AAA Diamond Destination: Chicago, Illinois

Ah, Chicago! City of baseball, deep-dish pizza and a skyline that could pierce the clouds. Whether you're on a budget or you’re a luxury traveler, the City of Big Shoulders offers something for everyone. AAA wants to show you how to experience Chicago's vibrant energy, from free wonders to unforgettable splurges.

What to do in Chicago

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Start your day with a stroll through Millennium Park. Since opening in 2004, it’s become one of Chicago’s must-see attractions. Snap a photo with the iconic Cloud Gate (also known as "The Bean"), a giant sculpture that distorts your reflection like a funhouse mirror. Gaze at Crown Fountain, a unique video sculpture that displays the faces of Chicago residents over a reflecting pool. Finally, don't miss the award-winning Lurie Garden, a serene escape for both people and wildlife.

For more botanical delights, visit the Garfield Park Conservatory. It boasts a vast collection of plants from around the world in eight indoor gardens, plus more than 10 acres outdoors. All year round, you can marvel at lush rainforests, arid deserts and vibrant floral displays. Reservations are required, but entry is free. 

The Chicago Cultural Center stands as one of the city's most magnificent rich landmarks. Originally built in 1897 as the Chicago Public Library, the building's classic Renaissance Revival style architecture features an ornate exterior of granite and Bedford limestone complemented by an awe-inspiring interior with sweeping staircases, intricate mosaic floors and the world's largest Tiffany stained-glass dome. Today, the center operates as a premier arts venue, housing multiple exhibition galleries that showcase cutting-edge visual arts, a concert hall and even a miniature Chicago-style comedy theater. Free to the public year-round, the Chicago Cultural Center hosts hundreds of music, dance, and theater events annually, truly living up to its reputation as the "People's Palace."

Chicago's culinary scene is legendary, and you don't need to break the bank to enjoy it. Head to the AAA Approved Little Goat Diner, a casual spot by celebrity chef Stephanie Izard. You’ll find hearty all-day breakfast, refreshing salads and juicy burgers at a reasonable price. 

Indulge in modern elegance and unmatched comfort at the AAA Three Diamond Cambria Hotel Chicago Loop-Theatre District. Stay in the heart of the famed Theatre District with variety of dining, shopping, and attractions. During your stay, enjoy locally inspired décor throughout, well-equipped fitness center, spa-like bathroom, and little indulgences designed to help you stay at your best.  

Splurge

One of the city’s most famous qualities is its architecture. The birthplace of the skyscraper, Chicago is home to a diverse and beautiful array of buildings that make up its iconic skyline. And what better way to experience this skyline than a cruise down the Chicago River. Visitors can  join an expert from the Chicago Architecture Center for a 90-minute tour on a luxury vessel. You’ll hear captivating stories about more than 50 buildings 

What else is Chicago most known for? Baseball. The city boasts not only the iconic Chicago Cubs but also the beloved Chicago White Sox. While the Cubs and Wrigley Field represent a classic Chicago tradition with their longstanding presence, the White Sox bring their own storied legacy to the city's sports scene. Attending a White Sox game at Guaranteed Rate Field is an experience cherished by fans, where the thrill of being close to the action, enjoying a hot dog, and cheering alongside passionate supporters creates an unforgettable atmosphere in Major League Baseball.

The Chicago Cubs are one of the oldest baseball teams in the country, and Wrigley Field is one of the oldest stadiums — so it's more than just a game; it's a classic Chicago tradition. There’s just nothing like grabbing a hot dog, hearing the crack of that bat, and rooting for the home team among some of the most passionate fans in Major League Baseball.

To really treat yourself, head to the Magnificent Mile and enter a world of luxury brands and high-end boutiques. Stretching down 13 blocks of North Michigan Avenue, this prestigious shopping district has stores by renowned designers like Prada, Chanel, Saint Laurent and more. Whether you're seeking a statement piece or a timeless wardrobe addition, prepare to be dazzled by the sheer variety and opulence.

For an elegant dining experience in Chicago, Travelle at the AAA Five Diamond Langham Hotel is the ultimate destination. Awarded a Michelin star in 2022, Travelle impresses with a seasonally-inspired menu featuring artful presentations infused with global flavors. Situated with stunning views of the Chicago River through floor-to-ceiling windows, Travelle delivers a sophisticated culinary journey spotlighting local ingredients and inventive dishes.

For an unforgettable stay, check into the Radisson Blu Aqua Hotel. This AAA Four Diamond designated establishment stands out with its remarkable architecture designed by Jeanne Gang, featuring sculptural concrete facades that create rolling waves of curved balconies. This unique design has earned the hotel widespread acclaim, including being named the world's best new skyscrapers by Emporis in 2009. In addition to its striking aesthetics, the Radisson Blu Aqua Hotel is also notable for its eco-friendly initiatives, having achieved LEED Silver certification for its sustainable design and operations.

Take in panoramic views from their rooftop pool, soak away stress in the hot tub, unwind after a day of sight-seeing or meetings with our on-site spa services, or get your heart rate up with a game at our half-size basketball court.