Spring is here, with temperatures hitting the delightful 50s. It’s the perfect time to enjoy a weekend out in the city, whether with a partner or solo. Love is palpable everywhere, just a train ride away!
If you’re looking to skip the usual Valentine’s Day routines, check out Columbia College on February 13 or 14. Student artists will showcase their creative work, which is a fantastic way to support young talent.
Prefer to stay local? Loyola’s theater is putting on a Shakespeare play. It’s a captivating journey through love and magic, just right for those enchanted by classic tales.
Navy Pier is another great spot. Enjoy a romantic dinner or take a ride on the Ferris wheel. If you’re gathering your friends, Three Avenues Bookshop hosts events perfect for a fun Galentine’s night.
A Midsummer Night’s Dream: Feb. 12-22
Join fellow students at the Newhart Family Theatre. Enjoy a whimsical story about love and mischief with showtimes Thursday to Sunday. It’s a great chance to see local talent shine.
INK Fest 2026: Feb. 13-14
At Columbia College, the INK Fest celebrates creativity. Over 90 students and alumni will display their artwork. Plus, it’s free, making art more accessible to everyone in Chicago.
Chicago Black Restaurant Week: Feb. 8-22
This is the 11th year of Black Restaurant Week. Discover a variety of Black-owned eateries around the city. It’s a delicious way to explore different cuisines, from Jamaican to soul food.
Valentine’s Day at Navy Pier: Feb. 14
On Saturday, Navy Pier will have a special celebration. Enjoy romantic dinners, cozy fire pits, and a stroll through a lit tunnel. Finish the evening with fireworks from the Centennial Wheel at 9 p.m. — a perfect way to cap off a lovely night.
Galentine’s Night at Three Avenues Bookshop: Feb. 13
For those with a close-knit group of friends, Three Avenues Bookshop will host a Galentine’s Night. Attendees can enjoy crafts, sweet treats, and conversation in a cozy atmosphere.
As we celebrate love in all forms, these events remind us how connections enrich our lives. Whether through art, food, or shared experiences, there’s plenty to enjoy this weekend!

