Chicago vs Nashville

Chicago is the American city that gave the world the skyscraper, and it still shows off its skyline better than almost anywhere. Glide along the Chicago River on an architecture cruise as guides decode Art Deco towers, glassy modern giants and the movable bridges overhead. Stroll Millennium Park to see your reflection bend in Cloud Gate, then follow the Riverwalk past cafes, kayakers and wine bars tucked below street level. Dinner means deep-dish pizza, a buttery, cheese-loaded pie that takes about 40 minutes to bake and is worth every one, though locals will also steer you toward tavern-style thin crust and an Italian beef. Evenings belong to Lake Michigan: ride a bike along the Lakefront Trail and watch the towers catch the last light at sunset. The L trains make it easy to roam without a car, from Loop landmarks to neighborhoods like Wicker Park and Lakeview. Stay longer and add the Art Institute's world-class collection, Navy Pier, a game at Wrigley Field, the lakeside Museum Campus and the free Lincoln Park Zoo. Summer brings festivals and patio season; winter brings serious cold, but also holiday markets and cozy blues clubs.

Nashville is built for a weekend. On Lower Broadway, neon-lit honky-tonks have live bands playing from late morning until well past midnight, usually with no cover, and the next great songwriter might be on stage at noon. A block away, the Ryman Auditorium, the 'Mother Church of Country Music,' offers daytime tours and some of the best acoustics in the country at night. Walk the John Seigenthaler Pedestrian Bridge over the Cumberland River at sunset for the classic skyline view, and fuel up on Nashville hot chicken, fried crisp and dusted with cayenne at whatever heat level you dare. Weekend mornings belong to brunch: grab a table in walkable 12 South, laid-back East Nashville or the sleek Gulch, then wander their murals and boutiques. Stay longer to tour the Country Music Hall of Fame and Museum, catch a show at the Grand Ole Opry, sip wine at the Belle Meade Historic Site and spend a day in Franklin, a charming Civil War-era town 30 minutes south. Spring and fall bring mild weather and packed music calendars, but Music City delivers year-round as long as you book shows and hotels early.