Spectacular and Free Sledding Spots in Chicagoland

Nothing says winter like racing down a bumpy hill covered in ice and snow while screaming for dear life and watching your life flash before your eyes…am I right?  So be sure to grab a sturdy sled, extra layers, and the warmest pants you have before heading out to these spectacular and free sledding hills in Chicagoland:

Chicago: Caldwell Woods

Why we love it: There is an adjacent warming center and a fire pit to thaw your frozen fingers while talking about your fun trips down the hill. This was my absolute FAVORITE hill as a kiddo in all of Chicagoland.


Chicago: Dan Ryan Woods

Why we love it: It is a hidden gem that is hardly ever crowded and accessible for even the wee ones.


Chicago: Horner Park

Why we love it: One of the biggest parks on the north side, there is lots of room and many sledding hills to choose from.


Chicago: Humboldt Park

Why we love it: When you get bored of sledding, lace up some skates and enjoy the outdoor ice rink. You can also head over to the free Garfield Park Conservatory to thaw as well.

Chicago: Soldier Field

Why we love it: This hill is only for the biggest and bravest of Bears fans. The Chicago Park District keeps snow maintained throughout the winter even if mother nature isn’t cooperating to create a thrilling drop of over 30 feet.  That makes this mama way too nervous, but I’m sure dads around the city would absolutely love it.


Chicago: Ward Park

Why we love it: It is the perfect place to take your toddler to learn the ins and outs of sledding…and for them to gain independence going up and down the hill so that you get a well deserved break.


Chicago: Warren Park

Why we love it: Ample parking, a warming house, stairs, and a starting gate at the top of the slide make this sledding spot very family—and parent—friendly.


Evanston: James Park—Mount “Trashmore”

Why we love it: This old garbage dump provides endless entertainment in the winter, but be sure to avoid the steep off limits areas.


Glenview: Flick Park

Why we love it: Ample parking, clear ramp up to the top of the hill, and a steep slope for daring thrill seekers.


Northbrook: Techny Prairie Park and Fields

Why we love it: We spend our summers playing at this park and on these baseball and soccer fields, so my boys have a blast seeing one of our favorite places all covered in snow.  I love the family friendly elements including lights, stairs, and a warming center nearby.


Park Ridge: Maine Park Bunny Hill

Why we love it: This is the perfect spot for preschoolers and toddlers to have fun sledding without worrying about the big kids trampling them.


Rolling Meadows: North Salk Park

Why we love it: This very family friendly hill is perfect for those just learning how to sled and there are many safety precautions with flags to indicate weather conditions, lights, and cleared stairways to the top of the hill.


Vernon Hills: Century Park

Why we love it: There is an adjacent warming center to thaw when taking a break between sledding runs.


Where is your favorite place to go sledding?  Would you rather go ice skating?  Then be sure to check out this article about my favorite rinks, as well as my Winter Survival Guide.

Happy Sledding!
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  1. Robin (Masshole Mommy) says

    My kids are looking forward to getting out and playing in the snow this year. We just need to get some first 🙂

  2. Elizabeth O. says

    That’s pretty awesome! I love taking my girls sledding when they were little. Would be nice to do it again if we ever drop by Chicago.

  3. Annemarie LeBlanc says

    My kids loved sledding when they were young. Now it is time for the grandchildren and the young nephews and nieces to have fun in the snow. We do not live any where close to Chicago, but we will definitely be enjoying sledding right here where we live.

  4. tina says

    Great blog! I wish we had more places around here for sledding. Most places you need to pay for. You’re inspired me to look for some free places in my area! Enjoy winter!!

  5. Practical Mama says

    We love Schiller Woods and Gompers Park. I need to try Caldwell Woods. That warming center and fire pit sounds so enticing. My kids can sled by themselves and don’t need us anymore. So we freeze, just waiting for them in the cold.

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