Chicago Experiences

The third biggest city in the US by population, Chicago gives New York a run for its money with a breath-taking skyline hugging the shores of Lake Michigan. Chicago has a pulsating music scene and a fine collection of eateries.
Chicago is a gateway city for some of America’s great journeys, Route 66 starts here, or board the California Zephyr Train bound for San Francisco, alternatively head South towards the Mississippi and the delights of Memphis and New Orleans.

Below is a small selection of the tours we can organise for you when you have booked your USA holiday with us and are visiting Chicago.  

Navy Pier is where you go in Chicago for events, free public programs, attractions, culture, dining, shopping and more. It's where fun lives large, whether you're a visitor or local, with family or friends. As a nonprofit organization, the People's Pier offers a diverse and eclectic range of activities and experiences that ignite the imagination, stimulate the senses and allow your spirit to soar. It's no surprise it's a place that continues to inspire discovery and wonder after more than a century. Find out what it has to inspire you...

Navy Pier is the People’s Pier, Chicago’s lakefront treasure, welcoming all and offering dynamic and eclectic experiences through partnerships and programs that inspire discovery and wonder. Since its reopening in 1995, more than 180 million guests have come to enjoy the Pier's 50 acres of unparalleled attractions and experiences. In 2022, Navy Pier continues to evolve into an accessible, year-round centerpiece for Chicago’s diverse arts and cultural treasures.  

Willis Tower captures the vibrancy of the city under one roof. From street to sky, it provides inviting hospitality and memorable experiences. It is an urban destination in the heart of downtown, delivering the best experiences of life and work to residents and visitors of Chicago.

Willis Tower is the heart of downtown Chicago and the future of work and play. The 110-story building is one of the tallest buildings in the world and the second tallest building in North America, making it impossible to miss when appreciating the city’s skyline.

Willis Tower Highlights

  • The Ledge, a series of windows that extend from the building offering views straight down over the city of Chicago.
  • On a clear day, views can span 50 miles and four states: Illinois, Indiana, Wisconsin and Michigan.
  • Guests can enjoy interactive and educational attractions that celebrate Chicago’s sports, architecture, history, food, music and people.

The Millennium Park Foundation was established in 1998 as a nonprofit organization with the mission to enhance and steward Millennium Park. Millennium Park Foundation and its donors, engaged various artists and architects to design and construct the sculptures and facilities found throughout the Park. Each new addition presented its own story of vision, risk, design, finance, construction and operation. As a result, the Park is an aggregate of the initial framework and individual additions that were not anticipated in the original plan. Yet at each stage, the framework for planning was flexible and neutral enough to enable a variety of alternatives to evolve successfully.

Millennium Park Highlights

  • Open Daily, 6am to 11pm
  • Multiple exhibitions and sculptures located around the park
  • 45 minute public art walking tour available to join with a booking reservation

The Art Institute of Chicago shares its singular collections with our city and the world. They collect, care for, and interpret works of art across time, cultures, geographies, and identities, centering the vision of artists and makers. They recognize that all art is made in a particular context, demanding continual, dynamic reconsideration in the present. The institute is a place of gathering that fosters the exchange of ideas and inspire an expansive, inclusive understanding of human creativity. 


WNDR is a collective of thinkers, artists, poets and designers, working at the intersection of art and technology. The WNDR museum is an interactive experience: a multi-sensory showcase of art and technology. The museum exists to spread a simple message that at the WNDR everybody is an artist and as artists they treat their visitors as more than passive onlookers but value their contributions as forms of art. 

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  • Tell us what you'd like to see, what type of accommodation you prefer and how you'd like to travel.
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