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Couple Activities & Gifts in Chicago

Browse Cloud 9 Living's unique things to do for couples in Chicago & create another lifelong memory. Brewery & food tours, art classes, & more - these experiences are perfect for couples looking for fun or romance, or as gifts for friends & family.

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No markups, no added fees. You'll pay the same price as buying directly from our experience providers, but with the flexibility of easy returns and exchanges.

  • Chicago: the city that’ll blow you away both literally and figuratively. It’s no surprise The Windy City is one of the top destinations for couples to experience together. Whether it’s tasting downtown’s most incredible food and drink, cruising by boat on Lake Michigan, or experiencing Willis Tower from a bird’s eye view, Cloud 9 Living offers plenty of unique outings for any couple. 

    Dinner and a movie was so last year. Cloud 9 Living creates moments that will last a lifetime; whether it’s getting “lost in the sauce” (and cheese) during a Chicago-Style pizza tour, or celebrating the fact that alcohol is still legal during a Prohibition Cocktail Tour! Amp up date night (or “date day!”) by gifting your favorite couple the opportunity to explore some of the hottest cocktail bars and restaurants the city has to offer! 

    Leave the busy streets behind to experience Chicago’s skyline from the serene waters of Lake Michigan. Cloud 9 Living’s champagne brunch cruise, dinner sail, sunset paddle, and kayak tours, are perfect for couples looking to adventure around the lake like never before! For the couples willing to venture to new heights, give the gift of some of the most romantic views of Chicago. Cloud 9 Living offers memorable hot air balloon rides and helicopter flights guaranteed to bring the happy couple that much closer together!

    No matter the occasion, Cloud 9 Living offers only the best experiential gifts for all couples to enjoy!