Wine and happy hour in Chicago

Wine bar offers a huge wine selection and a chill, laid-back atmosphere with a tucked-away patio perfect for relaxing. The pace is slow, encouraging guests to savor meals like charcuterie and oysters alongside their drinks. The space feels like a surprising little hideaway away from city bustle.

Offers a huge wine selection with flights available for tasting. Staff provide helpful recommendations and pair wines well with charcuterie and appetizers.

Happy hour offers half-off glasses, making drinks about $5-7 each. No corkage fees apply on full bottles, and they serve free duck fat popcorn during this time.

Speak-easy bar with dim lighting and comfortable lounge seating creates an intimate, cozy atmosphere ideal for quiet conversation. Upstairs event space offers a mingle-friendly setup with leather couches and high-top tables. Outdoor patio is dog friendly and opens to the sidewalk, blending indoor and street vibes.

Offers an amazing and diverse wine selection with reasonable prices. Servers suggest wines that pair well with food, and the spot stays open late for relaxed wine nights.

Happy hour offers a lowkey sexy vibe with a cute setting. It works well for both casual drinks and hosting events.

Cozy blend of industrial and mid-century modern speakeasy styles with exposed brick, murals, and velvety colors creates a romantic, intimate atmosphere. Soft classic salsa and bachata music sets a warm, inviting vibe. Creative space design and curated cocktail offerings distinguish it from typical steakhouses.

Unique wines from Mexico stand out here. Two bottles, including Flor de Canela, pair perfectly with meals and offer excellent flavor.

Historic building hosts a French bistro with European charm and elegant design. Live jazz music creates a relaxing atmosphere complemented by a skilled bar offering standout cocktails. The space feels cozy and stylish, attracting those seeking a refined dining experience.

A great wine list offers both high quality bottles and affordable options. Staff provide knowledgeable pairing advice, serving wines at the perfect temperature to complement meals.

Happy hour runs from 2 to 5 pm with a thoughtfully curated wine list and French classics like French Onion Soup. Bar seating offers sliders and fries alongside drinks.

Steakhouse offers a stylish and warm dining room with quiet sophistication and a relaxed but upmarket atmosphere. Cocktails are expertly crafted, complementing the coal-cooked steaks that define the menu. Private rooms and a dynamic space support both intimate and business gatherings.

An extensive wine list offers a wide range of choices. Sommeliers provide helpful pairing advice and recommend bottles that complement meals well.

Offers amazing deals on steak, burgers, and oysters during happy hour. The menu includes a gourmet Big Mac and good oysters that stand out.

Small brasserie with mid-century modern decor offers a cozy, relaxed atmosphere without loud music. Guests enjoy creative cocktails and highly praised burgers and pasta. Open window booths provide a gentle breeze and views of nearby ice skating.

An awesome wine list offers a variety of options. Waitstaff recommend wines that often turn out fantastic. The overall selection stays decent and approachable.

Happy hour offers surprisingly good value with specials that stand out. Mordecai features a great happy hour that draws attention.

Spacious, clean interior with an open kitchen creates a transparent and inviting setting. Atmosphere stays relaxed and enveloping, with Italian new songs adding to the vibe. Pasta dishes stand out as exceptionally delicious, paired well with a selection of Italian wines and cocktails.

An appropriate selection of wines pairs well with homemade pastas and sandwiches. The spot also offers house cocktails and beer, making it easy to grab a bottle and enjoy a relaxed vibe.

Happy hour runs from 3 to 6 pm on weekdays with $7 cocktails and great espresso martinis. It offers a solid value for drinks during that time.

Small space with cozy, friendly vibe and bright, warm decor creates a welcoming atmosphere. Loud with simultaneous conversations and music, it feels lively and fun. Offers carefully curated wine selection and artisan foods in an intimate setting.

Staff offer advice on unique natural wines that pair well with meals. The selection includes approachable wines by the glass and a funky orange wine for adventurous palates.

Great deals come from the happy hour menu with delicious wine and snacks. The happy hour rules are clearly posted and easy to follow, starting at 2:00 pm with orders accepted promptly after.

Dark academia decor creates a classy yet casual vibe with comfortable bar seating and large screen TVs for watching games. The atmosphere stays fun and welcoming, featuring DJs on weekends and a solid beer tap system. Food and drinks include amazing birria egg rolls and craft cocktails, making it a popular spot for game days.

Offers a random and dope selection of high-end wines by the half or full glass. Wednesdays attract wine enthusiasts for the varied choices.

Happy hour offers half price food and drinks with solid deals on appetizers and beverages. The menu features amazing food and drinks at a discounted price, making it a popular time to visit.

Hidden patio with heated cabanas creates a cozy atmosphere ideal for relaxed evenings. The space draws a crowd seeking intimate outdoor seating and a calm vibe. Wine flights and French onion soup stand out as notable offerings.

A vast selection of wines stands out, accessible via a menu QR code. Draft wines and a $9 per pour special for red and white wines add variety. Service includes knowledgeable recommendations that often lead to ordering multiple bottles.

