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This is really a matter of personal taste.

Objectively, the only way to really measure is by what people will pay to live somewhere. It can be hard to compare directly, because some areas are mostly high-rise, while others are mostly single-family homes. But, in general the most expensive neighborhoods in the city, in no particular order, tend to be:

Lincoln Park, Lakeview, the Gold Coast, Streeterville, River North, Wicker Park, Bucktown, Andersonville, Hyde Park, the Loop, Lincoln Square, the South Loop and the West Loop.

There are also a number of extremely expensive suburbs, but I'm less familiar with them.

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Q: What are the best neighbourhoods in Chicago?
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