The best time to sled is as soon as possible after the snow stops, but also when it's warm enough for your kids to last more than two rides down the hill. Some sled hills aren't open unless the snow is at least three inches deep, and many hills don't allow sleds with metal runners.

Parents should check each hill's guidelines before heading out to make sure the hill is open and little ones have the proper gear. Bear in mind that the sun goes down as early as 4:20pm during the darkest days of Chicago's winter, so if you want an after-school run, look for a lighted hill. Also, if you've got littles who won't make it home before they have to go, many parks have restrooms or port-a-potties. Bring a mask in case you have to go indoors.

Fly down the hill at a Chicago-area sledding location.

Best Places to Go Sledding in Chicago's North Side

Warren Park

Head to the far North Side for all kinds of winter fun in the West Ridge neighborhood. Warren Park's sled hill has stairs up both sides for ease of climbing up the hill, and a warming house for little ones when they get cold. Getting tired of sledding? One of the North Side's best skating rinks is also in Warren Park, with skate rental available. Parking is available in a free lot off of Western Avenue. Make it an evening with a pizza at Candlelite, just one mile up Western Avenue.

Horner Park

One of the city's school cross country courses in the fall serves as a great sled hill in the winter within this huge park along the Chicago River in Irving Park. The hill at Horner Park isn't super-steep, making it fun for kids of all ages. A playground provides additional entertainment during less snowy days, and a field house in the park gives kids a chance to warm up during Chicago's coldest times. Parking is easy in perpendicular spots along the park's west side. Stop by Lutz Bakery near Western and Montrose for a sweet treat afterward.

Cricket Hill

Anyone who has traversed the Lakeshore Trail has recognized its great potential. With views of the lake, a restroom, and convenient parking, Cricket Hill has a steep slope best for bigger sledders. The hill can be crowded at peak sledding times, so families should prepare a backup plan in case the hill is too packed for little kids. 

Humboldt Park

It's been more than three years since Chicago's resident alligator Chance the Snapper vacated his premises at Humboldt Park Lagoon, but the park's sled hills are still perfect for little sliders. The hill west of the field house is small and best for little kids, allowing West Side families to get their sledding fix without driving too far. Free ice skating is also available, and families can enjoy food trucks that frequently come by. Street parking is available in surrounding neighborhoods and might be easier on the streets on the park's northwest side. If you're not packing huge sleds, taking the Blue Line to Damen is also an option.

 
Caldwell Woods is ideal for sledders of all ages. Photo courtesy of the Forest Preserve District of Cook County

Caldwell Woods

Cook County Forest Preserve's Caldwell Woods offers sledding with lights from 10am to 7:30pm on school nights and 10am to 8:30pm on weekends. This former toboggan run has enough slope for a fast ride, but can still be appropriate for younger sledders. Indoor bathrooms and a fire pit near the warming center make this a great place for kids who can't stand the cold for very long.

A free parking lot is located at the southwest corner of the park. And a certain dad in this house would be upset if we didn't mention that it's right down the street from Superdawg, one of the city's most beloved hot dog stands, where eating in your car is a must.

Best Places to Sled in Downtown Chicago and the South Side

Dan Ryan Woods

This giant forest preserve in the Beverly neighborhood is rarely crowded and offers opportunities for both sledding and snowboarding. The facility is lighted until 7:30pm on weekdays and 8:30pm on weekends. The 200-foot hill has great views of the Chicago skyline above the surrounding forest and easy paths up the hill for little ones. There are several free parking lots within the forest preserve. The Cook County Forest Preserve District requires 3 inches of snow for the hill to be open, so families should call ahead to make sure there's enough powder to sled.

Palmisano Park

The former landfill known as Mount Bridgeport is a thrilling sled ride for Downtown and Near South Side families. The park also has a hiking trail and pond for scenic enjoyment when families want a break from sledding. Parking in the neighborhood can be tight on good sledding days, but the 8 Halsted or 62 Archer buses are an option if you have a small sled. Nearby Bridgeport Coffee offers warm beverages to heat cold bodies at the end of the sled ride.

Soldier Field

Bears season is over, and on a nongame day the 33-foot hill near the stadium's south parking lot (which should be easy to park in on nongame days) is a landmark sled hill for Chicago kids. The Chicago Park District makes its own snow as long as the weather is cold enough, so kids can stop by during most of Chicago's freezing winter. This could be a fun supplement for a trip to the Field or the Shedd Aquarium. Only plastic sleds are allowed on the hill and it is not supervised by the park district, so parents should ensure their littlest sledders remain safe.

