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.

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

A Streeterville riverfront hotel with an indoor heated pool overlooking the river and a family "Summer Splash" package. Coordinates estimated from the street address.

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.