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However, when you look at a city like Chicago, it really has no trendy or hip suburbs or neighboring cities. The closest would be Evanston or Oak Park, and they are very nice suburbs with things to do, but most people would not consider them hip, trendy or cool.
Naperville would like to have a word with you.
Also, you can't just write off Oak Park and Evanston. They aren't just "nice" suburbs, they are some of the most liberal suburbs in the entire country and have plenty of bars, clubs, and trendy restaurants/shops in their downtown areas. Especially Evanston with Northwestern being literally right there.
Oak Park and Evanston can settle for being nice, urban suburbs. Nothing particularly cool about either.
Home Alone was in Winetka.
Oak Park is fairly "cool", though I will agree it's mostly viewed as being a suburban family town that happens to have big city amenities like Metra/CTA access and being very walkable/bikeable. That said, I do believe Oak Park will become more "cool" as more and more of the west side becomes gentrified, especially from the east.
I think writing off Evanston as only being a "nice suburb" is laughable. It's also a college town that is definitely moving away from the "old money" suburban stereotype a lot of people typically associate with every suburb along the north shore.
Naperville's downtown is truly remarkable and I believe definitely passes for being considered "cool", even knowing Naperville as a whole is still seen as a typical white collar and sprawly suburb/ ex-burb. It's definitely become the best downtown core in the entire Chicago area easily, and definitely has become trendy with the amount of bars, restaurants, and stores that have, and continue to open up there.
yikes... I don't think Charlotte has one. Davidson is somewhat cool but the housing stock resembles a usual suburb. All the trendy areas in Charlotte are inside city limits and Ballantyne probably doesn't fit this description. If you consider Chapel Hill a suburb, then maybe the Triangle has met this. Can't think of any suburb in SC either. For Atlanta, it might be Decatur(?)
Does Houston have "trendy" suburbs? I feel like the city limits are so far out, any areas of high activity will probably be in the city proper, and this goes for a lot of Southern and Western cities.
The Woodlands, Galveston, even Sugar Land.
The Woodlands is very trendy, the shopping areas are very different from the rest of the metro and the Woodlands is a very popular place for concerts.
Galveston has the nightlife, beaches, Waterpark, moody gardens, antique spots.
Sugar Land is a lot more new, but up and coming. It is trying to develop an identity with amenities such as minor league sports teams, hosting concerts and its town Square is gaining popularity with festivals.
Katy has its spots but those are largely unincorporated and undefined areas.
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