Things to Do on Valentine’s Day in Chicago: A Guide to Romance and Adventure

Jan 22, 2025

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Valentine’s Day in Chicago is a magical experience filled with romantic possibilities and exciting adventures. Whether celebrating with a significant other or a group of friends or treating yourself to a day of love and self-care, the Windy City offers something for everyone. 

From intimate dining experiences to thrilling activities, this guide will help you create unforgettable memories.

Enjoy a Romantic Dinner at About Last Knife

For a memorable Valentine’s Day dinner in Chicago, indulge at About Last Knife, the modern steakhouse inside Arlo Chicago. The restaurant offers a chic yet cozy atmosphere, perfect for an intimate date night. 

Savor expertly prepared steaks, creative small plates, and signature cocktails that set the mood for romance. After dinner, extend the evening with a stay at Arlo Chicago for a truly unforgettable experience.

Take a Romantic Stroll at Millennium Park

Bundle up and walk leisurely through Millennium Park, one of Chicago’s most beloved landmarks. Snap a selfie in front of the iconic Cloud Gate sculpture (also known as “The Bean”), and enjoy the serene atmosphere of the park’s winter landscape. 

If you’re up for a little adventure, lace up your skates and hit the ice at the McCormick Tribune Ice Rink for a classic winter date.

Enjoy a Couples’ Spa Day

Pamper yourselves with a couples’ spa day at one of Chicago’s luxurious spas. The Waldorf Astoria Spa and the Chuan Spa at The Langham are two excellent choices, offering a range of treatments designed to relax and rejuvenate. 

From soothing massages to invigorating facials, these experiences provide the ultimate in self-care and connection. Your special someone is sure to be pleased with this choice. 

Explore the Art Institute of Chicago

If you and your partner are art enthusiasts, spend some time at the Art Institute of Chicago. This world-renowned museum houses an impressive collection of masterpieces, from Monet’s serene water lilies to Grant Wood’s iconic “American Gothic.” 

Stroll hand-in-hand through the galleries and let the beauty of the art inspire your own love story. It’s sure to impress your loved one. 

Indulge in Sweet Treats at Chicago’s Dessert Spots

No Valentine’s Day in Chicago is complete without a little indulgence. Stop by Mindy’s Bakery for artisanal pastries and cookies, or head to BomboBar for creative dessert offerings like hot chocolate bombs and gelato-filled donuts. For a more classic treat, try the decadent chocolates at Vosges Haut-Chocolat or the famous cupcakes at Molly’s Cupcakes.

Take a Romantic Cruise on the Chicago River

For a unique perspective of the city, book a Valentine’s Day cruise on the Chicago River. Several companies offer themed cruises featuring dinner, drinks, and live music. The illuminated skyline provides a stunning backdrop for your evening, creating a truly magical experience.

Watch a Show at the Chicago Theater

Cap off your evening with a live performance at the historic Chicago Theater. From Broadway musicals to stand-up comedy and concerts, there’s always something exciting happening on this iconic stage. Check the schedule beforehand and secure tickets for a show that suits your style.

Savor the City’s Culinary Delights

Chicago’s dining scene is diverse and vibrant, offering something for every palate. If you’re in the mood for classic Italian cuisine, book a table at RPM Italian. For a more contemporary dining experience, try Girl & the Goat, known for its bold flavors and innovative dishes. Nothing inspires love like a tasty meal!

Enjoy a Private Wine Tasting

For wine lovers, a private wine tasting is a perfect Valentine’s Day activity. Check out City Winery or Chicago’s Wine Goddess for an intimate evening of fine wines paired with delicious snacks. These experiences are both educational and romantic, allowing you to discover new favorites together.

Take in the Night Sky at Adler Planetarium

End your Valentine’s Day in Chicago by gazing at the stars. The Adler Planetarium offers special evening events, including stargazing sessions and immersive shows that explore the wonders of the universe. Sharing this awe-inspiring experience with your loved one is the perfect way to conclude a romantic day.

Make Valentine’s Day in Chicago Unforgettable with a Stay at the Arlo Chicago

Start your Valentine’s Day getaway with a stay at the chic and stylish Arlo Chicago. Nestled in the heart of downtown, the Arlo Chicago combines modern luxury with cozy comfort, making it the perfect base for your romantic escapades. 

The hotel’s sophisticated design and top-notch amenities set the tone for an indulgent celebration. Plus, its prime location puts you within walking distance of many of the city’s best attractions, ensuring your day is both convenient and memorable.Chicago is a city that knows how to celebrate love. With its blend of culture, adventure, and romance, the possibilities for your Valentine’s Day are endless. Whether you choose to dine in style, explore the city’s iconic landmarks, or simply relax together at the Arlo Chicago, your time in the Windy City is sure to be unforgettable.