Romantic Dinner at Lucrezia Ristorante

For a delicious and intimate dining experience, head to Lucrezia Ristorante. This cozy Italian restaurant offers a romantic atmosphere, perfect for a date night. Enjoy a glass of wine and savor the flavors of traditional Italian dishes while enjoying each other’s company.
Alternative options: Isabella Cafe, Tucci’s

On-Demand Childcare in Your Neighborhood

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Movie Night at AMC Showplace Calumet City 14

Catch the latest blockbuster movie at AMC Showplace Calumet City 14. Sit back, relax, and enjoy a film together in the comfort of a movie theater. Share some popcorn and enjoy a few hours of entertainment.
Alternative options: Marcus Orland Park Cinema, Emagine Frankfort

Wine Tasting at Cooper’s Hawk Winery & Restaurant

Indulge in a wine tasting experience at Cooper’s Hawk Winery & Restaurant. Sample a variety of wines and learn about the different flavors and notes. It’s a classy and enjoyable way to spend time together.
Alternative options: Lynfred Winery, Galena Cellars Vineyard & Winery

Bowling at Lan-Oak Lanes

Get your game on with a friendly bowling competition at Lan-Oak Lanes. Lace up your bowling shoes and hit the lanes for a fun-filled night of strikes and spares. Add some competitiveness to your date night!
Alternative options: Stardust Bowl, Orland Bowl

Painting Class at Bottle & Bottega

Get creative together with a painting class at Bottle & Bottega. Unleash your artistic side as you follow step-by-step instructions to create a masterpiece. It’s a fun and unique date night idea that will leave you with a lasting memory.
Alternative options: Pinot’s Palette, Arts N Spirits

Comedy Show at Riddles Comedy Club

Laugh the night away at a comedy show at Riddles Comedy Club. Enjoy a lineup of talented comedians that will have you in stitches. It’s a guaranteed good time that will bring you and your partner closer together.
Alternative options: Laugh Factory Chicago, Zanies Comedy Club

Live Music at J.J. Kelley’s

Enjoy live music at J.J. Kelley’s, a popular spot for local bands and musicians. Sip on cocktails, listen to great music, and dance the night away with your partner. It’s a lively and entertaining date night option.
Alternative options: Blue Chip Casino, The Venue at Horseshoe Casino

Escape Room Experience at Lock Chicago Escape Rooms

Put your teamwork skills to the test with an escape room experience at Lock Chicago Escape Rooms. Work together to solve puzzles and unravel the mystery before time runs out. It’s a thrilling and exciting way to bond with your partner.
Alternative options: Escape Artistry, Fox in a Box Chicago

Sunset Stroll at Burnham Park

Take a romantic stroll along Lake Michigan at Burnham Park. Watch the sunset together and enjoy the breathtaking views of the water. It’s a serene and peaceful way to spend quality time with your loved one.
Alternative options: Millennium Park, The 606

Couples Massage at Rejuvenation Med Spa

Pamper yourselves with a couples massage at Rejuvenation Med Spa. Relax and unwind as you both enjoy a soothing massage that will help you de-stress and rejuvenate. It’s the perfect way to end a romantic date night.
Alternative options: The Peninsula Spa, Allyu Spa

Before heading out for your date night, make sure to book a trusted sitter from Wyndy to take care of your children. With a reliable and experienced sitter in charge, you can enjoy your night out worry-free, knowing that your kids are in good hands.