Hit the Slopes in Wilmot Mountain in Wisconsin

Pack your snow gear and head about an hour north of Chicago to Wilmot Mountain for snowboarding, skiing and tubing. Wilmot has been in operation since 1938, but with their recent facelift, skiers and boarders can now enjoy updated towers and chairs, rope tows, an expanded terrain park, beginner area conveyor lifts, new decor in the base lodge and improved dining options. 

Find a Cozy Cabin

We're knee-deep into the cold-weather months and most of Chicago is sticking close to home due to COVID-related uncertainty. For a change of scenery or maybe even a quick getaway without the kids, escape to a sweet cabin in the woods. Within a short drive, you'll find cozy cabins, sweet cottages and even a converted grain bin to unplug and schedule time amongst the trees and alongside lakes. Relax, unwind and say hey to Mother Nature. Find your retreat here. 

Check Out Galena

Beat the winter blues and CELEBRATE winter with a trip to charming Galena, where gorgeous rolling hills blanketed in snow (if it ever falls, that is!) surround a quaint, history-filled small town. While Galena is a wonderful city to visit year-round, wintertime promises magical, hygge-filled experiences. They have special COVID procedures in place to keep visitors as safe as possible and the activities encourage staying outdoors. Read more about Galena here. 

See Eagles at Starved Rock State Park

Winter, spring, summer or fall, all you have to do is haul your crew to Starved Rock State Park for hiking with a stellar view. Starting in mid-January, thousands of eagles migrate to Starved Rock State Park and stay through March. They’re easy to spot as they soar through the sky or perch on the treetops. Bring binoculars!

Hit the Highway for a Little Escape

Kids dig hotel stays for the chance to sprint down long hallways and jump like monkeys on the bed. Parents love vacay for the squad-bonding opportunity, replacing the same ole for a new scene and having someone else make the bed for a change. Take a winter road-trip escape to destinations that allow for time in the great outdoors and lots of space to socially distance as a family.

Take the Family for a Spin at Maggie Daley

The Maggie Daley Park ice skating ribbon is one of the best spots in the city to skate a figure eight. The railing that lines the loop is the perfect pick-me-up for wobbly skaters. 

Bundle Up for a Wintry Hike

We’ll admit, a Chicago winter can be brutal. But, a dose of fresh air, unforgettable scenery and a chance to visit animals in their natural habitat is a guaranteed day of wintry family fun. There are beautiful trails all around the city that'll have you lacing up your boots, strapping an infant to your back and setting out for an adventure. 

Have a Scavenger-Hunting Adventure

Show your kids the coolness of their hometown with a scavenger hunt. You'll spy on Navy Pier's Ferris Wheel and stroll along the Chicago River to see its moveable bridges. Best part? You can do all this in a totally safe, socially distanced way that’ll keep Covid-19 far, far away. Mask up and hop in the car to seek out these Insta-worthy Chicago landmarks. You can download our Chicago-themed scavenger hunt for kids here.

Take a Walkie-Talkie Neighborhood Tour

Chicago Children's Theatre got creative during COVID shutdowns! They commissioned fun, totally original audio experiences that facilitate families exploring Chicago neighborhoods called Walkie Talkies. Take a self-guided tour through South Shore, Little Village and around the North Pond Nature Sanctuary in Lincoln Park. Even during the winter months, you can be outside learning about our beautiful city.

Lace Up the Skates at The Forge

It wouldn't be a midwest winter without ice skating on the to-do menu. Lace-up your skates—or rent a pair—and glide across The Forge's Ice Skating Shelf. Teleport yourself to childhood memories and create new moments to cherish.

Find a New Favorite Neighborhood Toy Store

We all know the last year has been rough on small businesses. While Christmas is behind us, perhaps you have a birthday coming up? Or, are treating the kids to a just-because gift? Make your kid's toy-filled dreams come true at a locally owned toy store. 

Hunt for Chicago's Best Cup of Hot Cocoa

Make Chicago's winter a little easier to swallow with a steaming cup of hot chocolate. When Jack Frost comes nipping at your nose, it’s time to go sipping. If your kids love cocoa—or need a good introduction to it—check out local restaurants or cafes that make their own from scratch. 

Intro Your Kids to a Chicago Hot Dog

Love ’em or leave ’em, hot dogs are big in Chicago, and if your kids haven’t begged for one yet, they will soon. We love the on-the-go ease (no silverware!) and colorful condiments (kids get a pass where the sacrilege of using ketchup is concerned). Grab one at a legendary local hot dog spot and turn eating into an adventure. 

Fill Your Bellies with a Hearty Bowl of Soup

Slurp it. Stir it. Make waves. Blow on it. Nibble the good stuff and use a straw for the rest. No wonder kids love soup; it’s so fun to eat. And it keeps us warm and cozy, which right now is a very good thing. From a Jewish deli with great Matzah balls to an Argyle Street pho haven, we'll help you get your fix by sharing our favorite Chicago restaurants for soup. 

See Chicago Children's Theater's Frederick

Frederick is Chicago Children's Theatre's first venture into releasing online content for families via their YouTube channel, CCTv. The award-winning picture book comes to life as a clever and colorful virtual puppet show.

It's the simple tale of a family of field mice who work together to prep for the long, cold winter. Although the work is difficult, all the mice but Frederick realize if they pull their weight, they'll be ready. The other mice think he is lazy and daydreaming his days away. But when winter arrives, it’s Frederick who has a special surprise that helps them survive until spring dawns again.

Book a Virtual Playdate with Storytown Improv

Plan a virtual playdate for the kids with the help of Storytown Improv. While Storytown has halted their family-favorite in-person performances, they are using the same tools that have made their Saturday performances a success to host virtual laugh sessions. Choose between an Improv Workshop Party that introduces kids to the basics of improvisation or an Interactive Performance Party with 3 performers and a musician who are ready to take kids on any adventure they can imagine. 

Tune into "What Will She Do Next?"

What Will She Do Next? is a musical podcast for kids that celebrates key moments in the lives of history's greatest women. The educational and entertaining series also features bite-sized biographies with no singing or actors that are perfect for bedtime. The podcast can be streamed free of charge on whatwillshedo.com, Apple, Spotify, iHeartRadio or anywhere you get your podcasts.

Shake your Groove Thing with Mr. Dave's Music

Mr. Dave guides kids through a virtual 30-minute musical experience designed to keep them engaged, active and happy. Your musical adventure will feature the greatest kids hits, storytelling and imagination play, creative thinking and oral language development. They'll also be introduced to new sounds and instruments from all over the world.