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Fun Activities with Wine

You want to stay active while enjoying a glass of wine, because the two don't have to be mutually exclusive.

Based on 788 Opinions
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Updated May 2026
01
Above Average DIY Candle Studio image 1
Above Average DIY Candle Studio image 2
Above Average DIY Candle Studio image 3
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Small, intimate studio in a basement offers DIY candle making paired with wine tasting and chocolate. Warm, welcoming atmosphere filled with great music and a friendly, energetic vibe encourages connection and fun among couples and friends.

Mixing hot wax that glows in the dark creates a relaxing and interactive experience. Classes like the lovers candle session offer a fun and sweet activity hosted by a warm and engaging instructor.

Wine pairs with chocolate in a couples tasting that includes refreshments and birthday cupcakes. Workshops combine wine tasting with candle making led by Kurt and Marz.

People are saying

"Karen made the whole experience so fun and lively."

"It's a fun, unique experience for a creative date night."

"Sam made the candle-making experience so fun and exciting."

Good to know

1

Reservations are recommended for all events to ensure availability.

2

Candle-making classes are available for couples and groups, providing a fun interactive experience.

3

Murder mystery events are popular and provide a fun twist to the candle-making class.

02
Augusta Food and Wine image 1

Tiny shop with carefully curated wines and cheeses creates a welcoming neighborhood vibe without snobbery. Handwritten notes on bottles and a unique monthly wine club offer discovery and expertise. Reasonable prices and specialty foods make it accessible and inviting.

Great value on wine and spirits adds to the fun. Cheese selections and gourmet goodies offer tasty options to enjoy.

Selection includes unique wines from around the world with many bottles under $20. Staff offers knowledgeable recommendations and hosts free Thursday night tastings to explore new options.

People are saying

"The staff here are super knowledgeable about wine and give great recommendations."

"I found amazing, cool, and unique wines because it's so well-curated."

"The staff here are super helpful and knowledgeable."

Good to know

1

Free wine tastings are held every Thursday evening.

2

The wine club features unique selections from small vineyards each month.

3

Expect a friendly atmosphere with knowledgeable staff ready to help.

03
Grand Cru Chicago image 1

Large, inviting space offers a laid-back atmosphere with a diverse global wine selection. Regulars and newcomers mingle in a cozy, unpretentious setting that feels like a community hangout. Unique, niche wines from less common regions create an exploratory tasting experience.

Wine tastings focus on themed regions like Willamette Valley, Sicily, and Bordeaux, combining education with fun. The lounge offers a sexy, unpretentious vibe that suits events like birthday parties and food pairings.

Thoughtful wine tastings focus on regions like Willamette Valley and Sicily, offering a fun and educational experience. The owner curates an incredible selection from countries such as Greece, Argentina, and South Africa, providing unique varietals hard to find elsewhere.

People are saying

"Matt curated a personal wine flight with unique, niche selections."

"You'll discover unique wines you won't find elsewhere."

"The owner curated great wine selections and offered tailored tastings."

Good to know

1

Comedy Cru events happen regularly, offering a fun night out with laughter.

2

Wine tastings feature themes like Willamette Valley and Bordeaux, providing educational experiences.

3

Happy hour tastings are available, showcasing a solid selection of wines.

04
Class Act image 1
Restaurant

Communal table seats up to 16 with an open kitchen where chefs prepare inventive dishes inspired by personal stories. Atmosphere blends elegant warmth with a close-knit, family dinner vibe, encouraging conversation among diners. Attached speakeasy offers advanced mixology for a refined post-dinner experience.

A unique progression shapes the night with a cool communal table that makes the experience very interactive and fun.

Champagne pairing includes both still and sparkling wines with detailed descriptions from the sommelier. Staff focus on knowledgeable wine pairings and unique selections from around the world complement each dish.

People are saying

"The cocktails here are inventive and paired phenomenally with the dishes."

"The tasting menu was inventive and unforgettable."

"The wine staff are so knowledgeable and attentive."

Good to know

1

Reservations are required due to limited seating, with only 12 guests per seating.

2

The tasting menu is fixed with no pre-check available for dishes.

3

Expect the dining experience to last a couple of hours with multiple courses.

05
Italian Homemade Company image 1
Italian restaurant

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.

Pasta making classes led by Alberto offer a fun experience with an instructor who keeps things engaging and approachable.

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.

People are saying

"The homemade pasta here is delicious and fresh."

"I learned to make amazing pasta from scratch in a fun, hands-on class."

"I enjoyed a bottle of wine with my pasta."

Good to know

1

Happy hour runs from 3 to 6 pm, Monday through Friday.

2

Pasta 101 class teaches how to make authentic pasta.

3

Happy hour features $7 cocktails and espresso martinis.

