Time special and fuses them with all of Erling’s other influences and presents them without needing to overthink itself into labels.”—Scott Stroemer
Humboldt Park
Rootstock Wine and Beer Bar
“Rootstock is a beloved wine bar with an extensive list in a low-key setting. The seasonal food menu changes often but is always tasty, and they serve one of the best burgers in the city.”—Kathleen Hawkins
Greater Chicagoland
Montage Wine Bar
“Located just outside of Chicago, one of my go-to spots to just chill, relax and enjoy the ambiance is Montage Wine Bar in Morris, Ill. This wine bar is super cozy and I’m always greeted with a warm smile from the staff there, which includes the owner, Michelle Xydakis, herself. Montage offers a world-class wine list, from all over the world, in addition to small plates and charcuterie boards to pair with my perfect glass of vino. Live music seals the deal as I’m transported to the coast of Italy, Spain, Greece, Oregon and beyond. No matter what the occasion or what kind of day I’m having, Montage always makes it better!”—Marsha Wright, wine director of 2024 Award of Excellence winner LYRA
Wine and Cheese Co.
”Nestled in the heart of downtown Plainfield, Ill., Wine and Cheese Co. is a gem serving up wine bottles from across the globe, with a lively atmosphere and superb staff. I always discover something new with each visit! Owner Kacie Hollenbeck supports local artisans with custom artisanal charcuterie and a small-bite menu that makes my soul sing with joy.”—Marsha Wright
