Episode #20: Visiting Chicago With Kids: A Family Guide to Winter Fun, Shopping, and Iconic Sights
There is something truly magical about visiting a big city in winter — especially when snow is falling, holiday lights are glowing, and everyone is bundled up in scarves and coats.
This year, we rang in the New Year in Chicago with our five kids, and it ended up being one of our most memorable winter trips yet. From snowball fights downtown to ice skating in Millennium Park, skyline views from Willis Tower, and a shopping day along Michigan Avenue, our three nights in the Windy City were absolutely jam-packed with family fun.
In this episode, I shared exactly what we did, where we stayed, what worked well with kids in winter, and other must-do activities if Chicago is on your family travel bucket list.
Here’s the full recap.
Why Chicago Is Such a Great City for Families
Chicago is the third-largest city in the United States and sits right along Lake Michigan. It’s famous for its architecture, museums, sports teams, and — of course — deep-dish pizza.
A few fun facts your kids might love:
Chicago is home to the world’s first skyscraper
The Chicago River is dyed green every St. Patrick’s Day
Willis Tower was once the tallest building in the world
Deep-dish pizza was invented right here
It’s one of those cities that surprises families with how much there is to do — even in the middle of winter.
Where We Stayed: Residence Inn Downtown Loop
We checked into the Residence Inn Downtown Loop, and it was absolutely perfect for traveling with kids.
Our two-bedroom, two-bathroom suite gave us space to spread out (and avoid bathroom battles), and the central downtown location meant we could walk to many of Chicago’s biggest attractions.
For families visiting Chicago, having a hotel with separate bedrooms and multiple bathrooms makes a huge difference — especially after long sightseeing days.
Arrival Night: Snowflakes, Hot Dogs, and Christmas Lights
After settling in, we bundled up and headed out to explore downtown.
It was the coldest night of the trip, and snow was falling everywhere. The kids immediately started scooping snow off the sidewalks to make snowballs and dropping down to make snow angels right in the middle of the city.
We grabbed authentic Chicago hot dogs from a street vendor — which felt so iconic — and walked over to Millennium Park to see the massive Christmas tree glowing in the snow.
After that, we kept dinner easy with burgers before heading back to the hotel to warm up and rest for the busy days ahead.
New Year’s Eve: Shopping Day on Michigan Avenue
Instead of toys, our kids had been gifted this trip for Christmas — along with spending money to use while we were in Chicago.
So New Year’s Eve became our official shopping day on Michigan Avenue, also known as the Magnificent Mile.
We split up: boys and girls.
I took our two girls to the incredible American Girl Doll Store, which was massive and completely magical. We wandered every floor, picked out dolls and accessories — and yes, I even grabbed one for myself and let my inner child take over.
I had also made reservations at the American Girl Café, which was such a fun experience. The dolls get to sit at the table, the food is adorable, and everything feels fancy and whimsical.
Afterward, we met back up with the boys at the Harry Potter Store, grabbed butterbeer, and relaxed for a bit.
We also popped into the world’s largest Starbucks, which spans four stories and was absolutely packed — but still fun to see. Chicago is also home to one of the largest McDonald’s locations in the world and a massive Apple Store, so it truly feels like a city of big experiences.
For dinner, we had reservations at Ed Debevic’s, a hilarious retro diner where the servers joke with you, dance every hour, and keep the energy high. It was the perfect place to celebrate New Year’s Eve with kids.
That night, we grabbed snacks from 7-Eleven and headed back to the hotel. We had considered bundling up to go to Navy Pier for fireworks, but it was freezing — so we pivoted.
Instead, we watched the fireworks right from our bedroom window.
All five kids stayed awake until midnight — a first for our family — and it was such a special way to ring in the New Year together.
New Year’s Day: Willis Tower and a Slower Afternoon
On New Year’s morning, we headed to Willis Tower Skydeck.
The views were absolutely incredible — full 360-degree panoramas of the city and Lake Michigan.
Then came the glass platforms, known as “The Ledge.” Each group gets about 90 seconds, and it truly feels like you’re floating above Chicago.
We had a professional photo taken of our entire family and snapped individual shots of each kid striking fun poses — such a great souvenir.
Afterward, we returned to the hotel for leftovers and a much-needed rest.
We had planned to visit the Slime Museum or the Museum of Illusions, but after a late night, everyone was wiped out.
So we pivoted.
We watched a movie, relaxed, and reminded ourselves that flexibility is one of the most important parts of traveling with kids.
Lincoln Park Zoo and Family Time
Later that day, we headed to Lincoln Park Zoo to meet up with my husband’s aunt and uncle, who live downtown and volunteer there.
The zoo was still decorated with Christmas lights and holiday displays, making it extra special to walk through in winter.
Because of the cold temperatures, many animals were indoors, but we still managed to see gorillas, monkeys, birds, and lions.
We sipped hot chocolate, enjoyed the lights, and soaked in how unique it felt to visit a zoo in winter.
Afterward, we had dinner with family and got to tour their beautiful downtown home — which was such a cool experience for our kids to see what city living looks like.
Ice Skating, The Bean, and Chicago Pizza
On our final day, we headed back to Millennium Park because the kids had been begging to go ice skating.
We rented skates and walker frames, and the kids had an absolute blast — while I focused on staying upright and avoiding any broken bones.
After skating, we checked out Cloud Gate, better known as “The Bean,” and snapped fun photos of our reflections.
Then it was time for Chicago pizza.
We ate at Pizano’s Pizza & Pasta, ordering both deep-dish and thin crust, and the kids turned it into a competition to see who could get the longest cheese pull.
Other great spots include Giordano’s and Uno’s if you’re looking for alternatives.
After that, we headed back to the hotel, packed up, and made our way to the airport.
Three nights in Chicago — full of snow, skyline views, shopping bags, and unforgettable memories.
Other Must-Do Chicago Activities for Families
If you’re planning your own trip, here are a few more family-friendly favorites to add to your itinerary:
Navy Pier – Ferris wheel, restaurants, and lake views
Field Museum – Dinosaurs and interactive exhibits
Museum of Science and Industry – Hands-on fun for all ages
Shedd Aquarium – Sharks, dolphins, and reef tanks
Adler Planetarium – Space exploration with skyline views
Architecture River Cruise (seasonal) – One of the best ways to see the city
Lakefront paths and beaches in warmer months
Final Thoughts
This Chicago trip reminded us that winter travel can be just as magical as summer.
Snowball fights on sidewalks.
Fireworks from a hotel room.
Cheese-pull competitions.
Slow afternoons after late nights.
Those little moments are often the ones that stick the longest.
If Chicago isn’t already on your family travel bucket list — especially during the holidays — this might be your sign to add it.
Grab my FREE guide to taking your next family trip for nearly free! I’ll show you everything you need to know. If I can do it with a family of 7, so can you!
