I typically spend the last week of November/first week in December in Chicago every year. It is a very clean city that offers quite a bit in terms of dining, entertainment, and culture. Some things that are worth checking out are the Modern Art Museum (Art Institute), The Field Museum (Natural History), and shopping along Michigan Avenue. Chicago is a very clean city in comparison to other cities in the US of similar size. In addition, the transportation system is excellent and with a combination of subways, buses and cabs it would be possible to live in the city without a car I would imagine. Some good restaurants to try: Gene & Georgetti's and Nick's Fish Market. Great food. At Nick's, get the abalone. it is out of this world! But finally, if you have to go: try to go in the summer. The winter is cold, wet, and basically miserable. The summer must be beautiful on the lake though...
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