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Chicagoland Family Winter Bucket List

By Emily Savage


We tapped our amazing Chicagoland BCB Market Leaders, Lindsay Kaplan, Jill Badlotto, and Jacqueline Baird to help put together an awesome Top Family Winter Bucket List of hot spots, hidden gems & fun things to do with your kiddos during this holiday season and as we head into the cold winter!  We have our Chicagoland community covered from the city to the Northshore to the Western burbs – scroll down to read some of our fave spots not to miss with your kiddos!

Do you have any to add to this list?  Comment below with your fave Chicagoland spots to hit with the fam!

Don’t forget to also keep checking our BCB site for monthly free events here — playdates, workouts + more to help you meet new mamas in your area!  Everyone at these events goes home with goodies from our amazing partner Seventh Generation!


Winter Family Bucket List – Chicago

Toys “R” Us Adventure: There’s nothing better than reliving your childhood with your own children! Just when you thought Toys “R” Us was a fond memory from the past; they’re back with a unique popup experience. You can let your imagination (and kids) run free through a disco castle, safari room, life-size Melissa and Doug toy room, and much more. End the experience upstairs in a massive ball-pit that spans the entire floor!

Teddy Bear Tea at Hotel Zachary: Enjoy a cozy afternoon with you, your children, and their favorite stuffed-animal over high tea! Taking place Saturdays and Sundays from November 30 to December 29 at Hotel Zachary, kids can dine on house-made hot chocolate, tea sandwiches, and yummy sweet treats. And don’t forget to stick around for the special guest storyteller!
Santa at the Shedd: You can meet Santa himself at the Shedd.  This cool experience lets you have a meet-and-greet with Mr Kringle in their private Beluga Overlook area with a professional photog to capture all of the digital cuteness!

Get Crafty at Lillstreet Art Center: Create some holiday crafts at one of Lillstreet Art Center’s upcoming workshops! From pom pom holiday decorations to New Years party favors, your kids are bound to enjoy getting crafty at one of their sessions.
Winterland at Gallagher Way: Don’t let the dropping temperatures keep you inside! Winterland at Gallagher Way has everything you need to enjoy a fun winter day outdoors. Shop the Christkindlmarket and purchase one-of-a-kind ornaments, home goods, accessories, and more for the perfect holiday gift. Enjoy a mulled wine and bratwurst and take a few laps around their ice-skating rink.

Zoo Lights: You can always rely on the Lincoln Park Zoo for a festive time! Make your way there after dark to see the 2.5 million holiday festive lights. December 16, 23, and 30 are family nights where kids can eat free at Park Place Café and all guests can take advantage of unlimited free rides on Lionel Train Adventure and the carousel!
Open Play at Purple Monkey: Sometimes you just need to let the kids run free! Open seasonally from November to May, Purple Monkey is an open floor plan storefront that transforms into a giant playroom, complete with a playhouse, train table, Lego table, slide, dress-up, ride-on toys, and so much more. And you can join us on January 18th for a free BCB play date!
Ice Skate in Millennium Park: Tis the season to bust out your skates! With the beautiful backdrop of downtown Chicago and The Bean, enjoy the 18th season of this iconic winter activity. Skating is free (skates are available to rent) and The Winter Workouts program offers free skating lessons one hour before the rink opens on certain dates.
Visit the Butterflies at the Peggy Notebaert Nature Museum: This is one of the best places to beat cabin fever! It’s forever summer inside the Judy Istock Butterfly Haven, where tropical trees, flowers, and 1,000 butterflies thrive all year long.

Go Sledding in the City: City kids can enjoy sledding, too! All you need is a snow day and a sleigh to enjoy hours of outdoor entertainment at one of your favorite Chicago parks. Oz Park (2021 N. Burling St.), Soldier Field (425 E. McFetridge Dr.), Humboldt Park (1400 N. Sacramento Ave.), and Cricket Hill (601 W. Montrose Dr) all have hills that make the perfect slopes.
Create Art at the Art Institute: Head to the Art Institute of Chicago, one of the city’s best museums, and see classic works of art. Visit the Andy Warhol exhibit (going on through January 26) and then let your kids turn into artists themselves at the drop-in art making workshops. The Artist’s Studio us open for all ages and free with museum admission!

Navy Pier Fireworks: There’s a reason why you see cars stopped on Lakeshore Drive to watch this firework show. Get there early to enjoy the Ferris Wheel and various games and secure a good spot to watch the light show.

Winter Family Bucket List – Northshore

Rainbow Play SystemsMany people do not know that Rainbow Play Systems has open play. For around $10 you can go to their enormous show room and play around on all of their fully assembled swingsets and trampolines. Kids can run, climb, swing, spin and jump all of their energy out! 300 Corporate Woods Hwy, Vernon Hills.

Botanic GardensThere is still plenty to do at the Botanic Gardens in the winter. For one, they have one of the most fabulous holiday lights displays. The Lightscape is a mile long path full of colorful lights with music and to end your night you can roast marshmallows over the fire. You must purchase tickets for this event.
The Deerpath InnBring your children and grandparents to the fabulous Deer Path Inn in Lake Forest. Enjoy a fun and traditional High Tea. Seatings are offered Tuesday- Saturday from 2:30-3:30.
The Polar Express – I know this is big in the city, but up here in the burbs we have a little one as well. You first gather at the metra station in your pjs to a singing choir, hot chocolate and goodies. You then get on the train and ride while singing Christmas songs, have a visit from Mrs. Claus who hands out a jingle bells, the conductor comes in and reads the wonderful Polar Express and then Santa makes an appearance! Lots of fun for all!

