1. Wrong: Chicago where she was born has the best restaurants.
Better: Chicago, where she was born, has the best restaurants.
Explanation: Much to everyone's dismay, there is only one Chicago. Therefore, the "where she was born" doesn't add essential information to the sentence and should be separated with commas.
2. Correct: The road with the six purple houses leads directly to the asylum.
Explanation: Because most roads do not have six purple houses, the descriptive phrase is necessary to the meaning of the sentence.
3. Wrong, if I have only one uncle: My uncle who wears a beret teaches Spanish.
Better, if I have only one uncle: My uncle, who wears a beret, teaches Spanish.
Explanation: In the first sentence, the lack of commas indicates that the description is necessary to the meaning of the sentence. If the speaker has only one uncle, she should separate "who wears a beret" with commas. If she has more than one uncle, she should omit the commas.
4. Wrong: In the waiting room where I found a whole cheesecake I had a feast.
Better: In the waiting room, where I found a whole cheesecake, I had a feast.
Explanation: Probably only one waiting room supplied this speaker with a whole cheesecake, so the adjective clause should be separated with commas.