Chicago is a vibrant, bustling city jam-packed with attractions, delicious food, and endless things to do — the perfect destination city for a long weekend! You’ll find scores of things to do and see, especially in the summer, which is when the city shines the brightest.

The third largest city in the U.S., Chicago boasts impressive architecture and many public works of art, making it ideal to explore by foot. And while you can always wander aimlessly, Cloud 9 Living offers a variety of guided city tours that come with a knowledgeable tour guide plus a well-planned itinerary, giving you the most bang for your buck.

Cultural Diversity

Chicago was once a city of distinct neighborhoods with different cultures based on the immigrants who lived there. To this day, it remains a diverse and energetic city: an impressive number of pubs gives away its Irish heritage, and you’ll also find Little Italy, Greektown, Little Seoul, Chinatown, and Little India to explore.

Sites to See in Chicago

You’ll want to head to the lakefront, and Buckingham Fountain in Grant Park is one of the first things to check out. Dedicated in 1927, it’s one of the largest fountains in the world and is meant to allegorically represent Lake Michigan. From there it’s an easy stroll to Millenium Park, which is among the top ten tourist destinations in the U.S. Take time to explore the Field Museum of Natural History and its world-class exhibitions. Don’t forget Navy Pier while you’re near the lakefront — there’s an abundance of sights, activities, and food for people of all ages.

If you’re a baseball fan, you must head to Wrigley Field for a Cubs game. Even if you’re not a baseball fan, you’ll appreciate the old, historic field and the unabashed home team pride, which mysteriously persists, regardless of its performance. Shoppers will delight in Chicago’s storied Magnificent Mile, a section of Michigan Avenue that boasts 460 retailers, all within walking distance. And no trip to the Windy City is complete without a ride to the top of the Willis Tower (formerly Sears Tower), the second tallest building in the U.S.

Chicago Dining Cruises

When you visit Chicago, don’t miss the opportunity to get on the water and experience the beautiful skyline from Lake Michigan. A dining cruise is the perfect way to enjoy a few hours on the lake and a delicious meal at the same time. Cloud 9 Living offers a variety of cruises, including breakfast, lunch, and dinner — even gourmet options! Whether it’s for you to enjoy or to give as a gift, you’re sure to find the perfect fit for your schedule and budget.  

Chicago Driving Experiences

For a completely unique and one hundred percent thrilling activity, check out one of Cloud 9 Living’s Chicago Driving Experiences. Get behind the wheel of your dream car at a world-class race course. Take your pick: Ferrari, Lamborghini, NASCAR, Indy Car, Porsche, or Nissan GT-R.

Craving the speed but prefer to remain in the driver’s seat? We’ve got that too! Ride along with a professional stock car or Indy Car driver and experience the ride of a lifetime!

Ten adrenaline pumping, heart-racing driving experiences await you in Chicago. Choose from these thrilling options — you can’t go wrong!