Chicago vs Colorado Rockies

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.

The Colorado Rockies pack big mountain scenery within easy reach of a lively city, which makes them perfect for a long weekend. Start in Denver, the Mile High City, where food halls, breweries and green-chile-smothered everything have turned neighborhoods like RiNo, LoHi and Union Station into a serious food scene. Just 30 minutes west, Red Rocks Amphitheatre sits between towering sandstone slabs and is one of the world's most famous places to see a concert, or simply to climb the stairs at sunrise. From there the mountains take over: Trail Ridge Road in Rocky Mountain National Park climbs past 12,000 feet above treeline, and the old mining towns of Idaho Springs and Georgetown, plus the gateway town of Estes Park, make charming bases. With more time, head to Breckenridge, Vail, Glenwood Springs' hot springs pools, Aspen's Maroon Bells and the red rocks of Garden of the Gods near Colorado Springs. Plan ahead: Rocky Mountain National Park requires timed-entry permits in summer and early fall, the Maroon Bells need a shuttle or parking reservation, and the altitude is real, so drink plenty of water and take the first day easy.