


Set sail on Lake Michigan aboard this authentic 148-foot tall ship for an unforgettable hands-on sailing adventure. Kids can help hoist the sails, take the helm, and learn maritime skills from the crew while experiencing what life was like aboard historic sailing vessels. It's an educational and thrilling experience that gets children off screens and into real-world adventure on the water.
Weekday morning or early afternoon sails are less crowded than weekends. May through September offers the best weather, with calmer waters in early summer. Sunset cruises are magical but book well in advance as they sell out quickly.
Moderate pricing with family packages available. Navy Pier parking garages are within walking distance. No food service onboard, but you can bring water bottles. The ship is not wheelchair accessible due to its historic design and requires climbing aboard.
Operates primarily from May through October, weather permitting. Sailing season typically runs late spring through early fall. Winter months have limited or no operations. Special themed sails and events may be offered during peak summer season.
Navy Pier (just steps away) has numerous family-friendly options including Giordano's for Chicago deep-dish pizza and Harry Caray's Tavern with a kids menu. For quicker bites, the pier's food court offers everything from hot dogs to ice cream.
Navy Pier is Chicago's ultimate family entertainment destination, spanning 50 acres along Lake Michigan with attractions for all ages. From the iconic 200-foot Centennial Wheel offering breathtaking city views to the charming vintage carousel, plus interactive museums, boat cruises, and seasonal festivals, there's enough here to fill an entire day of family fun.
Skydeck Chicago puts you on top of the world at the Willis Tower, where kids can stand on The Ledge,clear glass boxes that extend out from the 103rd floor, letting them see straight down to the streets below. It's an exhilarating experience that combines breathtaking views of the entire city with the thrill of feeling like you're floating in mid-air.
360 CHICAGO offers stunning views from the 94th floor of the John Hancock Center, featuring the thrilling TILT experience where kids can lean out over Michigan Avenue in a slowly tilting glass and steel platform. The observation deck provides interactive touchscreens to identify landmarks, and the floor-to-ceiling windows offer spectacular views of Lake Michigan and the city skyline.
Millennium Park is Chicago's ultimate family-friendly destination, combining world-class art installations with interactive features that kids absolutely love. From taking silly photos in the reflective Cloud Gate sculpture (The Bean) to splashing in the Crown Fountain's giant video faces that spray water, this 24.5-acre park offers endless entertainment without costing a penny.