10 Great Places to Retire for the City Life

Experience downtown Chicago at night. — Getty Images

Chicago

In such a massive city with so many world-class offerings, you might think Chicagoans would be brusque and preoccupied. But (to risk a vast generalization) you would be wrong. Locals, on the whole, are disarmingly friendly and place a strong priority on having fun.

Cubs baseball games at Wrigley Field are packed, even on weekday afternoons, with pre- and postgame parties filling the indoor-outdoor taverns across the street. The lakefront park system — created to give all comers, regardless of wealth, access to Lake Michigan's beauty — is replete with joggers, walkers and cyclists, and tennis, softball, soccer and football games whenever the weather permits.

Blues and jazz bars, from the venerable Andy's Jazz Club to the low-key Rosa's Lounge, draw steady crowds throughout the week.

Chicago's Steppenwolf and Goodman theaters are world-famous, with superb symphony, ballet and dance offerings. The Art Institute of Chicago, which harbors weeks' worth of captivating exhibits, is free on Thursday nights and Fridays during the summer. The Field Museum of Natural History and Shedd Aquarium, both phenomenal, sit on the shores of Lake Michigan, near 12th Street Beach and Northerly Island Park.

The local variety and quality of restaurant options rivals New York, and the shops of Michigan Avenue will cause even the most frugal to unfold their wallets.

See also: The 10 most affordable cities.

Chicago's suburbs aren't too shabby, either. Naperville was ranked third in Money magazine's 2008 list of the best small U.S. cities because of the town's good jobs, affordable housing and great schools. Frank Lloyd Wright lived in Oak Park for 20 years, and the buildings he left behind make it an extraordinary place to take a walk. The village of Woodstock has lovingly preserved its Victorian homes, and its town square has a packed schedule of events.

Chicago is also home to more than 100 degree-granting institutions, led by premier schools such as the University of Chicago and Northwestern University in Evanston.

There are downsides, of course. The Chicago area has pretty nasty traffic congestion. To avoid the worst of it, you'll need to time your drives — or find housing in an amenity-rich neighborhood such as Lincoln Park.

Also, Chicago's weather can be downright inhumane in the heart of winter, and chilly fronts can push through into early May. But the city's positive energy, cosmopolitan pulse and lakeside beauty can soften the blow of any bad day.

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