The best things to do on Valentine’s Day

Whether you’re single, taken, or somewhere in-between, we’ve found the best things to do on Valentine’s Day
Runners streaked through Wrigleyville in their undergarments during Cupid's Undie Run, February 7, 2015.
Photograph: Max Herman

Whether you’re single or all bae’d up, making plans on Valentine’s Day is a total pain in the ass. How do you find that sweet spot that shows you put in effort without going over the top or outweighing your partner’s plans? Well, we’re here to help. We’ve assembled a list of great things to do on V-Day, from nights out at comedy clubs to cozying up at the most romantic restaurants in the city. As for what happens after the date? Well, that’s on you. 

RECOMMENDED: Our complete guide to Valentine's Day in Chicago

Valentine’s Day events and concerts

Photograph: Courtesy Navy Pier
News, Sex & Dating

Speed dating on the Navy Pier Ferris wheel

Looking for love in all the wrong places? Consider making your next love connection 200 feet in the air during a truly unique Valentine’s Day event at Navy Pier. On February 9, local singles are invited to step out of their comfort zones and onto the Centennial Wheel for a speed dating event unlike any other.

Things to do

Chicago Botanic Garden Orchid Show

The orchid is arguably the most romantic flower in the plant kingdom: It's finicky, some varieties require years to bloom and is the most diverse family of flowering plants in existence. See over 10,000 orchids here, and take advantage of the opportunity to purchase one for your sweetheart.

Photograph: Trevor Kelley
Nightlife, Cabaret and burlesque

Kiss Kiss Cabaret

icon-location-pin Uptown Underground, Uptown

There's no such thing as déjà vu at a Kiss Kiss Cabaret show. That's because no two performances are alike. But what is consistent from show to show is a mix of comedy, music, burlesque and the Kiss Kiss Coquettes. Surprise guests add to the risqué fun at Uptown Underground.

Maggie Daley Skating Ribbon
Courtesy Maggie Daley Park
Things to do

Ice skate with your date

Win a guy or gal’s heart with a pair of skates and an outstretched hand gliding down one of Chicago’s icy lovers’ lanes. Take your pick with our complete guide to ice skating in Chicago.