Chicago vs Seattle and Portland

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 Pacific Northwest's most likable cities sit just three hours apart, framed by volcanoes, evergreen forests and waterfalls, which makes Seattle and Portland a natural pairing. Start in Seattle at Pike Place Market, where fishmongers toss salmon, flower stalls spill onto the cobblestones and the waterfront opens onto Elliott Bay. Ride the 1962 monorail to the Space Needle for views of Puget Sound and, on clear days, the snowy cone of Mount Rainier. Then go see that mountain up close on a day trip to Paradise, where summer wildflower meadows and glaciers line the trails. Board the Amtrak Cascades train or drive about three hours down I-5 to Portland, a city of bridges, bikes and coffee. Lose an hour or three in Powell's City of Books, hike the ferny Wildwood Trail in Forest Park and graze your way through the city's famous food cart pods. Finish in the Columbia River Gorge at Multnomah Falls, which needs a timed permit in summer. Longer trips can add Portland's gardens, the Oregon Coast, Mount Hood and Willamette Valley Pinot Noir. Come July to September for the driest weather, and pack a rain jacket the rest of the year.