
Destination Comparison
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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.
Full Travel Guide
Two of the South's most beautiful old cities sit just two hours apart, making them an easy pairing for a four- or five-day trip. Start in Savannah, Georgia, where 22 leafy squares shaded by Spanish moss-draped oaks break up a historic district made for wandering. Stroll to the white fountain in Forsyth Park, tour a historic house that tells the full story of the enslaved people who lived there, and end the day on cobblestoned River Street watching container ships glide past. Then drive about 110 miles up the coast to Charleston, South Carolina. Walk past the pastel facades of Rainbow Row and the grand homes on the Battery, cool off at the Pineapple Fountain in Waterfront Park, and dig into lowcountry seafood: shrimp and grits, she-crab soup and fresh oysters. Plantation tours such as Magnolia, Boone Hall and McLeod Plantation are part of any visit, and the best of them center the histories of enslaved people and the Gullah Geechee culture they built. With extra days, add Sullivan's Island, the beaches of Tybee Island and Kiawah, and the quiet waterfront town of Beaufort. Spring and fall bring mild weather, blooming azaleas and comfortable walking.
Full Travel Guide| Factor | NYC and Chicago at Christmas | Savannah and Charleston |
|---|---|---|
| Budget / Day | $300-500 USD | $220-400 USD |
| Best Season | Mid-November to early January. Christkindlmarket and Bryant Park's shops run from about mid-November through late December, and most light displays stay up into early January. | March to May for azaleas and highs in the 70s-80s°F, and October to November for warm, drier days and fewer crowds. |
| Known For | Christmas lights, Holiday markets, Ice skating | Historic architecture, Southern food, Lowcountry seafood |
| Local Cuisine | New York pizza by the slice, Bagels, Roasted chestnuts | Shrimp and grits, She-crab soup, Lowcountry boil |
| Getting Around | In New York, ride the subway with OMNY tap-to-pay (approx. $3 per ride, with weekly fare capping) and walk Midtown's holiday sights | Both historic districts are compact and best explored on foot. A car is the easiest way to drive between cities (about 110 miles, roughly 2 hours via I-95 and US-17) and to reach plantations and beaches. Savannah has a free downtown DOT shuttle and ferry |
| Safety | generally safe | generally safe |
AI-Assisted Comparison
Figures and recommendations above are generated with AI from destination data and may change over time. Always verify prices, seasons, and travel requirements with official sources before booking.
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