Chicago vs San Francisco

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.

San Francisco packs world-famous sights into a compact, hilly peninsula wrapped in fog and bay views. Ride a clanging cable car up Nob Hill, then drop toward the water for sourdough bread bowls of clam chowder at Fisherman's Wharf. Book Alcatraz well ahead, because the ferry to the former prison island and its gripping audio tour sell out weeks in advance. Walk or bike across the Golden Gate Bridge, coast downhill into Sausalito for seafood by the bay and ride the ferry home past the skyline. Give a full day to wine country, sipping Cabernet in Napa Valley or Pinot Noir in laid-back Sonoma, and save a morning for the towering coast redwoods of Muir Woods, where parking or shuttle reservations are required, or swap in the cliffs and beaches of Half Moon Bay. The city itself rewards slow wandering: dim sum in Chinatown, espresso in North Beach, murals in the Mission and sunset at Ocean Beach. Pack layers whatever the month, since summer fog can drop temperatures into the 50s while the sun shines a few miles inland, and wear comfortable shoes for the steep hills. September and October usually bring the warmest, clearest days of the year.