Kansas City, Mo. 

Kansas City, Mo.  jazz
Ted Spiegel/Getty Images

Kansas City’s barbecue tastes even better with music — and both are top-notch in this city of about 480,000. Most nights you can catch everything from blues to country to jazz, pop and more. Jazz lovers will want to head to the Blue Room in K.C.'s Historic 18th and Vine Jazz District, which swings with live music performed by both up-and-comers and well-seasoned pros. (It's also right next door to the American Jazz Museum.) When you're hungry, there are plenty of restaurants serving good BBQ, but the most popular include Jack Stack BBQ, Oklahoma Joe’s Barbecue and B.B.’s Lawnside BBQ, which offers live blues with its pulled pork every night.

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Indianapolis

Indianapolis canal walk
Dave Lauridsen

Just about a two-hour drive north of Louisville, Ky., and three hours south of Chicago, this capital city of 865,000 has plenty to offer and is easy to navigate: Downtown is within walking distance of the major sports arenas as well as the NCAA Hall of Champions (there are lots of sports lovers here), the adjacent Indiana State Museum for entertaining science exhibitions and the Indianapolis Museum of Art. Also impressive is the Indianapolis Cultural Trail, a wheelchair-accessible eight-mile path that leads away from downtown to six distinct cultural districts with the allure of museums, delicious food and unique shops.

Milwaukee

Milwaukee, Wisc.  Oriental theater

Once known mostly for manufacturing and big breweries, this open-hearted city on Lake Michigan is now a “mini-Chicago,” locals like to say; with a population of about 600,000 (compared with the Windy City's 2.7 million), it increasingly provides many of the benefits of that big city just a 90-minute drive south, but for much less money. A short to-do list would need to include the Milwaukee Art Museum; the Historic Third Ward, for art galleries and fun places to grab a bite; and RiverWalk, an urban trail that cuts through the city on both sides of the Milwaukee River. Also fun: brewery tours and the many festivals held throughout the year (the biggie for music is Summerfest).

Cincinnati

Cincinnati Music Hall
Dave Lauridsen

A city is never all about one neighborhood, but an old German area in Cincinnati called Over-the-Rhine has managed to turn this town around — encouraging investment and drawing new residents to its gentrified coolness. OTR, as locals call it, is now a vibrant, carefully cultivated 319-acre mix of condos, apartments, restaurants, bars and shops, many in renovated 19th-century brick Italianate buildings. The city of nearly 300,000 is also home to the world-class Cincinnati Symphony Orchestra and Cincinnati Opera, a new Shakespeare Company theater that’s modeled after London’s Globe Theatre, and the Cincinnati Art Museum, established in 1886 and boasting 167,000 works of art.