Top Tips for Winter Trips to Chicago with Kids

chicago with kids

Today we are sharing our top tips for winter trips to Chicago with kids.

We recently returned from a Christmas trip to Chicago. It was definitely something we planned at the last minute!  When we told friends we were going to Chicago at Christmas, they thought we were mad. But honestly, this has been one of my very favourite winter trips EVER.

It started last month, when Flea said, “Let’s go somewhere cold. I want to go ice skating.” 

And so we looked around and found some reasonable flights to Chicago, and found a great deal on rooms at the Four Seasons Chicago via We arrived in Chicago on Dec 19th and flew home four days later, landing on the morning of Christmas Eve.

It was a long flight so we headed straight to the hotel where we caught up on some sleep. We woke early (thanks, jetlag) and spent a couple of hours checking the pages we’d marked in our guide book, and web pages we’d bookmarked showing interesting sights in the city.

The result was a list of about a dozen activities and destinations that we wanted to fit into our five days in the city.

At this stage, I have to say the concierge at the Four Seasons, Karen, was a gift from the Gods. We presented our list, and she instantly set to work, creating an itinerary, identifying where it made sense for us to visit on the same day, and even adding in recommendations of places to eat and drink while we were in different parts of the city. Karen even set to work finding us cinema tickets to see the new Star Wars movie on the release weekend!

Thanks to Karen, we fitted in everything on our itinerary and some extras – and so here is our guide to the 10 things you have to do in Chicago with kids, during a winter trip!

Ice Skating at Millennium Park

top tips for winter trips to Chicago

Millennium Park was a 20-minute walk from our hotel, straight down Magnificent Mile, a long street that’s lined with pretty much every famous store you can think of, and a few you can’t. During the winter, there’s a skating rink here that offers free ice skating. You can hire skates in any size for $12 (there’s no time limit) and there are lockers to store your belongings – you’ll need a dollar in quarters to use them.

Skating here was a real highlight of our trip – although it is 30 years since I last skated and I can report it is most definitely not like riding a bike. It’s entirely possible to forget how to skate, it turns out. I didn’t fall over. But let’s not dwell on how many complete strangers I had to grab on to during our hour-long skating session. But it’s such a fun and supportive environment – everyone was very friendly, and I loved the guy who shouted at me, “Lady, you get better every time you go past me!” 

There were a few bumps and bruises, so put kids in thick clothes would be my advice. Afterwards, you can grab hot chocolate at the warming hut next to the rink, or cross the street to Shake Shack for a reasonable hot lunch.

The Macy’s Christmas Tree

Just a couple of blocks walk from Millennium Park you’ll find Macy’s, where you can pretty much shop to your heart’s content. The store is a national landmark with a Tiffany’s ceiling and the most amazing themed window displays. But while you’re here, be sure to head up to the top floor and scoot through the interiors section to the ‘tree viewing area’.


Macy’s is built around a HUGE nine-storey courtyard and during the holidays, there’s a 50 foot Christmas tree, decorated beautifully. From the top floor, you get an amazing view of the whole tree – and afterwards, if you fancy it, you can even grab a coffee in the cafe at the foot of the tree.

The Christkindl Market

Just a few minutes walk from Macy’s is the famous Chicago Christmas market.

If you’ve ever visited a German Christmas market, then this is effectively a slightly smaller version of that – there are lots of stalls selling crafts, with a focus on food, wooden gifts and decorative items. You’ll also find plenty of food and a (frankly) huge area devoted to gluhwein!

chicago christmas market

It’s absolutely beautiful to wander round and see the lights, and there is a spectacular Christmas tree. At certain times of day, there are carol services and entertainers, too.

When we visited during the day, it was raining and not quite so pretty – but when we went back at night, amidst flurries of snow, it was beautiful but RAMMED – you literally couldn’t see any of the stalls, because there were so many people. So if you’re in Chicago with kids, my advice would be to visit during the day, when you’ll get to see a lot more.

The Art Institute of Chicago

art institute of chicago

If you’re in Chicago with kids, museums might not be top of their wish list. But this one definitely deserves a spot.

Immediately next to the skating rink at Millennium Park you’ll find the Art Institute, one of the most impressive galleries I’ve ever visited. We particularly loved the modern American gallery, with a great collection of artists Flea has studied at school. Seeing works by Georgia O’Keefe, Edward Hopper and Kandinsky up close was really exciting for her, and she also loved spotting famous paintings by the likes of Picasso, Van Gogh, Lichtenstein and more.

As an aside, if you’re a Ferris Bueller fan, you’ll love channelling your inner Cameron, and staring at the paintings. It was a big bonus for this family!

If you’re visiting, it’s definitely worth noting that there are two entrances to the museum, each with its own cloakrooms – if you enter by the bridge rather than walking down to East Jackson, the queues are WAY smaller and less hectic.

Museum of Science and Industry

This place wasn’t on our original to-do list, but was a recommendation from the concierge and it was a-ma-zing.