06
Birch Road (Lincoln Park) image 1

Social club offers a cozy, private space with temperature-controlled wine lockers and mini clubs for activities. Atmosphere stays warm and inviting, encouraging mingling and relaxed socializing. Community feels inclusive, blending casual comfort with stylish design.

Events include wine tastings and various clubs that create a casual, social vibe. The space supports cocktail making and easy mingling in a relaxed setting.

Wine events offer tastings and educational experiences with a focus on discovering new varieties. Temperature-controlled lockers provide secure storage for special bottles, supporting a community passionate about wine and culture.

People are saying

"I loved the wine and the cosmopolitan people here."

"The staff made the party easy and fun."

"The crew here makes it so easy and fun."

Good to know

1

Wine tastings and cocktail-making classes are popular events held regularly.

2

Birch Road is BYOB, allowing guests to bring their own drinks.

3

The venue is suitable for private events and gatherings for up to 60 people.

07
Wild Blossom Meadery and Winery image 1

Outdoor space includes a flower garden, backyard patio, and fire pit area with gazebo seating for shade. Atmosphere feels like an oasis, peaceful and inviting with good music and lively vibes. Offers both indoor and outdoor dining with a game room for kids and a focus on sustainability.

Tasting and tours offer a fun and informative experience with tasty, fruity sweet mead. The garden provides a relaxing spot to hang out and enjoy drinks in the sun.

House-made wines offer a wide variety of delicious options. The selection includes both wine and meads, paired well with cheese and crackers.

People are saying

"The staff here is so friendly and informative about the wine."

"The outdoor space here is a beautiful, peaceful oasis with a patio."

"I had a fun experience with the tasty, fruity mead."

Good to know

1

Bingo nights occur on certain evenings for a $10 entry fee.

2

Wild Blossom Meadery and Winery hosts wine-making events from a kit.

3

Reservations are recommended for special events to secure a spot.

08
Alhambra Palace Chicago image 1
Mediterranean restaurant

Dining hall showcases Moroccan art and waterfalls, creating a breathtaking and authentic atmosphere. Entertainment includes phenomenal shows and a DJ mixing for a multicultural crowd, adding lively energy. The vibe feels like a journey between Chicago and Morocco, blending historical touches with vibrant performances.

Crazy fun energy fills the space with a mix of dinner and a show that keeps things lively. Activities blend seamlessly with entertainment for a unique, engaging experience.

Lebanese wine stands out as a notable choice here, with staff like Huda and Amine offering professional and friendly help selecting bottles. Some wines taste watered down, so many opt for wine or beer to avoid disappointment.

People are saying

"The food here is delicious, with tender lamb shanks that melt in your mouth."

"The food here is so delicious and flavorful."

"I thought the Lebanese wine here was the best in Chicago."

Good to know

1

Salsa night happens every Thursday with dance lessons starting at 8pm.

2

A default gratuity of at least 18% is added to all bills.

3

Expect a cover charge for special events, typically around $10.

09
BottlesUp! image 1
Wine store

Open and inviting space encourages both conversation and independent browsing with an atmosphere that feels welcoming and non-pretentious. Regulars include wine and rum enthusiasts who appreciate the unique curated selection and affordable tastings. The shop stands out for its exceptional spirits collection and community-focused events that make it a neighborhood gathering spot.

Creative and well curated events happen regularly, including tastings that bring a fun vibe. Melissa, a community-focused person, adds to the lively atmosphere with her involvement.

Curated by Melissa, the selection features unique wines and non-alcoholic options. Staff provide helpful background and pairing advice, making it easy to find wines for any occasion.

People are saying

"The staff here is so knowledgeable about wine and helped me find a great bottle."

"The wine selections here are so interesting and tasty."

Good to know

1

BottlesUp hosts regular tastings and special events throughout the year.

2

Wine club memberships are available at BottlesUp, offering exclusive benefits.

3

Expect a welcoming atmosphere, perfect for both wine novices and enthusiasts.

10
Alexandra Marks image 1
Jewelry store

Jewelry store offers a warm, welcoming atmosphere with an energetic, fun vibe that suits groups or couples well. The space feels comfortable and friendly, encouraging easy conversation and a sense of familiarity. Visitors can enjoy complimentary sparkling wine while browsing a diverse selection of permanent jewelry.

Getting a permanent ring here is quick, painless, and genuinely fun. The team, especially Candy, makes the whole process memorable and enjoyable for everyone involved.

Complimentary wine greets guests upon arrival, often including rosรฉ. Free refills and helpful pours accompany purchases, creating a welcoming wine experience.

People are saying

"The staff at this jewelry store are so welcoming, patient, and helpful."

"Getting permanent jewelry here was a fun bonding experience."

"They offered us complimentary wine with the experience."

