9. Chicago, IL
Why you should go: Yes, it’s called “Chiberia” for a reason. But once you get past the cold, it’s the perfect season to get lost in Chicago’s museum culture. Wander the Art Institute of Chicago, the U.S.’s second-largest art museum, The Field Museum of Hatural History, or The International Museum of Surgical Science (which, based on the name alone, might gross you out).
Why it’s a steal: Flights to Chicago are about 24 percent lower than the median airfare for North American flights, and the average fare is $230 between December and March (and as low as $168 in January). And you can save up to 43 percent on hotels in the winter compared to fall, with an average room rate of $184.
Where to stay: The Godfrey Hotel Chicago, in Chicago’s downtown River North neighborhood, has 221 rooms starting at $129 per night. Just as appealing is the indoor-outdoor rooftop where, through February, guests can rent heated, clear-domed igloos for sipping cocktails, roasting s’mores, and taking in panoramic city views.
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