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The highlights from my point of view, in no particular order:

Lake Michigan (including the Outer Drive and the many parks along it), ethnic foods and neighbourhoods, Hyde Park (yeah, yeah, we stole the name) and University of Chicago area, music of all kinds, architecture.

For many area and architecture tours, including the very popular Chicago River Cruise (seasonal, of course – brrrr!), and for architecture information, see the Chicago Architecture Foundation which has an office at 224 South Michigan Avenue in Chicago’s downtown (not technically in Chicago’s famous Loop which is defined by the elevated train tracks downtown). They are in the Santa Fe building; while in the downtown area see the Rookery (in both it and the Santa Fe building be sure to see the lobby areas inside), Monadnock Building, Carson Pirie, Scott Building.

The Chicago Architecture Foundation 'tour' pages will give you plenty of ideas for visits and their tours are high quality and reasonably priced.]]> http://www.ivebeenthere.co.uk/tips/20758 http://www.ivebeenthere.co.uk/tips/19472 http://www.ivebeenthere.co.uk/tips/19472 http://www.ivebeenthere.co.uk/tips/19471 http://www.ivebeenthere.co.uk/tips/19471 http://www.ivebeenthere.co.uk/tips/19468 http://www.ivebeenthere.co.uk/tips/19468 http://www.ivebeenthere.co.uk/tips/17399 http://www.ivebeenthere.co.uk/tips/17399 http://www.ivebeenthere.co.uk/tips/4213
It is primarily a museum and performance space, with a busy schedule of exhibits and performances. On Saturdays, they often have midday dance classes for young and old (great fun, even if you just watch).

The Chicago Symphony and Opera both offer free performances in the opulent Preston Bradley Hall, covered in glass mosaic, beneath the world's largest Tiffany dome.]]> http://www.ivebeenthere.co.uk/tips/4213