Best Chicago Wine Shops For Gifting & Sipping

There’s no better way to spend the winter months than wrapped up in a blanket, listening to the crackling of a fireplace, with a good glass of wine in hand. And with the holidays coming up fast, everyone could probably use a drink. So, whether you're focused more on gifting or sipping, we’ve compiled a list of some of the best wine shops in the city that you just have to visit.

BottlesUp! {3164 North Broadway, Chicago; 773.362.4999}

Located in the charming Lakeview East, BottlesUp focuses on community and really good wine. The wine shop, opened in 2019, offers an array of beverages like wine, beer, spirits, sake, and even hard cider/kombucha/seltzers. Different from other shops, BottlesUp is organized by color to indicate the weight, or body, of the wine. This fun display is their unique way of categorizing types of wine and encourages people to try new things. Come one, come all, but don’t leave without a bottle!

Picnic Wine & Provisions {7301 North Sheridan Road, Chicago; 773.856.000}

If you want to feel like you have escaped the city and are in a small town spot away from all the noise, head to Picnic Wine & Provisions. Just twenty minutes north of downtown in the Rogers Park neighborhood, this diamond in the rough offers wine tastings every Thursday night on their patio filled with lights. While you’re there, check out their local bakery items and wine of the week. 

Perman Wine

Perman Wine Selections {1167 North Howe Street, Chicago; 312.255.8990}

Perman Wine, located in the Near North neighborhood, has great service, fair prices, and is no nonsense. With hand-picked wines, there’s no doubt you're getting the best the industry has to offer. You go to tastings, get individual wine delivered right to your door, and more, all from Perman. So if you need a last minute gift for your best friend's promotion she just got, or just want to stay in on a Friday night, they’re ready to do most of the work for you. 

City Winery Chicago {1200 West Randolph Street, Chicago; 312.733.9463}

Live music, award winning wine, and amazing views… What more could you want? With music on an almost weekly basis, the most delicious Lemon Curd Tartlet you can imagine and a wine flight to die for, you’d think you were in Napa Valley. Don’t forget to sign up for their wine club to get exclusive offers like monthly wine flights, private winery tours and more!

Webster's Wine Bar {2601 North Milwaukee Avenue, Chicago; 773.292.9463}

Known for their devotion to having an extensive list of natural wine, Webster’s Wine is definitely a hidden gem. If you want a solid place to bring a friend who is visiting for the holidays or a nice spot to unwind from the week, Webster’s is the place to be. Head to this nearly 30-year-old Logan Square spot for dinner and try their François Cazin vintage. With hints of bruised apple, pear, with savory notes of tarragon, lemon grass, and clove, you’ll think you were in the Loire Valley. 

Verve Wine Chicago

Verve Wine + Provisions {Lincoln Common, 2349 North Lincoln Avenue, Chicago; 773.904.8536}

Named after Verve Magazine, the French publication that introduced some of the most prominent artists of the Parisian art scene of the first half of the 20th century, Verve Wine and Provision embodies the same inspiring and creative ideals. Whether you want the newest and most exclusive wine, or need to fill holes in your collection that you can’t find anywhere else, Verve has you covered. Head to their Lincoln Park location and get a bottle that will impress even the most knowledgeable wine connoisseur.  

Black & Caspian Mediterranean Wine Bistro {2908 North Broadway, Chicago; 773.997.4461}

Located on bustling Broadway, Black & Caspian is a neighborhood favorite for many. Offering a wide array of wines and authentic modern Mediterranean dishes, your mouth will water just looking at the menu. It consists of wines and bites like Kabobs and Olive Tapenade that pay homage to the owners’ origins, near the Black and Caspian Seas (hence the name). Not only are the food and drinks great, but the service and atmosphere are warm and inviting.

Red & White Wines {1861 North Milwaukee Avenue, Chicago; 773.486.4769}

If you’re a newbie to the natural wine world and don't want to break the bank for a bottle of something without learning more, head over to Red & White. This Bucktown shop has a wide array of wines to choose from with a variety of price ranges, so there is something for everyone. Not only is the selection great, but customers rave about the knowledge of the workers in helping them choose the best wine for the occasion. Dip your toes into the world of wine at Red & White. 

By Madison Freeman | Special Coorespondent