Ed Debevic's
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.
159 E Ohio St, Chicago, IL 60611
How kid-friendly is it?
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A historic Michigan Avenue tower hotel known for its ornate 1929 indoor pool, one of the oldest and largest hotel pools in the country.
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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.