Lake County Fairgrounds, Santa’s Rockin’ LightsOne of the most amazing Drive through animated light shows.

The Marriott Theater – The Marriott Theater in Lincolnshire has so many shows for children. They offer great times and prices for families. Shows are typically around one hour, so nothing too long.
ABT –  YES, I’m talking about the electronics store! It’s seriously a free children’s museum. Free chocolate chip cookies for everyone. They even have their own Dylan’s Candy bar inside ABT. They have an area where kids can play with bubbles,  a huge aquarium to look at, constant fountain shows and so much more!
Malls (Northbrook Court and Hawthorn) – with all the open retail space it seems that play spaces are constantly going in. At Northbrook Court, they have Hi-Five Sports, the treehouse and Noggin Builders playspace. At Hawthorn Mall in Vernon Hills, they have Yu Kids Island, indoor ice skating, glo mini golf, a train that goes around the whole upper level and a painting place.

Trampoline Park s– Buffalo Grove Rockin Jump is great because they have toddler only jump times. Sky Zone Vernon Hills is a great venue with lots of different rooms to play in.

Open Gymnastics or Skate times –  Many of the park districts have open gym times and open skate times throughout the winter months and during breaks. Always fun to go for an hour or two and lets the kids run wild on all the equipment.

Greatwolflodge.com – Great Wolf Lodge indoor water park and hotel. Tons of activities for kids and only about 20 minutes away from the North Shore.

Winter Family Bucket List – Chicago Western Suburbs

llumination: Tree Lights at The Morton Arboretum (Lisle) — Be surrounded by color as you walk a one-mile paved path amid interactive lighting effects that highlight the beauty of trees in winter. Enjoy seasonal music, marvel at ever-changing, captivating lighting designs, and warm up by a crackling fire with a cozy drink or roast marshmallows for s’mores. November 23, 2019–January 5, 2020. First Entry: 4:30 p.m. Last Entry: 8:30 p.m. Exhibition Closes: 9:30 p.m.
Cantigny Park (Wheaton) — Brunch with Santa, brunch with the Grinch, Jingle Bell Rock program, and a Lego Train Show are just a few of the family-friendly activities you can enjoy at Cantigny this winter!
Dupage Children’s Museum (Naperville) — Visit one of the Western Suburbs’ favorite places, where play allows kids to make new discoveries, explore new spaces, share experiences, and see themselves and their world in new and exciting ways. It’s the perfect out of the house activity on a cold winter day
Holiday Magic at the Brookfield Zoo (Brookfield) — Now in their 38th year, visit Chicagoland’s largest and longest-running lights festival with over a million twinkling LED lights, a 41-foot-tall talking tree, Chicago Wolves Skating Rink, ice carvers, larger than life LED animal sculptures, zoo chats, and much more!
Waterlemon (La Grange) — Waterlemon is an indoor playspace for children 5 & younger, a gift + clothing boutique, coffee bar, and on the weekends, they’re a party venue! This family-owned and operated business was built with love from the ground up and it’s a must visit with your kiddos this winter.
Shadow Puppet Story Time at Wonder Works (Oak Park) — An exciting adventure into story and legend with Bill, the museum’s story time expert, and his trusty sidekick, who put on an amazingly shadowy performance. Ongoing (Every Monday at 11 a.m. and Friday at 11:30 a.m.).
Parkway Bank Park (Rosemont) — The courtyard of this entertainment district is transformed into an NHL-sized rink adorned with hundreds of twinkling lights. Skate with characters in December with their weekly “Characters on Ice” program. Some of our favorites include Cinderella, Anna, Kristoff, Batman, Catwoman, Santa and more. Admission: Free. Skate rentals: $8.
Ultimate Ninjas (Locations in Naperville, Libertyville, and Chicago) — If your kids are swinging from the rafters cooped up in the house, send them to Ultimate Ninjas. Classes are created and taught by actual contestants on the show American Ninja Warrior, with a focus on different obstacles each week. There are Family Open Play sessions at each location so parents can step off the sidelines and onto the course.
Paramount Arts Centre and Theatre (Aurora) — Beauty and the Beast is running through January 19th! One of Disney’s most beloved animated films comes to life on stage with all the enchanted castle characters in a holiday extravaganza that will thrill, entertain and amaze young and old alike. Recommended for ages 5 and older. The Paramount also offers Classic Movie Mondays! Enjoy the classics of modern cinema on the magnificent two-story screen at Paramount Theatre…for the incredibly low price of just $1 per ticket!
Sky Zone (Elmhurst, Aurora, Orland Park, Joliet) — Trampoline sports, foam jump pits, special toddler jump times, and more! Sky Zone is a must visit to cure cabin fever and let your kids burn off some built up winter energy.

We hope you enjoy this round-up of super fun activities and adventures to do with your kiddos in Chicagoland this winter!  Leave us a comment below & let us know what else we should add to the list. 

If you’re an expectant or new parent in the Chicagoland area, please reach out to say & hi click here to see all of the events in your area!  We’re bringing you the BEST baby gear, products, services + safety information across ALL of our local and nationwide events – Gearapalooza, webinars, playdates + more!  

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