3, 2, 1 . . . 2019 has blasted off! Time to get pumped for adventuring and lazing in the new year. Shows that focus on travel and boats, bundling up for snow play and figure 8 making, berry picking and apple munching, toes dipped in watering holes or new experiences — there’s something for every season and interest lined up for the year. Read on for our Editor’s picks for making the most of family time.

photo: Chicago Boat, RV and Strictly Sail Show

Cast a line at the Chicago Boat, RV and Strictly Sail Show where pros teach catch and release techniques with live trout or participate in a sailboat derby, and much more!

photo: Wilmot

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 new towers and chairs, rope tows, an expanded terrain park, beginner area conveyor lifts, new decor in the base lodge and improved dining options at Walt's Tavern. 


Through late February, Camp Zachary is popped-up on the terrace of Hotel Zachary. Overlooking the excitement of Winterland at Gallagher Way, visitors to Camp Zachary can relax on comfy couches and enjoy cozy festive décor with hot toddy’s and fire cauldrons to stay warm. For other ideas on camping in style, read our story Best Glamping Spots Close to Chicago.

photo: Pilsen Community Market

Support a variety of local Latino-owned businesses and entertainers at the Pilsen Community Market, every other Sunday, Nov. 24-Apr. 26. Nearly 100% of the 25+ vendors who encompass the sprawling venue every other week are Latina women who are artists, bakers and produce makers.

photo: Chicago Travel and Adventure Show

Daydream about your next family adventure at the Chicago Travel and Adventure Show, which has plenty for kids: they can try out Segways and Trikkes, catch a ride on a camel or try scuba diving.

photo: Maria Chambers

Take advantage of the snow and learn to carve with the kiddos at Four Lakes Alpine Snowports or load up the sleds and hit one of these hills.

Retire your sock skates in favor of the real thing while the weather's perfect for these outdoor ice skating rinks.

photo: Maria Chambers

Enter a world of play and creation as Filament Theatre's Forts: Build Your Own Adventure transforms the theater into a playspace for children and parents to build new worlds. Using cardboard boxes, sheets, clotheslines and more, families build adventures of their own devising. With theatrical design elements of sound and lights working together to support creative play, families are swept away in the adventure!

Plan a sleepover that will go down as (pre)historic when you Doze with the Dinos at The Field Museum. Explore the exhibits with flashlights and then snuggle up with Sue, the world's most famous T.Rex or the Field Museum's newest resident, Maximo the Titanosaur.

photo: Chula Vista Resort, Wisconsin Dells

It's pretty sweet we have the waterpark capital of the world just a quick skip from Chicago. No need to wait 'til summer to take a dip, as the H2O-focused Wisconsin Dells is hopping all year round. Use our story Dells, Yeah! What to Do in Wisconsin Dells in the Winter to plan a winter getaway.

photo: Raging Waves Aussie Mat rendering

Raging Waves is treating Chicagoans to a brand new experience at their already tricked out waterpark in Summer 2020. They're adding, Aussie Mat Dash, a six-lane mat racing waterslide. Six riders race side-by-side in tunnels to the bottom. With only two such slides installed in the world, the Aussie Mat Dash will be a welcome addition to your summertime fun.

photo: The Breakers

As the temps dip and cabin fever spreads like a virus, you might have an itch to go a bit further than the Dells. We'll help you find resorts that offer beaches, endless sporty activities and even 7-toed cats with just one easy-peasy nonstop flight away in our story Easy Winter Escapes from Chicago.

photo: Dinner with a View

Dinner With A View, a pop-up restaurant and outdoor oasis that recently took Toronto and Montreal by storm, will deliver an exclusive culinary adventure under the stars at Pioneer Court on the Mag Mile for a limited time, Apr. 1-May 10. Attendees will dine in temperature-controlled, clear and frameless geodesic domes, meant to stimulate the senses by marrying an elevated culinary experience with a unique view.

photo: Maria Chambers

Something special has emerged from the woods, meadows and vast open spaces at The Morton Arboretum’s grounds. . . unusual creatures, each made of reclaimed wood and measuring 15- to 20-feet-tall. The mammoth mythical creatures of Troll Hunt, an exhibition on display through the end of summer 2020. Enjoy these guardians of the forest, who are trying to make sense of the human world and make us think about our impacts on the planet.


If you’re feeling brave, walk 4.3 feet into a glass box, otherwise known as Willis Tower's heart pumping attraction The Ledge at Skydeck Chicago. Don’t forget to open your eyes!

Berry-stained fingers and homemade pies are the things memories are made of. Check in on local berry farms to see when their fruits are prime for the pickin'.

photo: Great Wolf Lodge via Maria Chambers

Indoor water parks when it's freezing or splash pads for a cool down and indoor play spaces to combat hibernation or high-voltage playgrounds for outdoor playgroup meet-ups, we promise to keep you in the know on all the ways to keep you moving and smiling in 2020.

Summers are made for later bedtimes and non-stop outdoor family fun. From Memorial Day to Labor Day, keep your eyes locked to the skies to experience Navy Pier's weekly fireworks, every Wednesday and Saturday.

photo: Daniel Popper

Five massive outdoor sculptures created exclusively for The Morton Arboretum by artist Daniel Popper will rise above its natural landscapes when the new Human+Nature exhibition opens on Jun. 12. The 20- to 25-foot-tall sculptures will be installed across the 1,700-acre site, where visitors can watch the artistic process over several weeks leading up to the June opening. Using thought-provoking human forms paired with elements of nature, each piece will bring attention to the deep connections between humans and nature.

photo: Chicago Dogs, credit Daniel Boczarski

Very few towns rival the energy our Chi-Town sports team bring to a game. During these days of hibernation, dream about grabbing your cap and soaking up the sun at a (World-Series-winning) Cubs or Sox game. Or, check out a minor league newcomer, the Chicago Dogs. While you wait, hit the UC for a little Blackhawks and Bulls action.

Explore the gardens at Morton Arboretum or simply lounge listening to live music during Thursday Family Nights, June - August. Don't be fooled, though, this is a cool spot to hit every season. From holiday lights to warm days spent getting lost in the Children's maze, it's always a good idea to add Morton Arboretum to the to-do list.

photo: Centennial Beach Naperville

Dream about a perfect Chicago summer dipping your toes in one of our awesome watering holes that are a bit rugged and off the beaten path.

photo: Kidzapalooza

Create a new family tradition of rocking out at Kidzapalooza, the music fest for kids within Lollapalooza. Get inspiration for your own songs as you dance and sing to some of your favorite kindie musicians, and craft your own “masterpieces” at the arts and crafts tables.

photo: Facets

Make plans to attend 37th Annual Chicago International Children's Festival, the largest film festival dedicated to kids, at the end of October. Keep checking their website for updated dates for 2020.

photo: stock

How lucky are we in the midwest that our change of seasons make for the perfect apple growing conditions? Come fall, dust off those wagons and fill 'em with crisp sweetness at one of our many orchards.

photo: Maria Chambers

Make a new family tradition of heading out into the great outdoors and lumberjacking your own Christmas tree. We'll get you started with our story Timber Time: Christmas Tree Farms to Put on Your List.


photo: Christkindlmarket at Gallagher Way

We just closed down Christkindlmarket for the season, but don't forget to keep it on the agenda for next year. Because, it's just that good.

—Maria Chambers


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