Billy Goat Tavern

Deep-dish pizza and a dessert kids remember: a warm chocolate chip cookie pizza topped with ice cream.

A ticketed, multi-room interactive attraction near the Tribune Tower built around ice-cream-themed installations, including a room filled with plastic sprinkles. Strollers must be left outside that room.

A Chicago River and lake architecture cruise departing at the Michigan Avenue Bridge, with stroller storage and restrooms on board, run by the same family company since 1935.

A historic Michigan Avenue tower hotel known for its ornate 1929 indoor pool, one of the oldest and largest hotel pools in the country.

A paved promenade along the Chicago River downtown, with the PlayCubes climbing structure for kids alongside boat tours and riverside dining.

A large riverfront convention hotel in the Loop with connecting rooms and a crib available on request, though it does not have a swimming pool.