Looking to unwind with a glass of wine in Chicago? From small-batch wineries to Champagne-focused bars, the city has a vibrant wine scene that caters to every palate. Here’s a guide to some of Chicago’s best wine spots to raise a glass and savor incredible selections.
Chicago Winery
Raise a Glass: Nestled in River North, Chicago Winery crafts its own small-batch wines in-house with grapes sourced from boutique vineyards. Stop by the bar for a tasting or elevate your evening with a meal at Liva, the on-site restaurant where wine pairings are designed to enhance every dish. The winery’s warm, welcoming atmosphere makes it a perfect spot for both casual sipping or a more refined dining experience.
Pull Back the Curtain: Want to learn more about how the wine is made? On weekends, take a 60-minute guided tour of the winery that includes five tastings. The tour offers an insider’s look at the winemaking process and provides the chance to sample a variety of wines while gaining a deeper appreciation of the craft. Whether you’re a seasoned wine enthusiast or a casual drinker, it’s a fun and educational way to spend an afternoon.
City Winery
Bottoms Up: Located in the West Loop, City Winery combines urban winemaking with a lively dining experience. Sip one of 13 house-made varietals while enjoying shared plates, wood-fired pizzas or a well-curated cheese and charcuterie board. The open and spacious setting is ideal for larger gatherings or an intimate evening out.
More Than Wine: In addition to its wine offerings, City Winery is also a hotspot for live entertainment. The back room hosts nightly performances from local and national musicians and comedians, making it the perfect venue to enjoy both wine and culture. Wine lovers can also take a behind-the-scenes tour of the winery every Saturday at three different time slots.
POPS for Champagne
Pop the Cork: For Champagne enthusiasts, POPS for Champagne in River North offers an unmatched experience. With over 200 sparkling wine and Champagne options on its list, POPS is a mix of casual fun and upscale indulgence. Whether you’re snacking on popcorn or savoring caviar, the atmosphere is both relaxed and refined. Happy hour here is a favorite, but you can also reserve a spot for their Saturday Tasting Series, which showcases unique Champagnes and sparkling wines from around the world.
Experience Counts: As the oldest Champagne bar in the U.S., POPS has been perfecting the art of sparkling wine since 1982. The long history and expertise shine through in every pour, making it a go-to destination for both Champagne aficionados and those new to bubbly.
Webster Wine Bar
Propose a Toast: Inspired by the wine bars of Seville, Webster Wine Bar in Logan Square takes pride in sourcing wines from family-run vineyards around the world. It focuses on wines made with minimal additives and chemicals, offering a pure, natural taste that wine lovers appreciate. The bar’s intimate setting makes it an ideal spot for a quiet night out with friends or a cozy date.
Distinguishing Feature: Webster’s menu stands out with its offering of Portuguese conservas—tinned fish served with sourdough, olives, and lemon. Pair these with one of their natural wines for a European-style experience right in Chicago.
Alpana
Expert Pairings: Founded by Master Sommelier Alpana Singh, this Gold Coast gem offers an exquisite blend of world-class dining and a stellar wine selection. The globe-spanning menu is crafted to complement the extensive wine list, which spans 24 pages. From classic Old World wines to new discoveries, Alpana delivers a refined yet approachable experience for wine lovers.
For the Curious: Every month, Alpana Singh highlights a different winery, offering a carefully curated tasting flight that’s perfect for anyone looking to expand their wine knowledge. The spotlighted wineries often feature rare or unique selections, making it an exciting experience for adventurous drinkers.
Apero Chicago
French Vibe on the North Side: Located in North Center, Apero Chicago offers a relaxed, French-inspired atmosphere where friends can gather for a glass of wine before dinner. The focus here is on biodynamic wines from small, independent wineries, with a standout selection of orange wines. Founder Robert Cervantes has created a space where the French tradition of apéritif comes to life, offering a casual yet stylish vibe.
Artisanal Approach: The menu at Apero changes seasonally, with both the food and beverages reflecting the freshest ingredients of the moment. Whether you’re enjoying a glass of orange wine or indulging in a seasonal small plate, the experience at Apero is always fresh and full of flavor.
