The cheesiest holiday to ever exist – next to Valentine’s Day of course – is this Saturday!

October 21st is officially Sweetest Day.

Originally named “Candy Day” in 1916, this day was intended to remind people to bring small tokens of affection (mostly candy) to improve the lives of those around them.

Clearly, it’s spiraled a bit from the meaning (not just the name), but the intention was to bring “sweets to your sweetheart”.

You can use this as an excuse to ask, or buy, your loved one presents, to go on a date night or simply, ignore it all together.

If you do choose to enjoy the weather and celebrate all things sweet – even if it’s just with the girlfriends – here are a few events happening in the city that you could partake in.


Sweetest Day Comedy Jam 

Not many tickets left on Ticketmaster, but if you’re interested in attending, you’ll find a way.


Sweetest Day Painting and Painting for Couples

Grab your sweetie or your girlfriends for a night of drinking and painting.


A Cruise and some Dinner

Admire Chicago’s beautiful skyline from the middle of Lake Michigan while indulging in some food and champagne!


Halloween at Navy Pier

Celebrate Halloween early at Navy Pier with two outdoor movies and fireworks!


A Beer Tasting

Check out 150 craft and import beers + live entertainment and food at Brew Moon Beer & Band Festival in McCook.


Grab a Nice Brunch/Dinner

There are so many delicious restaurants in the city. I’m sure you have a few, so plan a romantic dinner for just the two of you. Or check out some of these!



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