Chicago vs Hawaii

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.

Hawaii is the ultimate winter escape for Americans: no passport, no currency exchange and 80°F (27°C) days while the mainland shivers. Choosing an island is the first decision. Oahu is the energetic hub, with Waikiki's beach scene, the moving USS Arizona Memorial at Pearl Harbor, the Diamond Head crater hike and the North Shore, where winter swells send 30-foot waves rolling into Waimea Bay and the Banzai Pipeline. The Big Island is raw and vast, with active volcanoes at Hawaii Volcanoes National Park, night snorkeling with giant manta rays off Kona and stargazing near the summit of Mauna Kea. Maui, with the Road to Hana and Haleakala sunrise, is the romantic middle ground and deserves its own trip. This 7-day plan pairs 3 nights on Oahu with 4 nights on the Big Island, linked by a short inter-island flight of about 45 minutes. Book the key reservations early: Pearl Harbor's USS Arizona Memorial program, Diamond Head entry for non-residents, and a manta ray tour. Pack a light jacket for volcano evenings, mineral reef-safe sunscreen for the reefs, and plenty of patience for traffic in Honolulu.