Chicago, Illinois: 12 Incredible City Experiences
Get a whirlwind taste of all things Chicago in these must-see attractions.
Chicago is a place of architectural masterpieces, exciting skylines, world-class museums, incredible performances, delicious restaurants and unbeatable shopping experiences. No matter what you desire, Chicago has exactly what you’re looking for. These 12 attractions will help you check off your city-wide bucket list whiles also familiarizing you with the lay of the land.
Chicago 360 Observation Deck
Located in the John Hancock Building at the Magnificent Mile, 360 Chicago is the place to go for the most immersive and breathtaking views of Chicago’s skyline. Ascend 305 meters above the street and take your turn on TILT – an enclosed moving platform made out of glass that tilts you right over Michigan Avenue. While there, take part in the interactive learning experiences to increase your knowledge about the city’s rich history, colorful neighborhoods and architecture. This is one sightseeing excursion you don’t want to miss.
Art Institute of Chicago
Founded in 1879, the Art Institute of Chicago is the second largest museum in the USA. It houses more than 300,000 pieces of art including the most prestigious collection of American impressionist and post-impressionist paintings. Other outstanding exhibits include: Art of the Americas, a collection of Mesoamerican and Andean ceramics, sculpture, textiles and metalwork; Japanese screens and paintings; and a robust contemporary art collection that features iconic works from 1945 to present.
For families with kids, try out the Journeymaker – an innovative digital interactive experience that allows you to create your own one-of-a-kind adventure with the works of art at the museum. Choose from among eight different story lines and create a personalized family museum tour.
There are also three restaurants located in the museum and audio guides in Chinese, French, Spanish and English.
Big Bus Tours Chicago
Enjoy the beauty of Chicago when you board the Big Bus tour bus. Ride on the rooftop deck for fantastic 360-degree views of the city’s iconic skyscrapers and Lake Michigan. At 14 stops located next to key landmarks and attractions, you can hop on and hop off wherever you like. Get off at the Magnificent Mile for some shopping, the Field Museum for some natural history, Adler Planetarium to gaze at the stars and planets or Millennium Park to take a selfie at “The Bean” (officially known as “Cloud Gate”). It’s a fun and flexible sightseeing tour that can’t be missed.
A Big Bus Chicago tour stopping at the iconic Navy Pier
Blue Man Group
The Blue Man Group is a popular performance arts group that performs in more than 20 countries and has been seen by more than 35 million people around the world since 1991. The show is a dynamic combination of art, music, comedy and technology. This unique, multisensory experience is continually refreshed with new music, stories and instruments so even if you’ve seen a Blue Man Group performance before, chances are you haven’t seen this one.
Multisensory experience at the Blue Man Group Chicago shows
Founded in 1893, the Field Museum aims to “accumulate and disseminate knowledge about the preservation and exhibition of art, archeology, science and historical objects.” Located next to the Chicago Park area near the city’s center, it is in a lakeside museum complex that includes the Shedd Aquarium and the Adler Planetarium. The Field Museum features the largest and most complete T. Rex fossil in the USA.
There’s lots to do at the Field Museum: Get a bug’s-eye view in the Underground Adventure, explore Egyptian tombs, discover the Hall of Jades, experience the Ancient Americas, go on an immersive 3D adventure or get hands-on at the Grainger Science Hub.
Chicago’s First Lady Cruises
Board the First Lady cruise ship to experience the “top tour in Chicago and one of the top 10 tours in the U.S.” according to TripAdvisor. This 90-minute trip on the Chicago River will take you through the real story of Chicago’s architecture and history. Take stunning photos as your tour guide points out the architectural highlights along the way. The cruise ship offers indoor and outdoor seating as well as a full bar on board.
90-minute sightseeing trip on the Chicago River with First Lady Cruises
Fashion Outlets of Chicago
A five-minute drive from O’Hare International Airport will take you directly to the Fashion Outlets of Chicago. This outlet mall features 130 shops including Bloomingdale’s, Forever 21, Neiman Marcus Last Call and Saks Fifth Avenue, as well as a host of world-class brands like Gucci, Prada, Tory Burch, Nordstrom, Michael Kors and Burberry all at enormous discounts. It’s the perfect place for the budget-conscious fashionista to visit.
Macy’s State Street
Macy’s on State Street is a National Historic Landmark. This flagship destination is a true American original filled with the best in fashion, cuisine and more. While you’re shopping, admire the building’s Tiffany vaulted ceiling that is made from over 1.6 million pieces of colorful iridescent glass. Check the time on one of the Great Clocks outside the store – icons that were memorialized in Normal Rockwell’s “The Clock Mender.” Take a break from shopping to eat at the impressive Walnut Room – the very first restaurant located in a department store.
There are special events that take place throughout the year, including holiday celebrations in November and December and an annual flower show in March and April.
The Centennial Wheel
The Centennial Wheel located at Navy Pier is a Chicago landmark remade for the modern age. The centuries-old Ferris wheel has been turned into a massive wheel that travels 61 meters in the air, offering unparalleled panoramic views of the city skyline and Lake Michigan. The wheel is open year round with enclosed gondolas to provide a comfortable experience for guests.
While there, be sure to take a look around Navy Pier. There are more than 20 restaurants and food vendors, as well as live entertainment, rides, games, shopping and public art.
The landmark Centennial Wheel at Navy Pier
Odyssey Cruises on Lake Michigan offers lunch, brunch and dinner cruises so you can taste freshly prepared cuisine while seeing gorgeous views of the city from the water. Enjoy some light music while dining and head to the dance floor when you’re done as a DJ turns up the volume and plays some recognizable favorites. Head to the rooftop lounge and relax for a bit while you sail along and take in the amazing Chicago skyline.
The Shedd Aquarium boasts more than 30,000 different species of aquatic animals from all over the world including various types of beluga whales, tarantulas, sea turtles and more. Sign up for a 4-D experience to immerse yourself in various aquarium-themed shows. Go to an aquatic presentation to see how the beluga whales, sea lions, dolphins and other animals are cared for. You can even reach out and touch a stingray, sturgeon and sea star at the Animal Encounters exhibit. The exhibits at the Shedd Aquarium will connect you to incredible aquatic animals from around the world.
Shedd Aquarium on the shore of Lake Michigan with the Chicago skyline as a backdrop
Take a cruise down the Chicago River on a Shoreline Sightseeing Architecture tour. Get an insider’s glimpse into the buildings, architecture and engineering that makes Chicago the birthplace of the skyscraper and home of modern American architecture. This tour has multiple departures from the Navy Pier and Michigan Avenue Bridge.