Chicago vs Savannah and Charleston

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.

Two of the South's most beautiful old cities sit just two hours apart, making them an easy pairing for a four- or five-day trip. Start in Savannah, Georgia, where 22 leafy squares shaded by Spanish moss-draped oaks break up a historic district made for wandering. Stroll to the white fountain in Forsyth Park, tour a historic house that tells the full story of the enslaved people who lived there, and end the day on cobblestoned River Street watching container ships glide past. Then drive about 110 miles up the coast to Charleston, South Carolina. Walk past the pastel facades of Rainbow Row and the grand homes on the Battery, cool off at the Pineapple Fountain in Waterfront Park, and dig into lowcountry seafood: shrimp and grits, she-crab soup and fresh oysters. Plantation tours such as Magnolia, Boone Hall and McLeod Plantation are part of any visit, and the best of them center the histories of enslaved people and the Gullah Geechee culture they built. With extra days, add Sullivan's Island, the beaches of Tybee Island and Kiawah, and the quiet waterfront town of Beaufort. Spring and fall bring mild weather, blooming azaleas and comfortable walking.