Things To Do

Oak Street Beach

Randyll's favorite beach growing up, Oak Street is a beach with activities like paddle boarding, kayaking, volleyball, and yoga. You can also grab food and drinks at Castaways Bar and Grill. On a clear day, you can see the high-rises along Lake Shore Drive, the Magnificent Mile, Navy Pier, and Lake Point Tower.

Navy Pier

From recreation to relaxation & entertainment to education, Navy Pier offers activities & experiences for all. Navy Pier is home to one of Chicago’s most iconic attractions: the magnificent Centennial Wheel, offering soaring views of the Chicago skyline and Lake Michigan.

Willis Tower

Willis Tower has graced the Chicago skyline for over 50 years. Once the tallest building in the world, today it provides the best view in the country with the highest observation deck in the U.S. One of the top attractions in the city, combining a multi-million dollar Chicago museum that ranks among the best in town with a remarkable 50-mile view from our observation deck. On a clear day, you can see into 4 states!

Lincoln Park Zoo

Yankees at White Sox on 8/30/2025 (TBD)

Austin's first MLB game in Chicago cheering on the White Sox!

Cloud Gate

Giordano's

Chicago's Famous Deep Dish

Portillo's & Barnelli's Chicago

Garrett Popcorn Shops

Chicago style is the only way to go. a Chicago must-have for every visitor!

The Art Institute of Chicago

The second-largest art museum in the country, The Art Institute of Chicago has one of the most impressive collections of impressionist paintings and surrealist works of art in the world.

Clarence F. Buckingham Memorial Fountain

Sitting as the centerpiece to Grant Park is the stunning landmark known as Buckingham Fountain. The fountain was created to represent Lake Michigan and features four pairs of beautifully Art Deco style sea horses.