• Le Colonial (Gold Coast): Celebrate in this charming French-Vietnamese restaurant with its lush, vintage-inspired decor and flavorful, exotic dishes.
• Mon Ami Gabi (Lincoln Park): Enjoy a classic French bistro experience with dishes like steak frites and escargot paired with fine wines.
• Piccolo Sogno (West Town): This romantic Italian eatery offers house-made pasta and an extensive wine list in a cozy setting, complete with a dreamy indoor patio.
  

Unique Events and Activities

• Valentine's Day "Dirty Dancing" Class: Duet Dance Studio offers a fun and interactive dance class inspired by the classic film, allowing couples to learn iconic moves together.
• Candlelight Concerts: Experience a romantic evening with classical music performances by candlelight at venues like Salvage One, featuring pieces from renowned composers.
• Eataly's Valentine's Day Festa: On February 13, indulge in a tasting event featuring over 10 stations and regional Italian wines, providing a delightful culinary journey.
  

Entertainment and Shows

• Taylor Tomlinson: The Save Me Tour: Enjoy a night of laughter with comedian Taylor Tomlinson performing at The Chicago Theatre on February 14 at 7:00 PM.
• Justin Timberlake - The Forget Tomorrow World Tour: Experience a memorable concert by Justin Timberlake at the United Center on February 14 at 7:30 PM.
  

Cruises and Scenic Views

• City Cruises Chicago: Choose from various Valentine's Day cruises, including the Premier Plus Dinner Cruise and Galentine's Brunch Cruise, offering dining with panoramic views of Lake Michigan and the city skyline
  

Creative Workshops

• Valentine's Day Pizza Cooking Class: Participate in a hands-on pizza-making session at Pizzeria Due, where you and your partner can craft your own delicious creations.
• LGBTQIA+ Single's Valentine's Day Candle-Making Workshop: Einnim hosts a candle-making workshop tailored for singles, providing a creative and inclusive environment to craft personalized candles.
  

Romantic Getaways

• Sophy Hotel Hyde Park: The "Love Luvv Bubbles & Brunch" package includes a dreamy brunch for two and a bottle of champagne, perfect for a romantic escape.
• The Gwen: Their "Love in the Windy City" package offers late checkout, a $50 dining credit, and prosecco at check-in, ensuring a luxurious stay.
  

outdoor activities

• Ice Skating at Millennium Park: Embrace the winter season by ice skating at the McCormick Tribune Ice Rink, offering a picturesque setting beneath the city's skyline.
• Lincoln Park & Gangster Tour: Explore Chicago's rich history with a guided tour through Lincoln Park, delving into tales of the city's infamous past.
  

Live Music and Performances

• Valentine's Day Smooth Jazz Friday: Enjoy an evening of smooth jazz at 616 E 71st St, creating a soothing and romantic ambiance.
• Performance: Valentine's Day with Rapt In Plastic: Experience a unique performance at the International Museum of Surgical Science, blending art and history for an unforgettable evening.
  

Culinary Delights

• Moody Tongue: This establishment offers two options for celebrating Valentine's Day, featuring a hyper-seasonal menu in an intimate setting.
• Barilla's Heart-Shaped Pasta: For a cozy night in, consider cooking with Barilla's limited-edition heart-shaped pasta, adding a romantic touch to your homemade meal.
  

Budget-Friendly Option

• DIY Valentine's Day Baskets: Create personalized gift baskets using affordable items from stores like Dollar Tree and Walmart, inspired by viral trends.
• Chick-fil-A Heart-Shaped Trays: From January 27 to February 22, Chick-fil-A offers heart-shaped trays filled with nuggets, Chick-n-Minis, brownies, or cookies, providing a festive and budget-friendly meal option.