7 Spectacular Date Ideas – Valentine’s Day in Chicago

Let’s face it, planning what to do for Valentine’s Day can be a challenge. Thankfully for us, we live in Chicago where there’s no shortage of things to do. Check out this list of some of the best happenings this year, and let us know if we missed anything!

Date Night at Ignite Glass Studios (2/10-2/14)

Tired of the cliché candlelit dinner on Valentine’s Day? Date Night at Ignite Glass Studios may be just what you’re looking for! Each couple will work together to create a glass heart of their own design. Of course, you will get to indulge in complimentary sparkling wine and chocolates while you work on your masterpiece.

This year’s workshops are almost sold out, so book your session ASAP! For more info, you can head here.

The 11th Annual Hideout Makeout Party (2/11)

If you and your significant other enjoy live music, this is the Valentine’s Day event for you.   An orchestra of local musicians will be coming together at The Hideout to perform a selection of original music, film soundtracks, and love songs. The Hideout is great because its small space creates an intimate setting perfect for the holiday.

Head here for more information on the event.

Cupid’s Undie Run (2/11)

Feeling crazy enough to run a mile in your undies in February? Well, you’re in luck. Cupid’s Undie Run is taking place on Saturday, February 11th with an after party to follow at John Barleycorn. What’s more, you will be raising money for the Children’s Tumor Foundation, which is a great cause.

For more info on Cupid’s Undie Run, head here.

Chicago Pizza Party (2/11)

When you live in Chicago, it only feels natural to make pizza a part of your Valentine’s Day celebration. Luckily for you, the Chicago Pizza Party is happening on Saturday, February 11th offering the opportunity to try all of the city’s best pizza. All of Chicago’s pizza joints will be competing for the title of “Best Pie in Chi” so you know they’ll be bringing their A-game.

For more info on the event and to buy tickets, head here. 

The Naked at the Art Museum Scavenger Hunt (2/11)

Looking to be inspired this Valentine’s Day? You may want to check out The Naked at the Art Museum Scavenger Hunt. This scavenger hunt encourages you and your significant other to explore the Art Institute and find all the scantily-clad works available. Along the way, you’ll also get a chance to pick up tidbits of art history.

For more info on the scavenger hunt, head here.

Empty Bottle Valentine’s Day Dance (2/14)

Interested in dancing the night away while raising money for a good cause? The Empty Bottle Valentine’s Day Dance could be the holiday outing for you! The Super Sonic Space Rebels, whose music spans from rockabilly to full-on punk rock, will headline the night. Proceeds from the show will benefit Rape Victims Advocates.

For more info on the event, head here.

Another Sad Love Song Karaoke @ Crown Liquors (2/14)

Looking to do some performing yourself? Whether or not you have a significant other, this event is sure to be a blast. Just make your way to the stage and belt out your favorite love song. In case you need some liquid courage, Old Styles are only $2. Admission is free, but donations will be accepted to benefit the Chicago Women’s Health Center.

For more information on the event, you can head here.


Written by @properties
@properties Christie’s International Real Estate is Chicagoland’s #1 brokerage. Through our affiliation with Christie’s International Real Estate, our network spans nearly 50 countries. No matter your real estate needs, we’ve got you covered.