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Chicago Experiences

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Cloud 9 Living's Chicago experiences make any day in the Windy City memorable!

Unleash an inner daredevil with action-packed outings like race car driving! Try things to do in Chicago that take sightseeing to new levels with a variety of flying experiences and scenic cruises from Navy Pier. Or explore city streets with Chicago tours that are loaded with food, art, fun facts, history & more!

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  • Get blown away by the Windy City's most memorable activities in Chicago!

    The Windy City is one of America's most sought-after destinations in the Midwest — not to mention in all of America itself. Boasting vibrant urban vibes life full of sightseeing, art and culture, shopping, Chicago tours, food, and entertainment — it's easy to see why Chi-town is a hot spot for both visitors and residents alike!

    Cloud 9 Living's collection of Chicago experience gifts offer unparalleled opportunities to encounter this fascinating city and its surrounding areas. So if you're looking to plan an unforgettable outing for yourself, or surprise someone with a unique way to celebrate a special occasion — you've found it!

    Have an urban enthusiast on your hands? A myriad of tours in Chicago showcase the Windy City's remarkable past and engaging present. Hop on a bike to make your way past top downtown highlights. Get your feet moving with walking tours that feature eclectic neighborhoods and tasty food samples. For a more romantic spin on sightseeing excursions, book an evening on a scenic dinner cruise from Navy Pier. Or marvel at iconic Chicago attractions, as you enjoy a sunset paddling tour on the Chicago River, beside your special someone? With topics like food, drinks, art, architecture, culture, secrets, scandals, hauntings, history, and more — this kind of sightseeing can't be beat!

    And don't miss out on the most unique things to do in Chicago by air! Enjoy breathtaking landscapes right from the sky-high pilot's seat, while learning to fly a real airplane. Watch the Illinois sunrise from the basket of a hot air balloon, complete with a traditional champagne toast upon landing. Soar over the Chain of Lakes, Libertyville, and Lincolnshire on a luxurious aerial tour to Lake Geneva. Or take the scenic route to the top of the Willis Tower — with an exclusive Chicago tour by helicopter!

    And the thrills don't stop there! For Chicago experiences that come with plenty of adrenaline, check out skydiving, hang gliding and zip lining, take to the lake for kayaking and boating, or head to the famed Chicagoland Speedway to burn rubber in a race car. And for those whose heart skips a beat on the fairway, check out a golf lesson with a real PGA Pro!

  • Eat, drink and be merry alongside traditional sightseeing, with these top tours and activities in Chicago!

    Still trying to figure out what to do in Chicago this weekend? Let the Windy City's wide array of delectable food and drink outings decide for you. Unique Chicago events like walking city tours, scenic cruises, biking adventures, and more are your ticket to the best food and drink the city has to offer!

    Fancy a food tour? Take a delectable stroll through Chicago's fascinating neighborhoods, ambling through the likes of Bucktown, Wicker Park, Printers Row, Lincoln Park, River North, Hyde Park, and The Loop. Devour succulent food and drink samples, while also digesting captivating fun facts about the areas on top Chicago tours. Enjoy cultural cuisine while sauntering through ethnically-rich areas like Devon Avenue, Little India, and Chinatown. Mow down a classic Chicago-style pizza. Satisfy a sweet tooth with a chocolate tour. Dare to take on dishes that flaunt an "exotic" flair. Hop on a bike and pedal for bites and brews, admiring renowned Chicago attractions along the way! Or immerse yourself in the Windy City's riveting past by sipping through a Prohibition-style cocktail tour.

    Add a creative splash to a traditional date ideas with romantic things to do in Chicago like dining cruises. Combine sightseeing with a luxurious yacht, and the result is an elegant afternoon or evening on the pristine waters of Lake Michigan. Guests will delight in a delicious dinner, brunch or lunch cruise from Navy Pier. Featuring gourmet cuisine, cash bars, on-board entertainment and uninhibited views of the city skyline, an outing like this is truly second to none.

