Valentine’s Day Itinerary

Valentine’s Day Itinerary

Plan the Perfect Valentine’s Day Weekend in Chicago

Stumped for what to do for Valentine’s Day weekend? This year we’ve compiled a list of some of the best things to do during the holiday weekend. Whether you’re looking to spend a romantic weekend away with your significant other or a enjoy a staycation in the city with your gal pals, enjoy a memorable Valentine’s Day in Chicago at The Blackstone. View our guide below to start curating your trip.

Visit a Museum

As one of the biggest hubs for art and culture in the US, Chicago is home to a range of innovative and inspiring museums. From classics like the Art Institute of Chicago and the Field Museum to more experiential museums like the wndr museum and the U.S. Pizza Museum, spend the holiday weekend exploring some of Chicago’s coolest destinations.

Explore the City

For the adventure seekers, spend your Valentine’s Day weekend exploring the best sights and experiences in the city. Kick off your tour of Chicago with trips to Cloud Gate (The Bean) and Hyde Park. Be sure to stop by the “kissing rock” in Hyde Park – the site of Barack and Michelle Obama’s first kiss – for a sweet photo-op. Next on your day of exploration, take a lap around the Maggie Daley Park ice skating ribbon, for a classic Chicago Valentine’s Day experience. Or opt for a view from above as you explore the city via helicopter. No matter how you choose to get around, Chicago is sure to offer up a day of unforgettable memories.

Embark on Culinary Excursions

Valentine’s Day is a holiday of indulgence, and Chicago offers up endless opportunities to treat your palate to the rich and decadent local flavor. Delight in a private chocolate tasting at Vosges or learn the art of craft cocktails during a cocktail class at KOVAL Distillery. Enjoy a romantic dinner with your significant other or an intimate night out with friends at local favorite restaurants including Mercat a la Planxa, Sepia, Proxi, and Eleven City Diner.

Discover Unique Chicago Experiences

Experience something truly unforgettable during your Valentine’s weekend in Chicago. Unwind and find your bliss with your loved one at the extravagant Aire Ancient Baths, which features thermal baths, massages, and other holistic rituals. Couples can also pick up a new skill together during an Ignite Glass Studios glass blowing class. Or opt for a night at the theater – for less! Chicago Theatre Week takes place from February 7 to 17 this year, allowing you to save on some of the best entertainment in the city.

Whether you want to unwind, explore, or experience, there is no shortage of excitement to be found in Chicago during Valentine’s Day weekend. Plan your weekend in Chicago using our Stay in Love package and enjoy room upgrades, complimentary sangria, champagne, and more with your Valentine’s stay.

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