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Chicago's Best Sled Hills

F & P - Guide to Sled Hills in Chicago - 12.23.11 - Face Plant-Kenaz-Mara
(credit: Bonnie Kenaz-Mara)

by Bonnie Kenaz-Mara

I came of age in hilly, Midwestern Cincinnati, where the glaciers that flattened Illinois finally melted, resulting in some serious sled hills. Kids from the whole neighborhood descended on our back yard, to sled our little hill. When we got older and more adventurous, we trekked across the street to the golf course, for higher thrills. So, it came as somewhat of a surprise to me, to find myself raising children in the flatlands, where sledding isn't just out the back door.

The most serious sled hill in the region is Evanston's infamous, Mt. Trashmore, an illegal yet still wildly popular sledding destination built up from landfill at a former dump. We'll stick to the ones where sledding is actually encouraged. A day of sledding in Chi-Town requires some planning and usually entails loading up the car and making a drive. Still, we've discovered some gems over the years. Here are our favorites. Sled hills are generally unstaffed and it's sled at your own risk. Parks are open from dawn until dusk, unless otherwise noted. Admission is free.

F & P - Guide to Sled Hills in Chicago
(credit: Bonnie Kenaz-Mara)

This picturesque little hill on the lakefront is our favorite for atmosphere. The view from the top is sweet, with the urban cityscape to the west and the open lakefront to the east. You can also slide down all sides, minimizing wait time. The downside is winds can be brutal and temperatures lower by the lake, and there are no close restrooms or indoor warming space. The upside is you can bring your dog along. The north end of Montrose Beach has an awesome dog park (city dog park permit needed) and leashed pooches are often seen around Cricket Hill, sledding with their families. You may also want to check our guide to pet-friendly dog parks.

Sledding Sled!
(credit: Bonnie Kenaz-Mara)

Warren Park has a great neighborhood flavor and isn't as packed as Soldier Field. The hill here is sizable, and one of the best for toboggans. If you tire of sledding and need a change of pace, this park also has one of the city's best outdoor ice rinks.

Guide to Sled Hills in Chicago
(credit: Bonnie Kenaz-Mara

This hill used to boast a magnificent toboggan run, but in 2008, the cash strapped city couldn't maintain the insurance on it and tore the structure down. For young children, there is still a medium sized hill that's fairly wide, allowing for short wait times. The downside is, the area frequently floods as snows melt, and turns into a mud pit. If the weather is warming, Caldwell hill will likely be roped off with caution tape. The best feature of this sled hill is a sizable warming center with a wood fire pit and indoor bathrooms! You can bring your own s'mores and roast them right there. Thermoses of coffee and hot chocolate and even a winter picnic are a welcome addition to a day of sledding.

Guide to Sled Hills in Chicago
(credit: Bonnie Kenaz-Mara)

Chicago's only major, 33' high, sledding hill was part of Soldier Field's park renovations, a few years back. It's located to the southeast of the stadium. With a 220 foot slope, tow rope and snow machines to pick up the slack for mother nature, this is the hill to conquer. Try to pick off days and times or be prepared for crowds.

Bonnie Kenaz-Mara explores adventures in urban-odd ball-off the wall-alternative-eco-punk parenting in Chi, IL. at
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