Family Weekend Fun in Chicago: 2-Day Itinerary with Kids Itinerary

Start your family weekend with a bird's-eye view of the city at the 360 Chicago Observation Deck (Formerly John Hancock Observatory). After taking in the skyline, head to Sweetwater Tavern & Grille (Michigan Plaza - Chicago) for a hearty breakfast to fuel your day.

Spend the afternoon cruising the Chicago River on an architecture tour. Marvel at the city's famous skyscrapers and learn about their history. For lunch, enjoy a picnic at the serene Grant Park, or grab a bite at Cindy's Rooftop with its stunning views.

Conclude your day with a visit to the lively Navy Pier. Let the kids enjoy the rides and attractions, and catch the fireworks if it's a Saturday. For dinner, indulge in classic pub fare at Miller's Pub in the nearby Loop area.