Loop Chicago


Plan your Romantic Sweetest Day in the Chicago Loop

Sweetest Day is this Saturday, October 21. We bet you didn't know that this Valentine’s Day-like holiday originated and is most widely celebrated in the Midwest. So don’t be too hard on your Boston beau or Los Angeles love, if they don’t already have your Saturday planned out. We have got you covered with these unique date ideas for a romantic Sweetest Day in the Chicago Loop. 

Share a Day at the American Writers Museum

180 N. Michigan, 2nd Floor 

Treat your sweetie to a visit to The Beat Journey: Jack Kerouac’s “On the Road” exhibit at the American Writers Museum. View the original manuscript scroll through November 4. The gift shop has a multitude of items that will make your book-loving bae swoon.

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Challenge Your Date to a Game of Ping-Pong!

230 N. Clark St. 

Head to 1901 and have a fun dinner in the upbeat environs of AceBounce on Wacker & Clark. Afterwards, fan the flames of romance with the heat of competition: challenge your date to a game of Ping Pong. Up the anty and make it interesting by playing each other for future dates, kisses, or just getting your significant other to be on laundry duty for the next month.

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Celebrate Your Love for Halloween & Art at the Arts in the Dark Parade

Columbus Drive at dusk, traveling from Balbo Ave. to Monroe St.

We all know that couple that really loves Halloween – they spend hours making costumes, carve pumpkins, and go all out with the spooky decorations. If that sounds like you and your Sweetest Day Sweetie, The Arts in the Dark Parade is the perfect way to cram even more Halloween into your October. This festive and enchanting nighttime Halloween Parade along Columbus Drive, on Saturday, Oct. 21 from 6-8 p.m., will showcase the creativity of Chicago’s diverse cultural community with costumes, masks, spectacle, music, movement, lighting elements and plenty of audience engagement.

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Share a Romantic Meal at tesori trattoria & bar

65 E. Adams St. 

We all know that that the quickest way to the heart is through the stomach, so celebrate your Sweetest Day with a romantic meal at tesori trattoria & bar. This Italian-inspired restaurant offers a unique menu that borrows from Italy’s various regional influences and traditions to create an authentic experience. All of the restaurant’s pastas are made in house including their lasagna, strichetti and ravioli.

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For even more Chicago Loop date ideas click here

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