Happy hour features $1 oysters and $7 Spritzes. Drinks and a charcuterie menu are available on the back patio.

Restaurant occupies an elegant second-floor space with amazing views of Michigan Avenue. Atmosphere feels funky and cool yet allows easy conversation without yelling. Offers masterfully made exotic cocktails and a lively bar with sports TVs.

Napa Valley red wine pairs well with steak here. The bartender and sommelier offer wine recommendations and let you sample before choosing. The wine selection complements the dining experience.

Upscale vibes shape the happy hour with a great deal on cocktails that often outshine the menu. Weekday sessions bring a fun atmosphere for groups and intimate dinners alike.

Bright, stylish space offers front-row kitchen views and classy indoor and outdoor seating. Atmosphere shifts from relaxed up front to more refined in the back dining room, creating a welcoming vibe for drinks or meals. Cocktails stand out with creative, well-crafted options like Negroni and martinis.

Healthy pour wine pairings complement each bite and highlight the ingredients. The wine enhances dishes like crispy potato with sturgeon caviar, balancing starchy and salty flavors.

Offers a cheap happy hour with a solid cocktail selection and a good menu. The happy hour experience feels next level and fantastic.

Modern steakhouse with sleek black decor and comfortable seating creates a friendly yet elegant atmosphere. The vibe balances casual and sophisticated, welcoming guests in casual clothes. Excellent margaritas and steaks complement the stylish setting.

An extensive and well-curated wine list offers options to pair with every dish. Staff provide attentive service and guide with great food and wine pairing, highlighting underrated Mexican wines.

Happy hour features $10 margaritas and three tacos for $10, making it easy to enjoy drinks and bites without spending much. Unique appetizers offer enough variety to make a meal out of the deals.

Outdoor patio offers a warm, intimate atmosphere with live music and comfortable seating. Interior design feels classy and elegant, creating a friendly, welcoming vibe ideal for relaxed evenings or social gatherings.

An impressive wine selection features great wines by the glass, including a notable Greek red. Wine pairings complement the chef’s tasting menu well, enhancing the overall experience.

Happy hour features buy one get one free drinks and inexpensive $5 appetizers. The patio offers a nice spot to enjoy a great selection of wines by the glass and small bites.

Sleek and modern wine bar offers a wide selection of champagnes and unique bottle service. Atmosphere feels sophisticated and upscale but somewhat sterile rather than cozy. Comfortable seating with ice buckets at window tables encourages conversation and people watching.

Offers a wide selection of sparkling wines from Champagne, Prosecco, Cava, and beyond. Features wine and cocktail menus with options by the glass and bottle, including beautifully crafted cocktails.

Happy hour runs until 6 pm with many options for after work drinks. Sparkling champagne and a $12.00 Sparkling Rose stand out as affordable bubbly choices.

Small sandwich shop with an integrated cozy bar offers a laid-back vibe and warm, inviting atmosphere. Known for house-made sourdough bread and elevated sandwich fare, it attracts those seeking quality ingredients and quick service at economical prices.

Fun wines come from a decorated sommelier, with options available during a lively happy hour. Countertop seats invite enjoying a glass of unique wine alongside charcuterie or takeout picnic orders.

Happy hour features a wonderful selection of wines that stand out after work. The overall vibe during happy hour is worth a visit with a killer drink lineup.

Cozy space with Hollywood regency decor and mood lighting creates a speakeasy vibe. Bartenders craft exceptional cocktails, including standout Old Fashioneds and martinis. Atmosphere suits jazzy date nights and sophisticated dining with white tablecloths.

Wine pairing enhances the food noticeably. Requests for wines not on the menu get prompt delivery. Both cocktails and wine show careful selection and quality.

Modern steakhouse blends trendy club vibe with live DJ sets and bold neon decor. Atmosphere feels lively and energetic, with music often loud enough to dominate conversations. Cocktails stand out as fresh and flavorful highlights amid the setting.

Staff offer knowledgeable wine recommendations tailored to dishes like lamb. The wine list is great and wines are served in crystal glasses for a refined experience.

Happy hour features delicious food with highlights like steak frites. The overall experience is great and enjoyable.

Modern cafe with comfortable booths and ample seating, including outdoor space overlooking a dog park. Atmosphere blends trendy and cozy vibes, ideal for remote work and quiet weekday visits. Regulars enjoy great coffee and wine, with a lively yet relaxed energy.

A wide selection of wine offerings complements the coffee and cocktail menu. The wine quality is consistently great, supported by high quality customer service.

Offers a great happy hour with refreshing, cold drinks served by friendly staff. The spot has a super cute vibe and a good late night menu for after work.

Mediterranean restaurant with a rooftop bar offering spectacular city views and multiple seating options including fire pits and private couches. Live music creates a lively atmosphere that balances well with conversation. Cocktails and food receive strong praise, contributing to an overall vibrant and welcoming vibe.

Staff offer warm-hearted welcomes and thoughtful wine tastings to match food perfectly. Bartenders ensure satisfaction with carefully selected red wines.

