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There are outdoor ice skating rinks at Millenium Park and Navy Pier. Skate rental at Millenium Park is $7 for unlimited time. Expect a crowd at holiday times and weekends; even on New Years Eve you could wait about 35 minutes.
The Chicago Wolves Hockey Team plays at the Allstate Arena near OHare Airport. It's easy & cheap to get there by CTA: Blue Line towards OHare, get off at Rosemont, transfer to PACE bus which takes you to the Arena. Game tickets are $11 and up. It's very family friendly; fireworks before the game, fan-participation contests on the ice during the breaks, a remote control "blimp" that circles overhead dropping prizes, the costumed mascot "slingshots" t-shirts into the stands. You can't help but have a good time, even if you don't know a thing about hockey.