Good to know

1

Appointments are recommended to ensure priority over walk-ins.

2

The jewelry shop offers a wide variety of permanent bracelet options.

3

Prices for permanent bracelets range from $60 to $250.

11
GG Piano Bar Cocktail Lounge image 1

Dark, lively space with a 1930s distillery basement vibe and live piano music that fills the room loudly. Comfortable seating and an upscale speakeasy style create a cozy yet energetic atmosphere. The crowd gathers mainly on weekends, enjoying unique cocktails and interactive music experiences.

Performances feature singing and dancing, creating a lively atmosphere. A show with lighting strawberries and cigarettes adds a unique, interactive touch to the fun.

Happy hour offers $25 bottles of wine. The wine selection is great and very good. The spot feels swanky and gorgeous, pairing wine with live music and a solid whiskey, scotch, and bourbon lineup.

People are saying

"The bar staff here are attentive and friendly."

"The live piano music here makes for a really fun night out."

"The wine bar has a gorgeous, fun musical vibe."

Good to know

1

A $20 cover charge applies for live music nights.

2

An automatic gratuity of 21% is added to all bills.

3

Happy hour features $25 bottles of wine on Wednesdays.

12
The Comedy Clubhouse image 1

Small, intimate comedy club with a cozy atmosphere and laid-back vibe. Sharp, funny improv performances create an upbeat energy that encourages interaction between comics and audience. Features a self-serve beer wall offering local draft brews and ciders, adding a unique touch to the experience.

Lively atmosphere and engaging employees create a fun vibe for a night out. Suitable for groups, dates, or solo visits, it offers a consistently enjoyable experience.

Wines come by the bottle at reasonable prices. Options include self-serve beer and cider pours alongside canned cocktails.

People are saying

"The improv here is sharp, funny, and incredibly entertaining."

"I had a blast and experienced some of the most fun times here."

"The wine here is amazing and made us laugh."

Good to know

1

Tickets for shows are affordable, typically half the price of larger theaters.

2

The venue hosts three shows on Saturday nights starting at 6:30 pm.

3

Food and drinks are reasonably priced, with a pay-by-the-ounce craft beer tap.

13
No Vacancy image 1
Restaurant

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.

Watching games here feels lively with fun drinks and friendly bartenders who keep the energy up.

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

People are saying

"I found the birria egg rolls to be absolutely delicious."

"You've got to try the birria egg-rolls and sliders!"

"I was impressed by their random and dope wine selection."

Good to know

1

Happy hour runs from 4:30 to 6:30 pm with half-price appetizers and drinks.

2

Expect a lively atmosphere, especially during NFL games on weekends.

3

The menu features unique dishes but is small enough to not be overwhelming.

14
Rooftop Cinema Club Fulton Market image 1

Outdoor movie theater on a rooftop offers fantastic views and an elegant atmosphere with individual headphones that provide clear sound and block outside noise. Cushioned chairs and fun games create a relaxed, enjoyable vibe suited for date nights or casual outings.

Outdoor movie screenings create a unique atmosphere for a date night or group outing. The space includes fun games and an adorable setting that adds to the enjoyment.

Sparkling wine comes in small bottles priced around $20, enough for one person. Wine is sometimes served at room temperature, which may not suit all tastes.

People are saying

"The rooftop movie experience here is awesome and unforgettable."

"I found the experience to be really fun and cool."

"I loved the great variety of wine choices available."

Good to know

1

Arrive early to secure good seats as there are no reserved spots.

2

Bring a blanket for chilly evenings, as they do not provide any.

3

Food and drink options are limited, with only one available during my visit.

15
EL RINCON DE FABIO LLC image 1
Venezuelan restaurant

Small space filled with beautiful Venezuelan decor and a cozy, family-friendly atmosphere. Latin music plays softly, creating an awesome vibe that feels welcoming and pleasant. Outdoor patio offers a nice option for seating in good weather.

Fun atmosphere shines with lively music and an engaging environment. Authentic dishes add to the overall delicious and enjoyable experience.

Free wine flows with meals, mostly red wine. The wine tastes delicious and pours endlessly during dining.

People are saying

"I found the pabellรณn arepa to be delicious."

"I loved the endless flowing free wine."

"The atmosphere here is so fun and the food is delicious."

Good to know

1

Free drinks are offered after 5pm every day.

2

Enjoy free margaritas daily after 2:00 PM.

3

Free wine is available on Fridays.

16
Tortoise Supper Club image 1
American restaurant

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.

Fun bar staff create a lively atmosphere. The spot suits both romantic dinners and nights out with friends.

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

People are saying

"The food at these dinner spots was spectacular and delicious."

"The wine knowledge here is wonderful and the servers are attentive."

"I loved the live jazz performances here."

