40 Fun Date Ideas Around Chicago for Couples

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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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.

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:  Established in 1971, this mindfulness meditation center is part of an international community of urban meditation and rural retreat centers founded by Chögyam Trungpa Rinpoche. Located in the West Loop, Shambhala offers frequent public meditation times. Shambhala Open Houses are free and open to the public; drop in with your loved one for a unique and mindful experience together.

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.

Get away without leaving Chicago! This charming bed and breakfast with spa is a perfect way to spend an overnight with your significant other. Book a room at Ruby Room and get spa treatments together which include massage and more progressive healing and energy treatments, readings, facials and more. Have dinner somewhere romantic nearby (there are numerous options).

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.

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.

Shila said:  The Chicago Magic Lounge is an adult-only bar and entertainment venue that features a calendar of events full of invigorating magic show performances. Resident magicians are on 7-days a week, and special guest performances can feature well-known magicians from around the world.

If you have kids, on Sundays, they present family-friendly showcases too. It's another great Chicago family staycation idea!

Yoli B said:  You are hearing it here first...caviar is the new "thing"! Heritage is the perfect introductory to caviar offering an affordable price point. The staff at Heritage is knowledgeable and the menu offerings are amazing. I had my reservations about caviar but thought a tasting would be fun paired with vodka of course! The fish origin story is explained along with the proper way to eat it and everything is totally approachable! We were blown out of the water (no pun intended) by all of the handmade bread, sauces and desserts at Heritage in addition to the caviar!! Yummy...

Kelly R. said:  If we learned anything from Ghost, it's that nothing brings couples together like the potter's wheel. Check out the BYOB Happy Hour workshop at Penguin Foot Pottery, where you can try the potter's wheel with instruction in a relaxed environment. You can keep up to two pieces and will have to come back to glaze your items once they have been fired. Dates are added at the start of each month and classes fill quickly.

Select Friday and Saturday nights