Fellow procrastinators, did you drop the ball on Valentine’s Day plans? Never fear, the Hey Chicago Last-Minute Date Guide is here! Whether you’re single or with your forever person, we have ideas for everyone.
Best dinners: Cafe Bionda in South Loop or Truth Be Told in Woodlawn Getting a dinner reservation on Valentine’s Day is no easy feat … especially the day of. Hey Chicago found a couple spots though!
Best fam fun: Dance & crafts in North Park, Irving Park, and Garfield Park Take the kids to dance together and make art.
Best activities: Art yoga in West Town or stepping in North Lawndale
Tired of eating out and want to do something different? Take your date to do yoga and meditate at an immersive exhibit or learn to step.
Best singles event: Hot Potato Hearts citywide
The potato–themed group has speed dating, live dating shows, and book clubs year-round.
Best Galentine’s/Palentine’s: Bon Vivant Cakes in Albany Park
Bring friends to cookie- and cake-decorating workshops as well as themed happy hours. (Catch a Mariah vs. Ariana happy hour Thursday!)
The Best Last-Minute Chicago Date Ideas

Sidney Madden

The Chicago skyline 😍 (Pixabay / Stockvault)
Share article

Stay connected to City Cast Chicago and get ready to join the local conversation.
Chicago's Best
Hidden Gem Swimming Spots
Underrated swimming spots in Chicago this Summer.
The Hot Dog Cart-icle
Hot dog carts are rare in Chicago. Consider visiting one this National Hot Dog Day!
5 Queer Chicago Poets You Should Know
These local queer poets are worth checking out — during Pride month and beyond.
Welcome to The Belmont and Decibel — AKA New Berlin
Decibel is now open in the former Berlin space on Belmont. Comparisons are inevitable.
Chicago Was — Is? — a Magic Town
The Hand & The Eye is a new venue marketing Chicago-style magic. But what is Chicago-style magic?
Chicago’s Splashiest Water Activities
As we mourn the Humboldt Park swan boats, there are still plenty of Chicago water and boat activities to enjoy as the season heats up.
Celebrate Poetry in Chicago
Every month is Poetry Month in Chicago. But since April is actually National Poetry Month, consider diving in deeper.
Where You Can Still Bowl in Chicago
There are just about a dozen bowling alleys left in Chicago. Lucky for us, though, they’re as fun as ever.
The latest in Chicago
The Latest Candidates Running For Mayor
Mayor Brandon Johnson officially launched his reelection campaign, joining a race that includes roughly a dozen other challengers.
Take This Week's Chicago News Trivia Quiz
How closely were you paying attention to this week's current events in Chicago? Test yourself in our weekly trivia quiz.
Sheep Cult Comics Celebrates Local Chicago Comic Artists
Stepping into Sheep Cult Comics, you’re surrounded by whimsical, winding caverns of cloud-like shelves, presided over by sculpted sheep h...
Your Guide To Chicago’s Comic Book Stores
I’ve compiled a list of stores where you can find the newest graphic novels, affordable used comics, or even your next favorite board gam...
Mayor Brandon Johnson Answers YOUR Tough Questions
Mayor Brandon Johnson told City Cast Chicago he’ll announce whether he’s running again Sept. 13. And that’s not all he said. We sat down...
Your Guide To Karaoke Bars in Chicago
Whether your perfect karaoke night involves performing to an entire bar or renting a room for a more intimate experience, you’ve got opti...
The Art of Karaoke
Karaoke is pretty serious business, and I want to make sure you know what you’re getting yourself into.
Your Guide to September 2026 in Chicago
A guide to things to do in Chicago in September 2026