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Celebrate Love with Chicago’s Sweetest Day Events

Why wait until Valentine’s Day to celebrate the ones you love? In Chicago, you don’t have to wait. In fact, Sweetest Day (Saturday October 15th) is approaching quickly! Sweetest Day gets less fanfare than Valentine’s Day, but it is still a holiday to celebrate the ones you love. Lucky for you, our list of events will rekindle those friendships and help you connect with loved ones. Whether you are meeting someone new or bringing the spark back to a long-term relationship, these Sweetest Day events are for you!

#1: Stay at The Godfrey Hotel and Dine at Their Rooftop Lounge, I|O Godfrey

Whether you’re celebrating Sweetest Day with friends or looking for a romantic dinner and stay, The Godfrey Hotel has it all. The Godfrey Hotel offers stunning rooms and amenities, including their “Bubbles + Dessert,” package. This package treats you to Moёt & Chandon mini splits and two delicious cake flavors, Red Velvet and Devil’s Chocolate. Open for all seasons, their I|O Rooftop Lounge provides one-of-a-kind views of downtown Chicago. You can’t go wrong with their shareable menu, complete with their Steak Frites and the I|O Cosmo. This rooftop is perfect for getting your friend group together or taking someone on a date. Head here to book a hotel room, and go here to make reservations at their rooftop lounge!

#2: Singles Speed Dating at Walking Queens Dance Workshop

Are you looking to meet someone on this Sweetest Day? Look no further because The Walking Queens Dance Workshop has you covered! Head on over to their dance studio for a night of meeting new people in a low-pressure environment. Take this opportunity to make the most of being single and meet new people that might spark your interest! Speed dating games will run from October 14th at 8:00 pm until midnight, perfect for an all-night event or a short stay. Participants must be 21 or older, and all sexual preferences are welcome. Plus, for $25, you can enjoy all the food, drinks, and dancing you want. Hurry over to EventBrite to buy your tickets because they are selling out fast. This Sweetest Day is the time to break out of your comfort zone and meet someone new!

#3: Channel your creative energy with Sweetest Day Paint & Sip at Canvas by Boo’tek

If you and your partner love to be creative, head to Canvas by Boo’tek to enjoy their Sweetest Day Paint & Sip! All painting supplies are provided with your ticket, and all levels of experience are welcome. With your $120 ticket, you and your partner receive a 2-hour painting event, one canvas to take home, and savory treats, including champagne! Plus, they are offering sessions at 6:00 pm and 8:00 pm on October 15th, so you can celebrate according to your schedule. Once you pick a time, you and your sweetie can show up with your BYOB bottle. If you are ready to treat your partner to a night of creativity, fun, and love, head over to Canvas by Boo’tek’s Page to purchase your ticket!

#4: Sweetest Day Dinner & Dance Class presented by Oaken Bistro and Bar

If you’re looking for a Sweetest Day event a little outside the city, Oaken Bistro and Bar will help get your groove on. Instructor Denita Inez will teach you and your partner how to follow each other’s rhythm. This class is perfect for beginners, and you can even show off to your friends. After the dance lesson, dinner will be served at 7:00 pm. Complete with two entrees, two glasses of wine, and dessert, this event will leave you with unforgettable memories. If this sounds like something you are curious about, Oaken Bistro and Bar is the place for you. Treat your sweetie to a night of togetherness at Oaken Bistro and Bar!

#5: Laugh at the Sweetest Day Comedy Jam

If you and your partner love stand-up comedy, the Arie Crown Theater has the event for you! With shows on October 14th and 15th, the Arie Crown Theater will bring you never-ending laughs while celebrating your love. Their lineup includes Ricky Smiley, B. Simone, Jess Hilarious, and so many more. Plus, their performers are complimented with great ticket prices, ranging from $75 to $200. If you have never seen standup comedy or if you are a diehard fan, these tickets are for you. The Sweetest Day Comedy Jam gives you and your sweetheart the ability to share laughs together and explore new entertainment. Hurry over to their website to grab some tickets and learn more about the lineup for each day!

Written by: Maddie Belland


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