My daughters are still quite young and I'm really no Michelle Kwan myself, so, for us, what constitutes a great ice rink is the one that is not the coolest, most popular place in town. The ice rink in Millennium park looks so fun but we definitely need a few years practice before we'll be there and the rink at Wrigley just seems too crowded. We've found a couple ice rinks in the City that are less crowded or if they are crowded everyone else is a beginner too.
Midway Plaisance Park (1130 Midway Plaisance North)
Hours: Mon. - Fri. and Sun. 12-7, Sat. 1-9.
The skating rink is located on the University of Chicago's campus but open to the public. We've been here a couple times, once with the girls, and it has never been super crowded. Skating is free during the week but costs $5/person on the weekend. There is a little building where you can rent skates, purchase snacks (coffee, chips, soda, that kind of thing), and warm up a little bit. Skate rental is about $6. Parking is available on Midway Plaisance (going either direction) for free. On the weekends and afternoons it is usually decently easy to find parking - basically anytime you're not fighting with students for spots. Driving is your best bet, since taking public transportation to Hyde Park can be tricky. They also offer Skating lessons at the park on Saturdays and Sundays.
Warren Park (6601 N. Western)
Hours: Wed.-Sun. 12:30-2:30, 3-5, 5:30-7:30
At the opposite side of the City, Warren Park offers another good place to ice skate. When we went over Winter Break it was pretty crowded but the majority were families with kids who were just learning to skate. Skating is free here if you have your own skates and I believe skate rentals are around $6. This rink also had a little building to warm up in, however they do not sell snacks. The park has a large, free parking lot right by the ice rink. I believe the gaps in skating time is when the ice is cleared of skaters for the Zamboni machine.
American Heartland Ice Arena (7374 N. Lincoln, Lincolnwood)
This skating facility does not currently offer open skating to the public (public skating will resume in the summer) but they do offer plenty of skating lessons. The arena has two skating rinks. The larger, nicer rink is used for hockey leagues and the smaller rink is used for ice skating lessons. They offer a lot of different lesson options depending on skill level for kids starting at 3 years old. Their website provides details on all classes (www.heartlandicearena.com). The tot classes, which my daughter has taken, are 30 minutes long and then they allow the kids 15 minutes afterward for free skate, which you can join your kid for if you have skates. Skate rental for kids in classes is $2. You can watch your child through large windows in a heated room or out in the rink just off the ice (which is quite chilly). My daughter has really enjoyed her classes at this facility. The teachers are super nice and incredibly patient. There is probably about one teacher for every 4 kids for the very basic classes with a lower teacher/child ratio for more advanced classes. Your child doesn't need to have any skating ability to take the introductory class. There is a snack bar with drinks, candy, and other snacks, plenty of room to sit and wait for your child's class to finish, and a large parking lot adjacent to the rink.
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