Pacific Coast Highway vs Chicago

Driving the Pacific Coast Highway from Los Angeles to San Francisco is the classic American road trip, a roughly 450-mile ribbon of asphalt that clings to cliffs, dips into surf towns and threads some of the most dramatic coastline on Earth. Start with the beach cities of Santa Monica and Malibu, then roll north to Santa Barbara's red-tile roofs and its graceful Spanish mission. Next come the laid-back college town of San Luis Obispo and the wide sands of Pismo Beach, followed by the hilltop opulence of Hearst Castle and hundreds of elephant seals lounging on the beach at Piedras Blancas. The highlight is Big Sur, where Highway 1 winds high above the ocean past McWay Falls and the arching Bixby Creek Bridge before reaching storybook Carmel-by-the-Sea and the world-class Monterey Bay Aquarium. Five days is the sweet spot for the drive, with extra days for San Francisco, Napa Valley wine country and the coast south of the city. One important warning: landslides regularly close sections of Highway 1 in Big Sur, so check Caltrans QuickMap before you set out and be ready to detour inland on US-101 or do Big Sur as an out-and-back from Carmel.

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.