Best Places to Sled with Kids in Chicago's North Suburbs

James Park—Evanston

Parents who grew up on the Far North Side or Near North suburbs might remember the 65-foot landfill known as Mount Trashmore for its thrilling sledding. While the city of Evanston now prohibits skiing and sledding on the mount itself, four small and medium-sized slopes surrounding it in James Park provide sledding fun for kids of all ages. A small parking lot is available on the park's south side. 

Caboose Park—Lake Villa

One of the area's last remaining toboggan hills is in this far northern suburb. The park is lit from 5:30pm to 10 pm each evening, and the parking lot offers easy access for families driving in from other suburbs. 

Techny Park and Field—Northbrook

This 28-foot North Suburban hill has stairs to make getting your sled up to the top easier, as well as lights for evening sledding and a warming house to heat little fingers and toes. The park also includes a prairie landscape with trails, playground, and a skatepark in case kids need a break or don't have enough snow to sled. Several parking lots line the south and west sides of the park. Downtown Northbrook isn't far away for sledders looking for a meal or warm drink after some thrilling sledding.

Flick Park—Glenview

With convenient parking and lights for night sledding, this Glenview park is perfect for a low-key sledding trip. The Glenview Park District doesn't open the hill until it believes the snow is deep enough for sledding, so make sure you check the website before heading out. Flick Park also has a skating rink for a change of pace. Families can park their cars near the Flick Park Aquatic Center.

Eldridge Park in Elmhurst boasts sledding hills and more. Photo courtesy of the Elmhurst Park District

Best Sledding Hills for Kids in Chicago's West Suburbs

Eldridge Park—Elmhurst

This large park in the near Western Suburbs has a lighted sledding hill with paths on each side to help kids haul their sleds back up the hill. The park also includes a lagoon for skating or watching ducks, and a trail that connects to the Salt Creek Greenway Path. Parking is available on the park's east side or in nearby neighborhoods. 

Rotary Hill—Naperville

This lighted hill is adjacent to Naperville's Riverwalk. Fenced walkways along the side help kids get their sleds back up the hill. On a non-school day, families can park across the street at Naperville Central High School, or find street or garage parking in the downtown area. Sledders have no problem making a day out of the trip: Naperville's downtown has plenty of fun places to eat or grab a hot chocolate, including an outpost of JoJo's Shake Bar.

Northside Park—Wheaton

At one of the few suburban parks that still allows toboggans, kids can ride down this not-too-steep hill in Wheaton. The park also has a pond for skating (when it's cold enough) and a warming shelter for taking breaks from the cold. Parking is available in lots near the south and east sides of the park. Make a day of it by visiting nearby Cosley Zoo, a favorite for young west suburban kids.

Barrie Park—Oak Park

When the Park District of Oak Park remediated Barrie Park from 2000 to 2005, they designed and built a sled hill for west side and near west Suburban kids to slide down. The design is not too steep of a slope, but has a fast slide that may have little kids requesting a grown-up ride-along. The hill has stairs to help kids get back to the top, and park amenities include lights, restrooms, and a playground. Park on neighborhood streets or take the Blue Line to Austin to get to Barrie Park.

Blackwell Forest Preserve—Warrenville

This massive far west suburban forest preserve has snow tubes and snowshoes available for rent when the snow is 3 inches or deeper. For just $10 a day, kids can whiz down Mount Hoy. Tons of trails also give families the chance to snowshoe, cross-country ski, ride horses, hike, or even ride a dog sled. Ice fishing is also allowed. Parking is plentiful throughout the preserve so families can easily get back to their warm car from plenty of different winter fun activities.

Best Places to Sled with Kids in Chicago's South Suburbs

Pioneer Woods—Near Willow Springs

The Forest Preserve District of Cook County maintains this unlit hill in the unincorporated area near Willow Springs. Portable bathrooms and picnic shelters are located nearby. The hill is also near the Palos Trail system, so families can hike, bike, or cross-country ski to other preserves to explore a little more of the South Suburbs' nature. A parking lot provides access to the woods and trail system along 107th Street just east of 104th Avenue. 

Kasey Meadow Park—Hickory Hills

This South Suburban sled hill has stairs and lights to help little sledders get up and down safely. The park features easy parking, a recreation building with bathrooms, and a half-mile walking trail. The Cynthia Neal Center at the top of the hill has hot chocolate available. Metal sled runners are not allowed on the Kasey Meadow Park sled hill. 

James J. Sexton Park—Evergreen Park

Just south of the city, this park offers more than just sledding. Before or after hitting the slope, visit the dog park, educational agricultural farm, or disc golf course. The park's name was recently changed from 50-Acre Park, and it has more than 50 acres of recreational green space. Access the parking lot from 91st Street just west of Rockwell.

Unless noted, photos courtesy of the park districts