Blue Skies Ahead: Talking Donkeys, Galentine’s and Soul Food

Love’s in the air, and so is the onset of 50-degree spring weather — despite what any groundhog says. Grab your significant other, or yourself, and explore what the city has to offer this weekend. Love is real, and it can be found a few train stops away. 

For those looking to get away from the cliche, lovey-dovey Valentine’s events, take the train to Columbia College Feb. 13 or 14 and explore the vast array of student-made art. Food-lovers with adventurous taste buds can fall in love with an unexpected dish during Black Restaurant Week.

Looking to stay local? Loyola’s theater will be performing a Shakespearean play, where  viewers can immerse themselves in a spell-bound production in which lovers and townspeople must break free from the magic of the fairy world. 

Head down to Navy Pier, where love is only footsteps away. Enjoy a romantic dinner, an intimate ferris wheel ride and more Valentine’s day fun. Alternatively, make your way to Three Avenues Bookshop with your Galentine’s crew. 

A Midsummer Night’s Dream: Feb. 12-22

Love looks not with the eyes, but with the heart at the Newhart Family Theatre. Watch fellow Ramblers act out a mischievous wedding weekend as it unfolds into a battle for love. Showtimes are 7:30 p.m. Thursday, Friday and Saturday and 2 p.m. Sundays.

INK Fest 2026: Feb.13-14

Columbia College’s Illustration Student Group is hosting their annual INK fest, where over 90 students and alumni will showcase their personal artwork. Visitors have the chance to purchase, observe and reflect on masterpieces created by aspiring young artists. Free tickets make for the perfect chance to celebrate creativity across Chicago universities.

Chicago Black Restaurant Week: Feb. 8-22

For any lovebirds looking to make last-minute dinner reservations, Chicago is hosting their 11th annual Black Restaurant week. Foodies can explore Black-owned restaurants across Chicago, which serve everything from Jamaican, soul food and Creole-style dishes. Get out of your comfort zone and fall in love with unforgettable dishes, all while making memories with the people close to you.

Valentine’s Day at Navy Pier: Feb. 14

This Saturday, sparks will fly. Literally. Navy Pier is hosting a love-filled weekend, offering Valentine’s Day dinners, warmth by the firepit and a romantic stroll through the illuminated tunnel full of twinkling hearts and diamonds. Visitors can end their night on the Centennial Wheel while watching fireworks light up the skyline at 9 p.m. 

Galentine’s Night at Three Avenues Bookshop: Feb. 13

What’s better than a wholesome night with the friends you love? Three Avenues Bookshop is hosting a Galentine’s Night Friday, filled with a night of community, crafts and books under candlelight. Attendees can connect with other book lovers while creating and filling a “treat yourself” bag or decorating a “treat yourself” book. There will be sweet treats, note cards, art supplies and flowers galore.