10 Winter Outings To Do With Your Family

Winter in Chicago can be a bit dreary but is also a great time to try some new experiences together as a family. We like to make a bucket list of fun family outings in the winter and forge new family memories. Our kids are getting older and more adventurous so we love trying new outings together to keep that family bond strong. Sharing 10 fun winter outings to do with your family around Chicago and in Wisconsin.

Snow Tubing in Wisconsin

Pack the car with your snow gear (maybe even a dry change of clothes) and snacks and head to Wisconsin for a fun day outside for the whole family. Some of our favorite places to go tubing are Wilmot, Cascade Mountain and Sunburst Winter Sports Park.

• Wilmot ~ 1-1.5 hours from Chicago just over the Wisconsin border. Epic recently bought Wilmot and made some “epic enhancements”.
  • Price: $33 for a 2-hour session during the weekends and holidays. You’re paying for the convenience.
  • TIP: Pack a lunch and snacks to save some money.
• Cascade Mountain ~ 2.5 hours from Chicago, near Baraboo Wisconsin. We did a day trip to Cascade Mountain for Mike’s birthday and stopped for dinner in Madison – a long day but one that we still talk about.
  • Price: $27 for unlimited tubing ($15 for the last 5 hours). Good deal if you want to tube, take a lunch and hot cocoa break and tube again.
  • TIP: Pack the kids and car, stop at Starbucks and hit the road early. Grab dinner in Madison, WI (~45 min south of Cascade Mountain).
• Sunburst Ski Mountain ~ 2+ hours from Chicago and 50 minutes north of Milwaukee. Over 45 tubing lanes which make Sunburst the world’s largest tubing park. We combined tubing with a stay at the Osthoff Resort for a super fun family winter weekend.
  • Price: $18 for a 2-hour session during the weekends & holidays, $15 if you book in advance. Definitely the best value.
  • TIP: Book in advance to save $3/ticket. Consider staying a night at the Osthoff (~40 minutes away) or stopping in Milwaukee for dinner.
• Rock Snow Park ~ Just over an hour from Chicago. We have not been here but it’s on our list. Our kids love the idea of glow tubing (Friday and Saturday from 9-11p).
  • Price: $19 for a 2-hour session during the weekends & holidays
  • TIP: We’ll update once we’ve been there!

Ice Skate at the Skating Ribbon in the Maggie Daley Park in Chicago & Family Dinner

Bundle up and ride the metra or drive downtown to ice skate at the Skating Ribbon in the Maggie Daley Park in the heart of Chicago.

In the heart of downtown Chicago, with the city’s skyline as a backdrop, a ribbon of ice winds through a rolling landscape providing an ice skating experience unlike any other. The skating ribbon is dramatically different from typical civic ice rinks, creating a multisensory activity that is integrated into the landscape

After you’re done skating, stroll through the Maggie Daley Park and stop to play in the Play Garden.  Enjoy a family dinner near Millenium Park at The Gage, Park Grill Chicago or Atwood.

Day at the Museums

When the kids were young, a visit to the museums meant the Kohl’s Children’s Museum in Glenview, IL which they all absolutely loved or the Peggy Notebaert Nature Museum in Chicago, IL during the week to see the butterflies. As they’ve gotten older, we’ve ventured to the Chicago museums – such a great way to expand everyone’s minds and spark interesting family conversations. Sundays seem to be our best bet since the kids’ activities are mostly on Saturdays. We visited the Planetarium last year and kids are still talking about the exhibits. We’re due for an outing to the Field Museum.

TIPS: The Field Museum is free every day in February 2019 for Illinois residents for proof of residence. Click here for more free days. Parking can be expensive, considering checking out Spot Hero. Pack a lunch to avoid a pricey meal and long lines.

Escape Room

Fiona went to an Escape Room and has been begging for the family to go. We’re planning to go when we’re at the Mall of America over President’s Day Weekend. Our good friends went to this Escape Room in Schaumburg with their extended family and raved about it.

Volunteer to Pack Meals at Feed My Starving Children & Grab Dinner Afterwards

We aim to volunteer at Feed My Starving Children twice a year. During our last outing here, we were among 100 other volunteers that packed 76,000 nutritious meals for severely malnourished kids and families. This is a small way our family can give back and be grateful for what we have.

TIPS: The Saturday 4-6p volunteer time slot is our favorite but fills up fast so book in advance. Leave your jewelry & watches at home as you can’t wear it while volunteering.

We like to grab dinner afterward and have quite meaningful dinner conversations. O’Toole’s Libertyville is our favorite spot.

Indoor WaterPark

Sometimes you need a glimpse of summer fun in the winter and what a better way than a pool day at an indoor water park. Here are some options:

• The Water Works in Schaumburg, IL – nonresident rates are $8/youth and $10/adults.
• Splash Landings Aquatic Center in Glenview, IL – nonresident rates are $7/days. Grab lunch at The Glen afterward!
• TimberRidge Waterpark in Lake Geneva, WI – offer daycation packages for $99 which includes 5 water park passes and a one-bedroom suite from 12p-11p. The catch is that this is available Monday – Thursday, so an option for teacher in-service days

Stay Overnight at a Hotel

Cabin fever can be a real thing during the winter. Sometimes you just need to get away – even just for a night. We love to pack up and get away to the Grand Geneva Resort or the Osthoff Resort. Love the feeling of walking into the lobby of a hotel, the kids racing down the hallways looking for the game room and pool, sipping a cocktail in the lobby and savoring quality family time.

Visit the Morton Arboretum on a “warmer” winter night

We have an annual tradition to kick off the holiday season with a fun family date night to Illumination: Tree Lights at the Morton Arboretum.   Bundle up, stop for hot cocoa along the walk and be amazed by the beautiful lights at the Morton Arboretum (~ 35 minutes west of Chicago). There’s just something about being outside on a crisp night that can be so refreshing.

We stopped for dinner at La Barra  on our last visit. Everyone enjoyed the cozy booth and delic Italian food.

Go to a College Basketball Game

Can’t beat the excitement of a college basketball game. We saw a Chicago Bulls game a few years ago when Dwayne Wade and Jimmy Butler were still on the team. Planning to root for Marquette at the new Fiserv Forum in Milwaukee during this season. Check out the local Chicago teams – Northwestern Wildcats, Loyola Ramblers, DePaul Blue Demons, UIC Flames.

A Cozy Night at Home to Make Dinner Together and Watch a Movie or Play Boardgames

How good does a family night at home at the end of a busy week sound? Although they’re rare, I love when we’re all working together in the kitchen. Already looking forward to a cozy night when we make dinner together and watch a fun family movie – possibly, Miracle? Another idea is to play board games in the living room by the fire.

What are some of your favorite family outings during the winter?

Happy Travels,

Bridget, Family Galavant