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5 Best Places to Go Sledding Around Chicago

Chicago Sledding PlacesChicago is known for Lake Michigan, the deep-dish pizza, and being notoriously flat.  The flat landscape of our beloved city does bring trouble at times, especially when we’re eager to go sledding.   Even with no topographical diversity, there are some surprisingly good sledding spots around Chicago.  Here are some of the best places to go if you’re in the mood for some toboggan action.  

Oz Park Hill

I might be biased since this was my neighborhood spot growing up, but this hill is Lincoln Park’s best.  

Off of Armitage Ave lies Oz Park, a public green space known for its statues from the Wizard of Oz.  The glorious hill, perfectly round and steep for sledding, is situated just north of the baseball field.  What makes it a good sledding spot is how easily you can traverse it.  Its incline is relatively vertical, but the hill is short, allowing you to jog to the top fairly quickly.  

Getting more rides in is an essential part of a successful sledding experience.  If you live in Lincoln Park, Oz Park is the place to be this winter. https://www.chicagoparkdistrict.com/parks-facilities/oz-park 

Cricket Hill 

Buena Park residents are familiar with Cricket Hill: a large hill with strange folklore regarding the name.  

If you’ve ever traveled up the lakefront path near Wilson Ave, you’ve probably spotted this hill in the distance.  Reaching up to 45 feet tall, it’s the perfect spot for winter fun.  

Many refer to a Chicago Tribune article to explain where “cricket” comes from.  Apparently, Cricket Hill used to be a sinkhole, having swallowed a circus elephant many decades ago.  

Whether you believe that or not, the folklore adds to the magnitude of Cricket Hill’s size.  Head up to Buena Park for your sledding adventure this December.   https://www.chicagoparkdistrict.com/parks-facilities/cricket-hill 

Sled Hill at Warren Park

A little farther north of Buena Park is a monstrous dome aptly known as Sled Hill.

This hill is a beautiful spot for kids, teens, and adults alike.  Railings along the sides add needed safety measures so that everyone can enjoy the racing experience.  Ice skating at the Blackhawk rink is just around the corner when you’re all tuckered out from sledding.  

This Rogers Park hill is a go-to for many northside residents.  Find out more about this park here: https://www.chicagoparkdistrict.com/parks-facilities/warren-laurence-park 

Caldwell Woods 

If you live up in the northwest area of Chicago, you’ve probably been to Caldwell Woods.  It’s a lush, expansive forest that expands into most of Chicago’s northern suburbs.  

Caldwell’s sledding hill begins at the mouth of Chicago’s beloved North Branch Trail.  A couple of feet from the parking lot, an incredibly steep decline forms into the bike trail.  This decline becomes the optimal place for young sledders and their families when covered in snow.  

In snowy and treacherous conditions, park staff is present to ensure everyone is safe and having fun.  Find out more about parking access, trails, and alerts on the Chicago forest preserve website: https://fpdcc.com/places/locations/caldwell-woods/ 

Palmisano Park 

This massive hill is astounding, to say the least.  Known as “Mount Palmisano,” this has to be the tallest hill on the list.  

Driving down Damen Ave to Bridgeport, it’s a sight that’s impossible to miss: a towering, green prominence sticking out from its industrial surroundings.  Once an old garbage dump, this hill is now one of Chicago’s most majestic parks, with a boardwalk overlooking the river.   

Being the tallest hill on this list, Mount Palmisano might not be for everyone.  Younger sledders should take precautions when traversing this urban area.  But if going fast is your motive, this Bridgeport park will deliver.  https://www.chicagoparkdistrict.com/parks-facilities/palmisano-henry-park 

Chicago is far from being a mountainous city, but this hasn’t stopped residents from embarking on sledding adventures.  Both in and around the city, Chicago has many places to offer for fast and kid-friendly sledding.