Fine Dining at A Tavola

For a romantic evening out, consider booking a table at A Tavola. This upscale Italian restaurant offers a cozy ambiance and delicious cuisine that is sure to impress your date. Share a bottle of wine, indulge in some decadent pasta dishes, and enjoy the intimate atmosphere.

Alternative options: Pasta Fresca, Francesca’s Intimo, Tufano’s Vernon Park Tap

On-Demand Childcare in Your Neighborhood

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Wine Tasting at Glunz Family Winery & Cellars

Unwind and relax with your partner at Glunz Family Winery & Cellars. Take a tour of the vineyard, sample a variety of wines, and savor the flavors together. This experience is perfect for wine lovers looking to try something new and enjoy a leisurely evening.

Alternative options: City Winery Chicago, Lynfred Winery, Cooper’s Hawk Winery & Restaurants

Comedy Show at Zanies Comedy Club

Laugh the night away at Zanies Comedy Club. Enjoy a lineup of talented comedians as you sip on cocktails and share some laughs with your significant other. Comedy shows are a great way to lighten the mood and bond over a shared sense of humor.

Alternative options: The Second City, Laugh Factory Chicago, The Comedy Bar

Couples Massage at The Spa at KeyLime Cove

Indulge in a relaxing couples massage at The Spa at KeyLime Cove. Treat yourselves to a pampering experience that will help you both unwind and de-stress. Enjoy a tranquil environment and skilled massage therapists who will ensure you leave feeling rejuvenated.

Alternative options: Allyu Spa, The Peninsula Spa, Urban Oasis

Painting Class at Pinot’s Palette

Get creative with your partner at Pinot’s Palette. Sign up for a painting class where you can sip on wine and create a masterpiece together. This interactive and artsy date night idea is perfect for couples looking to try something new and showcase their artistic side.

Alternative options: Bottle & Bottega, The Painted Penguin, Arts n Spirits

Stroll Along the Lakefront Trail

Take a romantic stroll along the Lakefront Trail and enjoy stunning views of Lake Michigan. This scenic path offers a peaceful escape from the hustle and bustle of city life, allowing you to reconnect with nature and each other. Pack a picnic and watch the sunset for a truly memorable evening.

Alternative options: Millennium Park, Lincoln Park Zoo, Chicago Riverwalk

Concert at Ravinia Festival

Experience live music at the iconic Ravinia Festival. Grab some lawn chairs, blanket, and your favorite snacks as you enjoy a concert under the stars. From classical music to pop hits, there’s something for every music lover to enjoy at this outdoor venue.

Alternative options: The Chicago Theatre, Aragon Ballroom, House of Blues Chicago

Take a Cooking Class at The Chopping Block

Bond over a shared love of food by taking a cooking class at The Chopping Block. Learn new culinary skills, prepare a delicious meal together, and enjoy the fruits of your labor. Cooking classes are a fun and interactive way to spend quality time with your partner.

Alternative options: Sur La Table, The Wooden Spoon, The Social Table

Explore the Chicago Botanic Garden

Escape the city and immerse yourselves in the beauty of nature at the Chicago Botanic Garden. Wander through lush gardens, discover exotic plants, and enjoy peaceful moments together. Pack a picnic or enjoy a meal at one of the garden’s cafes for a relaxing day out.

Alternative options: Garfield Park Conservatory, Lurie Garden, Alfred Caldwell Lily Pool

Movie Night at New Vision Showplace 14

Spend a cozy evening at the movies at New Vision Showplace 14. Catch the latest blockbuster or opt for a classic film as you snuggle up with your partner. Share some popcorn, enjoy the big screen experience, and escape into a different world together.

Alternative options: Music Box Theatre, Arclight Cinemas, Arcada Theatre