    Care to dine in the comfort of your own home? Chicago experience gifts from Cloud 9 Living make it happen! Let the gourmet magic come right to your kitchen as a professional chef prepares either a gourmet dinner party or a private, 3-course dinner for two. Sip on fine wine and socialize, entertaining guests with an in-home wine education class or an elegant tasting party!

    With foods like these hittin' the plates and palates of the Windy City, it's no wonder these appetizing things to do in Chicago bring big "bon appétit" wishes!

  • Cloud 9 Living is your one-stop shop for adrenaline-packed things to do in Chicago!

    From fast cars to flying high overhead, skydiving to soaring in hot air balloons, and everything in-between—the Windy City offers plenty of Chicago experience gifts that get the heart racing and leave a lasting mark!

    Of course, nothing says "adrenaline" quite like flying activities in the Windy City. Prepare for take-off with a number of exhilarating ways to defy gravity. Admire the marvelous view from thousands of feet in the air, as a hot air balloon gently floats you across the sky. Try a helicopter or airplane flying lesson that puts you right into the pilot's seat for the hands-on instruction of a lifetime. Or freefall high above Chicago on a skydiving excursion! If jumping from a real plane isn't ideal, then indoor skydiving is a fantastic alternative — and one of the most fun things to do in Chicago as a family! Can't get enough of feeling like you're "flying"? Soar among treetops and ravines on a zip line tour in Bemis Woods.

    Let loose on the waters of Lake Michigan with fun H2O activities! Paddle a kayak between towering skyscrapers, admiring the city's sites from a breathtaking, new perspective. Board a classic sailboat at Belmont Harbor, swapping crowded streets for fresh air on a stylish deck space as you glide swiftly across open waters. Is "super-fast" more your speed? Then when it comes to Chicago sightseeing, a high-speed thrill ride has your name written all over it! But don't blink, or you'll miss the stunning view of the skyline and surrounding Chicago attractions as the flashy vessel zips away from Navy Pier and across the water!

    Many of the most heart pounding things to do in Chicago also come with lots of engine-revving! Straight from the hot asphalt in nearby Joliet, race car driving is by far one of the top attractions in Chicago. Put dreams of fast cars, freedom and checkered flags to the ultimate test — right on the track itself! Boasting 1.5 miles of open road as a classic D-shaped tri-oval track, the Chicagoland Speedway is the perfect setting to experience the most horsepower-packed events in Chicago! As one of the nation's ultimate racing destinations, enjoy the extreme thrill of Indy and stock car ride alongs and drives. Or for those exotic car buffs, Cloud 9 Living's Chicago experience gifts also invite folks to hit up the Autobahn Country Club to drive some of the world's flashiest sets of wheels!

  • Looking for 'par-fectly' relaxing things to do in Chicago? Look no further.

    Whether you're looking to hone your own skills, or are in search of the perfect Chicago experience gift for a golf guru you know, Cloud 9 Living offers terrific golf opportunities to make it happen.

    Available for every level of experience — from rookie to 'rockin' the course weekly'—and tailored to fit any focus of the game, a golf lesson with a real PGA pro is one of the top things to do in Chicago that should be on any golf-lover's bucket list!

    This special, one-on-one instruction takes place on the practice range of one of several renowned courses, conveniently located within driving distance of the Windy City. Customized to fit the participant's appropriate level of playing, the lesson is aimed at enjoyment as well as effectiveness. Lessons typically feature topics like equipment, club grip, posture, short game strategies (pitching and chipping), swing and putting techniques, fairway and course obstacle navigation, and reading ball flight. The fundamentals covered will vary across participants, based upon a blend of the student's personal goals, as well as assessment and advice of the Pro, leading to a truly authentic golf experience in Chicago.

    The courses and their practice ranges are grand Chicago attractions themselves — sights not to be missed! Boasting the expertise of qualified PGA professionals, lessons are conducted on some of the richest fairways, well-manicured landscapes, and most challenging holes that Chicago courses have to offer. Check out Cloud 9 Living's complete list of Chicago-based PGA pros and their home courses for further details regarding available instructional locations.