45 Fun Date Ideas Around Chicago for Couples

Yoli B said:  Three Dots and a Dash is located in a dark basement in River North and somehow it is one of the coolest spots in town! The bar has a tiki theme and it shows in the food and the drinks as they come out. You can take your pick between the intimate lounge or boisterous bar area! What makes this place extra special is they cold press the juice for all of there cocktail creations, and also use the freshest ingredients for everything on the menu!

Kelly R said:  Instead of popping into a bar for a drink on date night, why not learn to make your own? Hollow Leg offers hands-on mixology classes, where you can learn to make great original cocktails with a focus on local, seasonal, sustainable, and organic ingredients. Classes are held at different venues around the city and suburbs. See calendar.

Yoli B said:  Ever wonder what is behind that beautiful door in downtown Chicago? Now you can find out with Open House Chicago! One weekend a year the Chicago Architecture Center allows behind-the-scenes access to over 200 buildings around Chicago, giving you a glimpse of those never before seen tile floors or golden ceilings that are usually off limits. This event is great for design and history lovers. Don't miss it!!

Joseph Kelley said:  Have a blast and enjoy the beautiful Chicago skyline and Navy Pier on a wave runner! Licensed by the Chicago Park District, rentals are located at North Ave Beach, where you can swim, play volleyball, or have a drink at Castaways Bar & Grill too.

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Yoli B said:  Who doesn't love a good arcade? Headquarters Beercade is like your old-school neighborhood arcade on steroids! The carefully crafted cocktails and food are the perfect accompaniment to the arcade games! Some games are free so stick with those and a cocktail! As a bonus, the 80's music overhead is the perfect soundtrack for a great Chicago date night.

Kelly R said:  Kayak the Chicago River together on the Ghosts and Gangsters of Hustlertown tour, where you take in some beautiful nighttime views of Chicago while exploring the shady side of the city's past. Learn about the city’s nefarious gangsters and how one area of the river purportedly became haunted. Additional tour themes are also available.

This 2-hour kayaking tour guides you down the Chicago River as it flows through downtown. From the water level up, you'll look up to mega skyscrapers, the riverside promenade, and learn about Chicago's famous architecture while kayaking along the Chicago River. Other tours include a sunset tour, Navy Pier fireworks tour, gangsters tour, and a moonlight tour.

Kelly R said:  The Second City offers a drop-in improv class that is open to everyone, beginners included. It’s a great date opportunity that will give you a taste for improv, comedy, and get you out of your comfort zone! This two-hour class occurs near regularly on their weekly schedule.

Zoom classes are available for to your date night too, streaming straight to your couch!

Yoli B said:  Emporium is part arcade and part whiskey bar and all fun! The atmosphere is lively and the music is loud, but the vintage games add enough nostalgia to keep you going for a while. The whiskey selection is one of the most extensive that I have seen in Chicago, and the beer menu will not disappoint. If you are looking for a quieter time, show up when they open to avoid the crowds. Take a look at the game offerings and happy gaming!

Gina I. said:  Looking for a little adventure on your next date night? iFLY Indoor Skydiving is the place to be. Suit up and enter iFLY's vertical wind tunnel that creates a one-of-a-kind free fall sensation. So, you can experience the excitement of skydiving without having to jump out of a plane! Book your 'flights' on their website.

Yoli B said:  This may seem completely unconventional and quirky...because it is! Axe throwing is a favorite pastime of our Canadian neighbors and Bad Axe is the first indoor throwing facility in the country. Hop on over after dinner on-the-town, It is always a great idea to keep things exciting, so why not go throw axes on your next date night! Reservations only accepted for groups of 8+people.

Kelly R said:  Ignite glass studio offers a lot of really fun one time workshops that are perfect for a date! Explore your creative side with your loved one while making a high quality project. Nearly every weekend, too, Ignite Glass Studios presents free interactive glassblowing demonstrations. See schedule.

Gina I. said:  Take this unique opportunity together to discover the Buddhist Temple of Chicago. The temple welcomes all to join them for free 60-minutes meditation, held twice weekly - evening and morning sessions. No experience is necessary and cushions are provided. Beginners are encouraged to arrive early for an orientation, and volunteer leaders are available for questions after the sessions.

Yoli B said:  Green Mill is a jazz club that's had the likes of Al Capone in the building. Chicago is a jazz city and you will feel like you have gone back in time. Drinks are affordable and the cover at Green Mill is reasonable (cash only!).

For couples looking to try something fun and different, a secure indoor shooting range is an interesting idea to consider. This controlled environment is the perfect place to take shooting practice as a couple and see who is the better shot.