Let’s face it, Valentine’s Day has lost its’ fastball. The olden days of having a single date on the calendar that couples of all types circle for romance has largely been washed away in the hustle and pressures of work, family, and more. But there are still those of us that have that sliver of romance in them, and look to this Hallmark Holiday for a chance to show that special someone you care. For those looking to spend their evening with a special someone there are a handful of Valentine’s Day date ideas around Chicago to enjoy that precious time. Here are 5 Valentine’s Day date ideas that you can make into your own special evening.

Catch a Drag Show at The Greystone Tavern

BAM! Right out of the gates with a drag show. What a fun and unique way to spend this Valentine’s Day away from the traditional dinner and a movie. Don’t be lame. Head to the Graystone Tavern in Wrigleyville for a special V-Day Drag Show. The show will feature live performances from Chicago-favorite, Merriam Levkowitz, music, and dancing, as well as Graystone Tavern’s entire food menu. Tickets are only $12 per person and can be purchased on Graystone Tavern’s website!

The Tanta Experience, a Love Story

Most Valentine’s Day plans include a dinner date. There’s nothing wrong with that. But rather than getting your usual pasta and wine or hitting your usual steakhouse, head to River North and enjoy a menu of Peruvian delights. This Valentine’s Day, Tanta is delivering a three-course prix fixe menu for $86/pp that’s sure to make you fall in love.

Dimo’s Pizza & Chill

Say you’re a couple that’s been at this for a while and in that state of “Valentine’s is a bit played out.” You can still make your night in with each other special by ordering Chicago’s very own Dimo’s and watching a dope movie that’s about Chicago, or has Chicago in it, or is definitely Chicago but they call it Gotha—The Dark Knight. I’m telling you to watch The Dark Knight and order a heart-shaped pizza from Dimo’s, get a cheap bottle of wine, and kill the lights to watch Heath Ledger be badass only to get sad about Heath Ledger and cry together. You know what I’m talking about. I’ll say nothing more.


Treat Yourself to the Perfect Staycation

Chicago has no shortage of cute boutique hotels downtown to get away for a single night. Whether you’re in need of a night in the city away from the drawl of the suburbs or you just want to enjoy an evening of intimacy that isn’t in your stale three-flat then check out a hotel in the city and parlay it with anything else on this list for a perfect evening “away.”

Aire Ancient Bathe Your Stress From the Kids Away

Those who have kids know. Whether it’s five minutes of peace or a fancy ancient Turkish bath, mom and dad need their space to breathe. Why settle for five minutes in the middle of the day when you should be treating yourself to the ultimate in self-care and relaxation. Call grandma and grandpa or a babysitter or someone to watch the kids for a bit and recharge for Valentine’s Day. It’s the perfect exercise in, “we deserve this.”


Photo by Wyron A on Unsplash


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