NYC and Chicago at Christmas vs Route 66

This holiday lights trip pairs two of America's most festive winter cities: three days in New York, then a short flight to Chicago for two more. In Manhattan, stand beneath the Rockefeller Center Christmas tree as skaters circle the rink below, browse the glass kiosks and free-admission ice rink of Bryant Park's Winter Village and walk Fifth Avenue's elaborate department store windows and light shows. Ride the subway to Brooklyn for Dyker Heights, where homeowners cover entire houses in lights, inflatable Santas and animated nutcrackers. In Chicago, sip hot spiced wine from a boot-shaped mug at the German-style Christkindlmarket in Daley Plaza, stroll the Magnificent Mile beneath trees strung with more than a million lights, skate at the McCormick Tribune Ice Rink in Millennium Park and end at Lincoln Park ZooLights, a glowing, family-friendly tradition. The best window is mid-November to early January: markets generally run from mid-November to Christmas Eve, the Rockefeller tree is lit in early December and most displays stay up into the new year. Visit before December 23 to catch everything open. Pack a warm coat, hat and gloves, because Chicago nights often dip into the 20s, and book hotels early.

Route 66 is the great American road trip: roughly 2,400 miles of the Mother Road from downtown Chicago to the Pacific at Santa Monica, crossing eight states and three time zones. This Chicago to Santa Monica itinerary packs it into 10 days, which is fast. Expect about 200 to 330 miles and five to seven hours behind the wheel most days, mixing interstate stretches with the best surviving original alignments; two to three weeks is ideal if you can spare it. Start with a photo at the Begin sign, then roll past Illinois giants, the bent Chain of Rocks Bridge over the Mississippi and Ozark frozen custard stands. Cross the short Kansas corner and Oklahoma's diners before painting your own stripe at Cadillac Ranch outside Amarillo. In New Mexico, sleep under the glowing neon of the Blue Swallow Motel in Tucumcari, then drive through the badlands of Petrified Forest National Park, the only national park that protects a stretch of Route 66. A day off the road from Williams takes you to the Grand Canyon's South Rim. The finale climbs over the Black Mountains to Oatman, crosses the Mojave and ends with a sunset at the Santa Monica Pier. Book classic motels ahead in spring and fall.