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Romantic Chicago Experiences for Couples

Chicago Date Night

A Cloud 9 Living Collection

Let Them Choose Their Perfect Date!

Take the guesswork out of gift-giving and let your friend or loved one choose their perfect date with this Chicago Date Night collection! 

Our handpicked selection of top-rated experiences for two allows the happy couple to select the experience of their choice and book a date convenient for them.

Whether seeking a picturesque sunset paddle or an adrenaline-filled adventure to remember - this Date Night gift has something for every type of couple!

Price: $199


Give the gift of romance with a handpicked selection of our favorite experiences for couples.


Your recipient selects their dream date and books a time convenient for them.


Go out, have fun, and create a memory to last a lifetime!

No - This Date Night gift is different from our other experience vouchers because you are giving your recipient the gift of choice! We have handpicked a collection of our top-rated experiences for couples and your recipient can choose which experience they would like to do and when.

Of course if your recipient chooses to do an experience not included in the Date Night Collection, they are welcome to exchange this gift and apply the monetary value of the voucher toward any other experience on our site.

Absolutely! The value of this package can be applied towards any experience on the site. To exchange, click on the "My Vouchers" tab in your account.  

No, but some experiences included do have differing guidelines for things like age, weight, and height. Please be mindful of these restrictions when choosing your perfect date!

No problem! Your recipient will have the balance to use for future bookings toward any experience on the site. 

Pizza & Cocktails Tour
Tour for 2
Murder Mystery Dinner Show
Dinner for 2
Architectural Kayak Tour
Kayak Tour for 2
Ultimate Zip Line Adventure Course
Ultimate Zip Line Adventure Course for 2
Prohibition Cocktail Tour
Tour for 2
Pizza Tour
For 2
Escape Room
Escape Room for 2
Bikes, Bites, and Brews Tour - North Side Route
Tour for 2
Bikes, Bites, and Brews Tour - West Side Route
Tour for 2
Fireworks Kayak Tour
Kayak Tour for 2
Best of Chicago Food Tour
Tour for 2
Fireworks Bike Tour
Electric Bike for 2
Sunset Paddle
For 2 People
River & Lake Architectural Cruise
Cruise for 2
Chinatown Food Tour
Tour for 2
Greatest Hits Bike Tour
Tour for 2
River North Food Tour
Tour for 2
Walking Food Tour
Tour for 2
Navy Pier Food Tour
Food Tour + Beer Upgrade for 2
Lakefront Bike Tour
Tour for 2
Private Art Lessons
Two 2-Hour Classes for 2
Kayak Tour at Night
For 2 People
City Lights Bike Tour
Electric Bike for 2

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$199 Chicago Date Night