Outside-The-Box Valentine’s Day

Creative ways to show your love.

Valentine’s Day has become known as the holiday of sweet treats and long, lingering dinners. If your idea of showing love expands beyond chocolate and wine, or even beyond your S.O., we invite you to think about creative ways to celebrate those you care about most that don’t involve heart candies.

And beyond February 14, there’s no reason why taking time to appreciate those you love can’t extend past one day. We like to think of the entire month of February as an ideal time to slow down and cherish your cherished ones.

Our picks on how to accomplish that? Read on below.

Game On, Game Room

As you may recall from the holiday season, the best gift in our book is an experience. Our Game Room is the original billiards room in our building and today plays host to selection of classic games, inventive cocktails and a lively atmosphere.

The Game Room experience offers two hours of reserved seating, priority game access and cocktails and bites for up to four. Whether you’re looking for an anti-chick flick Galentine’s Day or simply want to grab another couple for a fun night out, bocce and beers can be just as invigorating as champagne and caviar.

But that’s far from our only unique gift experience. Explore everything from a Friends Weekend Away to Fireside Cocktails at Cindy’s in our online shop here.

Comedy Club

February 25

Nothing says I love you like laughing together. While we think any number of our playful programming events are gift-worthy, we’ve circled the February 25 Comedy Club as an early 2022 highlight. Our vintage gymnasium will be transformed into a laugh-out-loud venue for the evening and will welcome the likes of Lucia Whalen from Ladylike Chicago, Ali Drapos from Laugh Factory and Mike Atcherson from Chicago Fight Club.

Dont Fret Mug

For those who prefer to gift an actual item, this one’s for you. We’ve teamed up with Chicago artist Dont Fret to create a limited-edition mug. Best known for his wheat-pasted characters and musings on streets in cities around the world, Dont Fret brings his whimsical style to a distinct coffee (or ahem, whiskey) mug. The Swimming style mug allows you to sip and daydream of floating carefree in a pool of fair-trade java, on warmer days no doubt. Available while supplies last for $20.

SparkLing and Oysters

February 15

Ok, this one could be considered a little more “traditional” but it so eptomizes everything Valentine’s Day should be, we had to include it. Plus, how many chances does one get to shut down Cindy’s Rooftop? For $60 per person on February 15, enjoy an intimate but exciting environment surrounded by quality food, good drinks and a welcoming atmosphere.

Thanks to our friends at Southern Glazer Wine and Spirits, we’re taking over Cindy’s Rooftop for a private tasting and oyster experience that will include five sparkling varietals from different regions of the world, paired with oysters from Island Creek that are harvested daily and shipped overnight.

Ready to share the love all month long? Tack one (or more) of the above onto a cozy guest room, our winter rates are starting from $179.


February 14

Then you’re in luck. Cherry Circle Room is opening its doors especially for the day of love. Dig into decadent treats (available all weekend and, of course, into Monday) like a bone-in 16 oz. tenderloin or porcini mushroom risotto.

From there, head on over to the Game Room for a special night of Bachelor-Themed Bingo. Comedian Kenya Elan will host “The Final Rose Bingo,” combining two of the best possible Valentine’s Day activities – watching The Bachelor and Bingo. There will be buckets of sparkling rose, red and white wine and, of course, plenty of red roses. No need to RSVP – just show up!