Unique Date Ideas in Chicago

Dinner at The Metropolitan Club

There’s no shortage of unique Chicago date ideas, which can be a bit overwhelming when you’re planning your next romantic adventure in the Windy City. Take a moment to read our tips for fun date ideas in Chicago, all of which have been sourced by seasoned locals. And then, take a moment to learn about the singular fine dining experience near the top floor of Willis Tower at Skydeck Chicago’s “The Ledge.

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See Alfonso Ponticelli at The Green Mill 

Alfonso is one of the greatest Jazz Manouche guitarists in the world, and he plays three sets every Wednesday night at the Green Mill. Accompanied by jazz fiddle, drums, and stand-up bass, his swinging Django-inspired chops will keep you and your date on the edge of your seat. Not to forget, the Green Mill is one of the most elegant, aesthetically rich clubs in all of Chicago. Once owned by Al Capone, it’s the last true 30s jazz club of its kind in the city, and a national treasure.

Relax at Aire Ancient Baths 

Truly one of the most unique date ideas in Chicago, this spa in River West features traditional Greek, Ottoman, and Roman-style baths. What’s more, these baths can range in temperature, from between a frigid 50ºF and 102ºF. Aire Ancient Baths also features an aroma therapy steam room, a couple’s massage service, and can even provide you and S.O. with a wine bath for two! 

Watch the Sunset on Chicago from the Shedd Aquarium 

The Lakeshore Path runs alongside and just below the Shedd Aquarium and Adler Planetarium. Between the path and these two museums, you’ll find a large lawn with any number of picnicking locals. It’s a popular location because it provides the aboslute best view of downtown Chicago (save for the one at Skydeck). Rest assured, there are few, if any, more unique Chicago date ideas. 

Take In Breath-taking Views at Skydeck Chicago 

One of the most unique date ideas in Chicago is dining on the 103rd floor of the Willis Tower with your significant other while you gaze at a view of four different states, Lake Michigan, and all of metropolitan Chicago. To make reservations, call Skydeck Chicago at 312-875-9447 and reserve your table three days in advance of date night! And before you go, take a moment to hear what your neighbors have to say about their Skydeck experience!