Things to do in Chicago
Discover amazing Chicago activities and premium in-home experiences.
Cradled by the breezes of Lake Michigan, Chicago rises in an energetic sweep of gleaming towers and historic neighborhoods, where every block thrums with a rhythm all its own. Here, bold city spirit meets Midwest warmth—inviting you to savor skyline sunsets, soulful jazz drifting from open doors, and the irresistible pull of deep-dish comfort beneath wide Midwestern skies.
Popular Activities in Chicago
Chicago Historical and Architectural Lake & River Tour
Discover Chicago's iconic skyline and rich history on a narrated lake and river cruise
Chicago West Side Foodie Bike Tour
Sample Chicago favorites while cycling through vibrant Near West Side neighborhoods on a fun 4-hour guided ride
37ft Rinker Fiesta Vee Private Yacht Charter
Cruise Chicago waters with up to 13 guests for a flexible three-to-four-hour outing
In-Home Experiences
Gateway to the West Loop Food Tour
Taste iconic dishes from award-winning chefs while exploring Chicago's vibrant West Loop with a local guide
Explore the Vibrant Heart of Chicago
Chicago is a city where architectural marvels meet vibrant neighborhoods, offering an urban tapestry rich with history and culture. As you stroll along the shores of Lake Michigan, you'll feel the gentle breeze that brings life to this bustling metropolis. The skyline is a masterpiece in itself, showcasing iconic structures like Willis Tower and John Hancock Center against a backdrop of endless blue waters.
In summer, Millennium Park becomes your playground—home to outdoor concerts at Jay Pritzker Pavilion and reflective moments by Cloud Gate (affectionately known as "The Bean"). Autumn paints Lincoln Park's trees in fiery hues, perfect for leisurely walks or picnics near its tranquil lagoon. Winter transforms Navy Pier into a wonderland adorned with twinkling lights while spring invites you to explore the lush Garfield Park Conservatory.
Dive into Chicago’s culinary scene by sampling deep-dish pizza or savoring flavors from around the world in neighborhoods like Pilsen and Chinatown. Catch live jazz echoing through historic clubs or discover art at renowned institutions such as The Art Institute of Chicago. Whether you're cruising down the river on an architecture tour or cheering at Wrigley Field under sunny skies, every moment here feels uniquely alive—a testament to why this city captures hearts time after time.