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Skate under the Chicago skyline and within eyeshot of the Chicago Christmas Tree at the McCormick Tribune Ice Rink in Millennium Park. Admission to the rink is free, and you can rent skates for $13–$15. Plus, take advantage of free skating lessons on most Saturdays and Sundays from 8am–9am, where you can learn both beginner- and intermediate-level skills. Note that you'll need to make a free online reservation for both regular skating and lessons this year, and if it seems too warm to skate, call ahead—this rink is open through March 6, weather permitting.