Few holidays instill last-minute dread and panic like Valentine’s Day. Thankfully, we’ve got the cure to what ails you. Not only is Chicago hosting a slew of nontraditional V-Day events including a fetish fair and a sad song sing-along, it's also home to a number of non-holiday-themed events like the NBA All-Star Weekend and Chicago Black Restaurant Week, so you can ignore the holiday in style should you choose. Here's everything you need to do in Chicago this weekend (and here's everything you need to do in Chicago all winter-long).
Discover your favorite new meal during Chicago Black Restaurant Week
Now through Sunday, February 16
Various locations
African-American owned eateries in Chicago and the surrounding area are highlighted at this immensely tasty annual event featuring an assortment of mouthwatering meals including catfish dinners, jerk chicken nachos, banana pudding, and much more (see full list here).
Cost: Prices vary
Do Valentine’s Day a little differently at venues around town
Friday, February 14
Various locations
Whether you want to listen to sad songs while playing shuffleboard and eating food truck grilled cheese at Royal Palms’ Lonely Hearts Club Sad Sing-A-Long, check out a queer variety show at an art museum during Odd Pleasures: A Queer Valentine’s Day Event at the MCA, hit up a fetish pop-up shop at a leather museum with kink education sessions and beer the Leather Archives & Museum’s Valentine’s Day Fetish Pop-Up Fair, destroy customizable punching bags and piñatas while rocking to dance music at Recess’ Stupid Cupid: Anti-Valentine’s Day Party, or watch strangers air embarrassing personal secrets during Mortified’s Doomed Valentine’s Day Show at Sleeping Village, Chicago has got you more than covered in the unusual Valentine’s Day events category. Or you could always just go out to dinner.
Cost: Prices vary
Feast like a king at Eataly’s Caviar Day
Friday, February 14
Eataly
Free guided tastings and discounts on Calvisius caviar are the order of the day at this fancy-pants Valentine’s Day event that will put that grocery store box of chocolates to shame.
Cost: No cover
Go beyond the gas station at the Chicago Champagne and Sparkling Wine Fest
Friday, February 14
I|O Godfrey Rooftop
One of Chicago’s most beautiful rooftop bars hosts this Valentine’s Day sampling of champagnes and sparkling wines. No word yet on whether or not your favorite gas station brand will be available, but we’re guessing not.
Cost: $79-$99
Party like a rock star during NBA All-Star Weekend
Friday, February 14-Sunday, February 16
Various locations
It’s been 32 years since the NBA All-Star Game was hosted in Chicago, and the city is going all out. In addition to the All-Star Game being played at the United Center Sunday (with Common introducing the players and Chance the Rapper performing at halftime), a host of shows and late-night parties will be hosted across the city including DJ Khaled at TAO Chicago and Migos at Clutch Bar Friday night, Diesel (aka Shaquille O’Neal) Saturday night at Concord Music Hall, and 2 Chainz Sunday night at Prysm. There’s even a Sneaker Summit celebrating basketball and sneaker culture during the game Sunday at Emporium Wicker Park.
Cost: Prices vary
Bring your BFF (best feminist friends) to Galentine’s Day
Saturday, February 15
Empty Bottle
Feminist Happy Hour hosts this annual Valentine’s Day-themed event with feminist comics, musical guests, a pop-up shop, bakery treats, and more.
Cost: $8
Drink in the good old days at Vintage Beer Fest
Saturday, February 15
Delilah’s
Spend the day sampling more than 100 beers from 50+ breweries -- primarily strong ales, barrel-aged brews, sours, and live beers -- at this 22nd annual event in one of Lincoln Park’s coolest bars.
Cost: $20 for 20 sample tickets
Hit up one of Chicago’s most 'Chicago' events at Sausagefest 2020
Saturday, February 15
Haymarket Pub & Brewery
Few things could be more Chicago than eating more than two dozen sausages (half made from Haymarket in-house and half “guest sausages” from local restos like Kaiser Tiger and Kimski) paired with 10 cheeses and 30+ beers and ciders in the middle of winter.
Cost: $60
Get into the pot at Sheffield’s 12th annual Chili Cookoff
Sunday, February 16
Sheffield’s
Bring your own chili to this community tasting event, with tastings open to the public and prizes awarded by a panel of esteemed judges including Doug Sohn of Hot Doug’s.
Cost: $20 for chili tastings plus two drinks
Do your own Leonardo da Vinci on ice at Paint the Ice
Sunday, February 16
Gallagher Way
How often do you get the chance to paint an ice rink? This family-friendly annual event celebrates the end of the winter ice skating rink at Gallagher Way outside Wrigley Field, with a public skate followed by live painting (paint provided).
Cost: Free
Sign up here for our daily Chicago email and be the first to get all the food/drink/fun in town.