Chicago boasts a fantastic dining scene, and there’s no better time to experience it than on Valentine’s Day. Book a table at one of the city's top romantic restaurants, such as The Signature Room at the 95th, which offers breathtaking skyline views, or Gibsons Italia, known for its delicious Italian cuisine and elegant ambiance.
For a fun and active date, head to Maggie Daley Park’s ice skating ribbon. Glide hand-in-hand with your special someone while taking in the picturesque cityscape. Be sure to book your skating reservation in advance, as it’s a popular Valentine’s Day activity.
Enjoy the stunning city skyline aboard a special Valentine’s Day dinner cruise on the Chicago River or Lake Michigan. Many cruises offer gourmet meals, live music, and spectacular views, making it an unforgettable experience.
Immerse yourself in world-class art at the Art Institute of Chicago, one of the most romantic places in the city. Stroll through the galleries, admire masterpieces, and perhaps find inspiration in the museum’s iconic painting, A Sunday on La Grande Jatte by Georges Seurat.
For a more low-key yet intimate experience, visit one of Chicago’s hidden speakeasies. Try The Violet Hour for expertly crafted cocktails in a dimly lit setting or The Library at Gilt Bar for a cozy and vintage-inspired vibe.
Chicago’s entertainment scene is thriving, and a live show can be a fantastic way to celebrate. Enjoy a Broadway-caliber performance at the Chicago Theatre or laugh the night away at The Second City, one of the most famous comedy clubs in the country.
Indulge your sweet tooth with a chocolate tasting tour around the city. Visit spots like Katherine Anne Confections or Vosges Haut-Chocolat to sample some of the finest handmade chocolates while learning about the art of chocolate-making.
Treat yourself and your partner to a luxurious spa day at one of Chicago’s top spas, such as The Peninsula Spa or AIRE Ancient Baths. Enjoy massages, hot baths, and other relaxing treatments to unwind and connect with your loved one.
If you want to go all out, book a stay at one of Chicago’s luxury hotels for a romantic getaway. The Waldorf Astoria, The Langham, and The Peninsula all offer special Valentine’s Day packages with champagne, spa treatments, and fine dining experiences.
Sometimes, the simplest activities are the most meaningful. Take a scenic walk through Lincoln Park, visit the Alfred Caldwell Lily Pool, or enjoy the peaceful Chicago Riverwalk at night, illuminated by the city lights.
No matter how you choose to celebrate, Valentine’s Day in Chicago offers endless opportunities to create special memories. Whether it’s a fancy dinner, an adventurous outing, or a simple walk by the lake, the Windy City is the perfect backdrop for romance and fun.
How are you planning to celebrate Valentine’s Day in Chicago this year? Let us know in the comments!