Happy hour runs daily from 5 to 7 pm with a rooftop setting. The menu offers great drinks and food, and staff provide helpful recommendations.

Rooftop dining with a retractable roof offers a quaint and intimate setting complemented by large open windows that blend indoor and outdoor spaces. Atmosphere balances comfortable space and lively energy, though noise can rise during busy times. The setup supports group gatherings while maintaining a pleasant view and inviting vibe.

Selection includes well curated cocktails and wines but the wine list is sparse with few bottles and mostly expensive options. Wine quality is generally good but limited in variety.

Happy hour runs from 4-6pm with $3 off pizzas and discounted beer. The deals make it easy to start with drinks and snacks before dinner.

Steakhouse offers a sophisticated, relaxing atmosphere with warm lighting, wood, and leather creating a classic, comfortable space. Music stays at a conversation-friendly volume, supporting a peaceful, romantic vibe. Guests enjoy high-quality steaks and well-crafted cocktails in a setting that balances elegance with approachability.

Offers a nice wine selection with a good choice of options at reasonable prices. The wine pairs well with dishes like lamb chops and scallops.

Happy hour features cocktail specials that work well as a pre-show drink. The atmosphere suits a quick, enjoyable stop before dinner.

Seafood restaurant with quiet, elegant atmosphere and beautiful interior design featuring boat decor and funky wall art. Seating is comfortable and the space offers a small patio alongside plenty of indoor tables. The vibe suits a fancy dining experience rather than a casual, lively spot.

Offers a wonderful selection of wines alongside beers and a full bar. Wine pairs well with oysters and salmon, enhancing the flavors.

Happy hour features great deals on oysters and a varied menu including house roll, Kenai roll, and shrimp po’boy. It runs daily from 4 PM to 6 PM and offers a solid taste testing experience with snacks and drinks.

Italian restaurant offers a modern jazz inspired design with upstairs loft featuring live music and pool table. Atmosphere shifts from quiet and intimate dining to a lively late-night hangout with DJs and bands. Decor includes quirky records and stylish interiors creating a warm, upbeat vibe.

Knowledgeable servers recommend perfect wine pairings that complement flavorful dishes like tortellini and salmon toast. The wine selection includes reasonable bottles of white wine enjoyed during happy hour and brunch.

Happy hour features a fabulous menu with well-paired wine options. Service at the bar is attentive, making it a great spot for a relaxed Saturday evening.

Open, light-filled space blends stylish decor with Aussie sunshine vibe and welcoming neighborhood feel. Bar area features a massive TV and offers knowledgeable cocktail service with unique drinks. Indoor and outdoor seating create a relaxed atmosphere suited for casual meals and socializing.

The wine list features 100% Australian wines with a variety of styles for different palates. The extensive wines by the glass selection includes typical and tasty options, paired well with charcuterie and other dishes.

Happy hour features complimentary oysters and a special menu with solid deals. Cocktails like the Chapel-tini and Girl Dinner come from this menu.

Hotel offers cozy rooms with great city views and a quiet atmosphere despite occasional street noise. Lobby features a pleasant coffee bar and complimentary wine during happy hour. Valet parking next door and amenities like a small refrigerator and garment steamer add convenience.

A free wine hour runs from 5 to 6 pm with a comfy reception. Staff often offer a glass of wine even outside happy hour, including at check-in and when the lobby bar is closed.

Lively lobby hosts a free happy hour daily with complimentary wine and beer. Snacks like popcorn appear during some sessions, creating a relaxed vibe with quiet games and work areas nearby.

Elegant supper club blends live jazz music with a cozy, lively atmosphere featuring dark wood and colorful jazz-inspired wallpaper. Dining spaces include a private room with a bar, creating intimate vibes amid a bustling crowd. The setting combines elements of a jazz club and restaurant for a unique experience.

Friday happy hour features half off wine and $1 big oysters and shrimp. Staff offers great wine recommendations that enhance the experience.

Happy hour features $1 oysters and shrimp cocktail on Wednesdays and Fridays, with half off cocktails and wine. The oyster deal stands out as a rare find since the pandemic.

Spacious restaurant with modern, elegant decor and airy layout that avoids crowding. Atmosphere feels casual but chic, with loud music creating an energetic vibe. Tables require personal light to read menus due to dim lighting.

Generous wine pours include a Barbera Italian red. The wine pairs well with long nights of gossip and conversation.

Strong happy hour menu offers unique cocktails and $2 oysters at very reasonable prices. Great deals make it a solid choice for weekly visits.

Rooftop restaurant offers stunning city views and a relaxed atmosphere with friendly staff. The space features beautiful ambiance suitable for quiet meals or lively happy hours. Cocktails and small plates complement the setting, creating a charming dining experience.

The wine selection offers a great variety that pairs well with meals. The wine list is solid but not extensive.

Rooftop offers a fun happy hour vibe with drinks and food from 3:30 to 5:30 on weekdays. Food prices stay great value while drinks can be less impressive at this Spanish small plates spot.