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10 unexpected Valentine's Day dates in Chicago

If you're getting tired of the old dinner and a movie routine, spice up your Valentine's Day with some unconventional date ideas


Valentine's Day falls on a Tuesday this year, but that doesn't mean you have to settle for the traditional romantic dinner and sappy movie. Unconditional love is great, but there's no excuse for subjecting your bae to boring date after boring date (especially on Valentine's Day!). Whether your partner is someone who loves to dance, dance, dance or the kind of person whose idea of a romantic evening involves arts and crafts, these unexpected date ideas are guaranteed to spice things up. 

RECOMMENDED: More Valentine's Day ideas

Valentine's Day date ideas

Things to do

Party with Dixie at Sidetrack

Celebrate Valentine's Day at Sidetrack with Dixie, dancing and drinks. You and your date can jam together to your favorite songs from the ‘90s and early 2000s, or get on stage and lip sync your way into the history books. And since there's no cover, you can spend all your cash on that special someone.

empty bottle
Photograph: Martha Williams
Music, Rock and indie

Dance the night away

It's the most romantic day of the year, and the Empty Bottle is celebrating with one hell of a dance party. The Valentine's Day lineup includes sci-fi rockabilly outfit Super Sonic Space Rebels, throwback punks the Lizzies and alt-country tunes from Bremer and the No Goods. And, you can make the night extra special by reserving a table for two at the adjacent Bite Cafe.

Crown Liquors
Photograph: Andrew Nawrocki
Things to do, Quirky events

Sing to your heart's content

Cry your eyes out while belting out a tearful rendition of Otis Redding's "These Arms Of Mine" at Another Sad Love Song Karaoke. Come alone (or bring your valentine) and enjoy $2 Old Styles (perfect for catching your tears in) while listening to some mournful tunes. Admission is free, but donations will be accepted to benefit the Chicago Women's Health Center.


Blow some glass

There's hardly a more intimate act than that of creation, and you'll be able to do just that at Ignite Glass Studios on Valentine's Day. The studio is hosting a class in which couples will work together to create a single glass heart of their own design while sipping on some bubbly and munching on chocolates. The class will not teach you how to make a water tobacco pipe, though. If that's what you're looking for, just head to one of the city's best smoke shops

Comedy, Musical

See V-Day edition of Cupid Has a Heart On

Whether you're in a relationship or single, this shamelessly provocative show will serenade you with Cupid classics and hilarious new numbers straight from the Chicago Sketch Comedy Festival. You and your date will share some laughs while you listen to feisty, sex-positive songs about life, love and relationships. We promise it will be a pants-dropping good time.

Rick Majewski
Things to do, Classes and workshops

Learn how to dance

Spice up your Valentine's Day plans at this hour-long group salsa and rumba class, complete with sparkling wine and hors o'oeuvres. Ballroom Dance Chicago has everything you need for a romantic Valentine's Day.

David Bowie
David Bowie
Music, Rock and indie

Give no Fu*ks about Love and Hate

Remember the music of David Bowie this Valentine's Day during this tribute to the Starman's wonderfully androgynous and accepting world view. Here's hoping that the show includes a renidition of Bowie's cover of Nat King Cole's "Nature Boy," which contains the classic line, "The greatest thing you'll ever learn is to love and be loved in return."

Photograph: Courtesy CC/Wikimedia Commons/Science and Society Picture Gallery

Get intimate with some ghosts

A lot of people associate Valentine's Day with roses, chocolates and cuddling, but the folks over at Chicago Hauntings Bus Tour associate it with one of the bloodiest massacres in the history of the city. The two-hour tour visits the sites of some of the most gruesome events in the city's history, so if you and your lover get off on getting the heebie jeebies, this date will be killer.

Things to do

Paint a lovely picture

Spend a very special Valentine's Day sipping on cocktails and making works of art with your loved one. This romantic, BYOB, Parisian-themed painting party will start with a cocktail reception, followed by hours of painting with your sweetie. And don't forget, the couple that paints together, stays together.


Rev up your engine

On the surface, the Chicago Auto Show sounds about as romantic as a dinner at IHOP. But the sleek, shiny cars, the phallic gear shifts and the sound of pistons and crankshafts thrusting wildly should leave you and your date feeling like Nicolas Cage and Angelina Jolie in that strange sex scene in Gone in 60 Seconds.