Portillo's Hot Dogs

A budget-leaning boutique hotel in River North set inside a 1927 building, with a cafe and 24-hour gym rather than a pool.

The original 1943 birthplace of Chicago deep-dish pizza, still serving as a full-service restaurant with its own kids' menu.

Chicago's classic deep-dish pizzeria, with a dedicated kids' menu and a full-service, casual dining room that regularly seats families.

An all-suite extended-stay hotel one block off Michigan Avenue, with full kitchens in every suite and free hot breakfast, an easy walk to Millennium Park and Navy Pier.

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.