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Top 5 Valentine's Day (and Anti-Valentine's Day) Date Ideas in the Chicago Loop

Whether you are celebrating Valentine's Day with a significant other or with your BFF, the Chicago Loop is full of fun things to do to celebrate love this February.   

Skate Night at Chicago Athletic Association Hotel 

Friday, February 10 & Saturday, February 11  | 6:00 PM, 9:00 PM, 9:30 PM | Chicago Athletic Association Hotel 

The Chicago Athletic Association is transforming its basketball court into a roller rink in the name of LOVE on February 10, 2017. Skate to classic love jams from Jay and Bey to LL Cool J, with rink snacks and boozy libations for purchase. Sign-up for one of the rink’s several sessions and don’t forget to bring $5 cash to rent roller skates.  

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The Empire Room Valentine's Day Dinner & Show

Sat, February 11, 2017 | 6:30 – 9:00 PM | Palmer House Hilton 

Wow your date with an evening in the very place where Frank Sinatra, Ella Fitzgerald, Judy Garland, Louis Armstrong and countless other Hollywood legends performed during their hayday. On February 11, 2017, the Empire Room at the historic Palmer House Hilton will return to its high café society grandeur with a special Valentine’s Day three-course menu, dancing, and a live performance by Sam Fazio.

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LOVE Menu at Latinicity 

Tue, February 14, 2017 | 5:00 PM – 9:00 PM | Latinicity at Block 37  

Hola love birds! Grab your sweetheart and secure your tickets for a four course dinner on Valentine's Day at Pata Negra inside Latinicity! Enjoy oysters, bacon wrapped dates, lamb chops, chicken skewers, and more!  

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Anti-Valentine's Party at AceBounce

Sat, February 11, 2017 | 7:00 – 2:00 AM | AceBounce

On February 11 2017, love will be in the air – but you won’t find it at Ace Bounce's Anti-Valentine's Party. Bring your bestie or your partner in crime and enjoy unlimited UV ping pong, 2 hours of premium open bar & passed appetizers, DJ Lee Michaels, the ‘Love Police’ locking up ‘Romantic Rebels’ and welcome cocktails designed in collaboration with Bumble.   

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Date Night Cooking Class at Macy’s Culinary Studio

Thu, February 16, 2017 | 6:00 PM – 8:30 PM | Macy’s on State St

What could be more romantic than preparing a meal with your sweetheart? This hands-on cooking class inside Macy’s Culinary Studio will guide you through a perfectly crafted cozy Valentine’s dinner.

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Photo Credits: Rose Photo (Cover and Chicago Athletic Association Photo), HiBall Events, and AceBounce


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