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When it comes to places with flowing hills and towering mountains, Chicago IL never tops the list. In fact, this city is the second flattest in the country. However, in winter, with snow falling and children eager to try out sleds, tubes, and toboggans, the city does not disappoint. In fact, it has several hills, both legal and illegal, challenging, and perfect for younger children. So bundle up and seek out the hill that suits your skill and/or thrill level. The list provided below can help.

The Best Sledding Hills

When it comes time to hit the sledding slopes, Chicago offers a good selection considering its reputation for flatness. While none of the hills are monumental, they do offer variety and enough to keep most children happy.

A. Montgomery Ward Park: This hill, in River North and situated on the banks of the Chicago River, is small and suitable for children. Even toddlers can have fun while getting a chance to show their independence since the height of the hill does not require parents accompany them to the top. Although the slope leads down to the river’s edge, the fence prevents any further incursion.

Caldwell WoodsWhile Caldwell was once known for its established toboggan run, those days are gone. The tracks were removed by Cook County. Yet, they could not take away the hill. Today, you can still join those who choose to make their way here, sometimes choosing afterwards to stray to nearby legendary SuperDawg for a hot chocolate afterward.

Cricket Hill: This is a true hill. Making your way to the top may take time, but the view alone is worth it. You can look down at the lakefront before deciding which of the four-sides you plan to slide down.

Dan Ryan Woods: This steep hillside, popular for snow-related sports since before the 1930s formalized them here, stretches upwards for 400-feet. However, it is not a chore to get to the top. The exercise stares located beside the slope make it easier. Lighting also provides that extra safety as you approach this experience with a little more frisson than you might other Chicago hills.

Humboldt (Alexander) Park: This Park is known more for its free ice skating. However, the hill on its own it is more than adequate for a fun time.

Palmisano (Henry) Park: Once a quarry, this Park continues to boast a remarkable hill. Fondly known as “Mount Bridgeport,” it offers great views of the city’s skyline and a fast track down.

Soldier Field: At 30-33 feet in height and with a drop of some 220 feet, this sledding hill is tall and fast if not long. It is also consistently covered thanks to the snowmaking machines used by the Chicago Park District. Like most tall hills in Chicago, you can see some of the city’s sights, including the Stadium and Lake Michigan.

Warren Park: Created in the 1970s, this park features stairs with railings flanking both sides. It is steep and, therefore, a favorite of larger children and their toboggans. You can also go ice skating on the highly rated, outdoors, Chicago Blackhawks Ice Rink and/or spend time warming up at a warming house nearby.

Sledding in Chicago

While Chicago IL is not blessed with copious hills, it still offers children and adults the chance to go sledding. While some hills are clearly suitable for young children, others are more challenging. Their existence allows those living in and visiting Chicago to get out and have fun in and on the snow.

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