Good to know

1

Reservations are required for private events and should be made well in advance.

2

Happy hour runs from 4-6pm on weekdays with discounted drinks and appetizers.

3

Valet parking costs $16 for three hours, making it convenient for guests.

17
Esmรฉ image 1
Restaurant

Dining space resembles an art gallery with rotating exhibits integrated into plating and decor. Atmosphere stays comfortable and elegant, avoiding fine dining pretension while feeling welcoming and calm. Guests experience creative presentations alongside carefully crafted cocktails and dishes.

The experience offers genuine fun through both the meal and the service. It feels refreshing and justifies the cost with its engaging atmosphere.

Wines come beautifully matched with the tasting menu, enhancing each course. The avant-garde pairing mixes beers, wines, cocktails, and unique options for variety.

People are saying

"The cocktails here are unique, artfully presented, and inspired by the gallery."

"It's a fun activity to eat art and look at art here."

"The wine and service here felt so attentive and professional."

Good to know

1

Reservations are recommended, especially during busy dining hours.

2

The tasting menu changes every 12 weeks, inspired by a local artist.

3

Expect to pay around $80 per person during Chicago Restaurant Week.

18
Millennium Hall Restaurant image 1

Architecture features Frank Gehry's dancing metal design with indoor and outdoor seating offering views of the ice rink and cityscape. Atmosphere ranges from festive and chill to lively with large projection TVs showing sports. Popular for group outings and casual dining with a bar-focused vibe.

Chef David leads with knowledge and passion, making the pizza-making lesson both fun and approachable. The experience includes pizza, drinks, an appetizer, and clear instruction, creating a great group activity.

Red wine here is tasty and pairs well with events like DIY pizza making. The wine offers a lovely flavor that complements casual gatherings.

People are saying

"Chef David's pizza making class was so fun and awesome."

"Chef David made the pizza-making experience fun and unforgettable."

"I discovered this place during a fun pizza making wine event."

Good to know

1

Reservations are recommended for pizza-making courses and private events.

2

Happy hour runs from 4-6pm with discounted drinks and appetizers.

3

Karaoke night starts at 10pm on Thursdays with a two-drink minimum.

19
Le Piano image 1
Jazz club

Jazz club offers intimate candlelit setting with Chicago-style Parisian bistro decor and live experimental music performances. Atmosphere feels romantic and cozy, ideal for evening jazz and drinks. Seating layout and lighting create a refreshing vibe that highlights the music and ambiance.

Outdoor patio offers a charming fireplace and a space that feels lively and fun. Music sets an exemplary, upbeat tone that adds to the positive energy throughout the area.

People are saying

"The jazz here is soulful in an intimate, amazing atmosphere."

"The wine here creates such a warm and inviting atmosphere."

"The live jazz music here is fantastic and fun."

Good to know

1

There is a music fee of $15 per person for entry.

2

Live jazz is played on weekends until 1 am.

3

Brazilian Jazz performances occur on Wednesdays.

20
CloudBar at 360 CHICAGO image 1

Bar atop a skyscraper offers 360-degree city views and a rooftop lounge with ample seating. Atmosphere shifts from relaxed during sunset to lively as night falls, with a mix of tourists and locals. Entry requires a ticket, and the setting includes unique attractions like a thrilling tilt experience.

Fun activities include a thrilling tilt experience that changes the view and the Cloud Bar offers options for all ages. The Cloud margarita adds a playful touch to the menu.

Offers house can sav and a bottle of Blue Moon. Wine costs about 16 USD for 100 milliliters. Views include the whole city while sipping.

People are saying

"The city views from here are amazing and totally unbeatable."

"The panoramic views of the city and lake are breathtaking."

"I enjoyed seeing the whole city with a glass of wine."

Good to know

1

Entry to the bar requires a general admission ticket costing around $40.

2

Expect a 30-60 minute wait for seating during peak hours.

3

Drinks take about 15 minutes to arrive after ordering.

21
Little Victories image 1

Mid-century modern bar with moody lighting and an indoor/outdoor setup creates a lively yet welcoming atmosphere. Games like pool and darts occupy half the space, encouraging casual fun. The U-shaped bar serves exceptionally good cocktails, including standout espresso martinis.

Pool table and darts board provide fun ways to pass time. The space feels lively and offers a good spot to hang out with friends.

White wine offers a fruity aroma and taste. Half-price bottles on Sundays make wine more accessible. Proper wine glasses would improve the experience.

People are saying

"The bar's cocktails are creative and well-made."

"They have fun activities like pool and darts."

"I enjoyed the wine and the Caesar wraps."

Good to know

1

Happy hour runs all day with a few discounted drinks available.

2

Half-price bottles of wine are offered on Sundays.

3

ID is required for entry, even for food orders.

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