Fine Dining at The Cottage on Dixie

Enjoy a romantic dinner at The Cottage on Dixie, known for its cozy atmosphere and delicious American cuisine. This upscale restaurant offers a variety of dishes made with fresh, locally sourced ingredients. Indulge in a glass of wine and savor dishes like filet mignon or lobster tail while spending quality time with your significant other.

Alternative options: Lassen’s Tap, a charming gastropub with a rotating selection of craft beers and elevated pub fare, or Tilly’s Po’Boys, a casual eatery serving up New Orleans-style sandwiches and seafood dishes.

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Comedy Night at Riddles Comedy Club

Laugh the night away at Riddles Comedy Club, where you can catch a performance by top stand-up comedians. Sit back, relax, and enjoy a lineup of hilarious acts that are sure to keep you entertained throughout the evening. Share some laughs with your partner and make memories that will last a lifetime.

Alternative options: Laugh Factory Chicago, a renowned comedy club featuring local and nationally recognized comedians, or The Second City, a legendary improv theater with a rich history of producing top comedic talent.

Wine Tasting at Cooper’s Hawk Winery & Restaurant

Unwind with a wine tasting experience at Cooper’s Hawk Winery & Restaurant, known for its award-winning wines and upscale dining options. Sample a variety of wines paired with delicious small plates, and learn about the winemaking process from knowledgeable staff members. It’s the perfect way to enjoy a sophisticated evening with your loved one.

Alternative options: Lynfred Winery, a family-owned winery offering tastings and tours, or Water’s Edge Winery, a boutique winery specializing in handcrafted wines made from premium grapes.

Outdoor Movie Night at The Triangle Sports and Social Club

Cozy up under the stars and catch a movie at The Triangle Sports and Social Club’s outdoor movie night. Bring a blanket and some snacks, and enjoy a film in a relaxed and casual setting. It’s a fun and unique way to spend quality time together while enjoying the fresh air.

Alternative options: Millennium Park Summer Film Series, a free outdoor movie series in downtown Chicago, or Skyline Drive-In Theater, a classic drive-in theater with a retro vibe.

Painting Class at Pinot’s Palette

Get creative with your partner at a painting class at Pinot’s Palette, where you can channel your inner artist and create a beautiful masterpiece together. Enjoy a glass of wine as you follow step-by-step instructions from a professional artist, and take home a unique piece of art as a keepsake from your date night.

Alternative options: Bottle & Bottega, a wine and paint studio offering a variety of painting classes, or The Painted Penguin Art Studio, a cozy art studio with a focus on fun and creativity.

Live Music at Blue Island Beer Company

Immerse yourself in the vibrant music scene at Blue Island Beer Company, a local brewery and taproom that hosts live music performances. Sip on craft beers and enjoy the sounds of talented musicians while sharing a memorable night with your partner. It’s a great way to unwind and connect over a shared love of music.

Alternative options: 115 Bourbon Street, a popular entertainment complex with live music and a festive atmosphere, or The Quarry Event Center, a unique venue featuring live music events and private parties.

Couples Massage at Urban Wellness Chicago

Relax and unwind with a couples massage at Urban Wellness Chicago, a spa and wellness center dedicated to promoting relaxation and rejuvenation. Treat yourselves to a soothing massage that will help you de-stress and reconnect with your partner in a tranquil and peaceful environment.

Alternative options: Spa Space, a luxurious day spa offering a range of massage and skincare treatments, or Allyu Spa, an upscale spa with a focus on holistic wellness and relaxation.

Axe Throwing at Axe Marks the Spot

Get your adrenaline pumping with a thrilling axe-throwing session at Axe Marks the Spot, a unique indoor entertainment venue where you can test your skills and compete against each other in a friendly competition. It’s a fun and exciting way to bond with your partner and unleash your inner lumberjack.

Alternative options: Ragnarok Axe Throwing, another popular axe-throwing venue with multiple locations in the Chicago area, or Lumberjaxes Axe Throwing, a laid-back axe-throwing facility with a casual and welcoming atmosphere.

Brewery Tour at One Trick Pony Brewery

Embark on a brewery tour at One Trick Pony Brewery, a local craft brewery known for its innovative and flavorful beer offerings. Learn about the brewing process, sample different beer styles, and enjoy a behind-the-scenes look at the brewing industry. It’s a great way to experience something new and exciting together.

Alternative options: Hailstorm Brewing Co., a respected brewery with a diverse beer menu and a welcoming taproom, or Flossmoor Station Restaurant & Brewery, a historic brewery housed in a restored train station building.

Stroll Through the South Holland Farmer’s Market

Take a leisurely stroll through the South Holland Farmer’s Market, where you can browse a variety of local vendors selling fresh produce, artisanal goods, and handmade crafts. Sample delicious food offerings, pick up some unique gifts, and support local businesses while enjoying a relaxing and laid-back date night.

Alternative options: Homewood Farmers Market, a popular outdoor market with a wide selection of fresh produce and specialty foods, or Beverly Farmers Market, a community-focused market featuring local farmers and food producers.

When you’re ready for a night out away from your kids, consider using Wyndy to hire a trusted and vetted babysitter for the evening. Enjoy your date night in South Holland, IL with peace of mind knowing your children are in good hands.