There are few more dramatic urban landscapes than the hip windy city of Al Capone and High Fidelity. Skyscrapers decked like dominoes stand tall on the banks of Lake Michigan while the Chicago River cuts through the heart of downtown, separating your business district from your shopping and entertainment on the North Side. Check out Near North and Gold Coast, the artists' lofts and galleries of River North and the charming Old Town. Cool cocktail and cigar bars roll along the streets here like smoky riffs from a jazz guitar and there's an air of classy cool to the populace. Check out spots like Signature Lounge and Sage for high Chicago style.