Museum of Ice Cream Chicago

The below-street-level original Billy Goat Tavern near the Wrigley Building, famous for its counter-service cheezborgers, reached only by a flight of stairs.

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

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

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.

Retro diner where the servers sass the guests and dance on the counters, and the tiny hot fudge sundae comes in a glass kids keep.

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