Each Christmas, the Museum of Science and Industry hosts an exhibition of Christmas trees from around the world. There are more than 50 big trees, all decorated by different ethnic and national groups within the Chicago area. There’s a Belgian tree (decorated with waffles, natch) and trees decorated by Korean, German, Canadian and countless other community groups.

It’s such a lot of fun – especially because twice an hour, the entire exhibition is dusted with ‘snow’ from above. It is a brilliant place to visit with kids

The museum is a great place to visit aside from the trees – there are huge exhibitions about farming (complete with tractors and combines), trains and transport (complete with replica trains and an entire hall filled with a mind-blowingly good model railway showing the journey from Seattle to Chicago), and on the week we visited a guest exhibition sponsored by Google all about robots and drones, which Flea loved.

My one warning about the museum is it can be a bit expensive. On paper, admission is $18 for adults and $11 for children, but this doesn’t cover access to all the exhibitions. We paid an extra $40 or so to access the robot exhibition and the space movie, but this didn’t give us access to the submarine or whale exhibitions – plan ahead and buy package tickets online for the exhibitions you want to see, it’s way more cost-effective.

The Sky Deck

view from sky deck

One of the must-do experiences for when you’re in Chicago with kids is the Sky Deck at the top of the Willis Tower.

This is one of the world’s tallest buildings – you shoot up in an elevator to the 110th floor of this skyscraper to a viewing deck with amazing views over the city and beyond. What makes the experience is the ‘ledge’ – actually a series of four clear glass boxes that jut out from the side of the building allowing you to stand on a clear glass platform with the city (and 100+ storeys of air) below you.

It’s pretty nerve-wracking even if you’re not scared of heights!

There are photographers at each ledge who will take your photo, and you can download/buy photos afterwards – but they’re just as happy to use your phone and take pictures for you. Do both is my advice – the official photographers actually lost our photos, so I was happy to have some on our phone as a back-up!

The best time of day to go is first thing, or at sunset – but check the weather as the views aren’t as good if it’s cloudy. My other tip is to pay for Fastpass tickets online in advance – these let you skip most of the lines and just take the lift up to the top floor – saving lots of time!

Sundaes at Margie’s

margies candies chicago

Everyone you meet in Chicago will tell you about their favourite place to get pizza and hot dogs so I won’t bother making a recommendation on that score – but you should definitely make the journey out of the city centre to visit Margie’s Candies – this diner has barely changed since it opened in 1921, serving fresh ice cream sundaes with hot fudge sauce. Make sure to visit the original site for the full experience!

Step inside this tiny diner with leather banquettes, cosy booths and table-top jukeboxes and you step back in time. This is the same place where The Beatles and The Rolling Stones came for Sundaes, and that’s quite a thrill. But the home-made ice cream is the real star – each sundae has three scoops of freshly made ice cream topped with home-made wafers and served with a silver jug of thick hot fudge sauce – it’s heavenly.

Zoolights at Lincoln Park Zoo

lincoln zoo lights

Head out of the city centre along Lakeshore and you’ll come to the Lincoln Park Zoo – a free city zoo within a park, which reminds me a lot of Central Park Zoo.

Your reason to come here, though, isn’t the zoo. At least, not in December. During the holiday season, each night, the zoo is lit up like a Christmas tree with the most dazzling, overblown collection of lights you have EVER seen. There’s Christmas music and you can walk around enjoying the Christmas spirit – and it’s all free.


If you fancy it, there’s ice skating, and you can pay $5 to decorate a gingerbread cookie, and there are stands selling popcorn, hot chocolate and beer. We loved watching some of the demonstrations, too – Flea’s favourite were the guys with chainsaws making ice sculptures, right next to the sea lion enclosure.

My top tip if you want to visit is to head to the park a little before sunset – the traffic gets crazy once the sun goes down (which is about 4pm in December) and lots of people get stuck in jams on the lakeshore roads.

Winterfest at Navy Pier

Navy Pier is one of the city’s biggest attractions. There are plenty of stores and a huge food court and it’s great to walk along the shore of the Lake and see ships in the distance. But during the winter, the real attraction here is Winterfest – an indoor funfair with snow-themed rides, cookie decorating (this might have got a bit competitive), and an ice skating rink.


You can buy an activity ticket that gives you unlimited access for the day, and there are lockers to store your bags and valuables. We spent a morning here when the rains hit, and it was perfect – although the ferris wheel wasn’t working on the day we visited, which was a shame. Tickets cost $23, which I thought was really reasonable.

The Bean

chicago the bean

Just next to Millennium Park is another Chicago landmark – and a really fun place to take pictures. The Bean is the nickname of a sculpture that’s actually called “Cloud Gate” – it’s a huge, smooth silver sculpture that reflects the city and sky with amazing curves and angles. You can wander round it, under it, and it’s definitely worth stopping by to take some pics!

Is Chicago with kids a good destination at Christmas?

Is it cold in Chicago at Christmas? Yes, it’s pretty cold. But if you wear gloves and a hat and thick-soled shoes, you’ll be fine. Take a face mask or scarf you can pull up, too – the wind can get pretty frosty on cross-streets, and you’ll feel it on your nose. When we visited (the week before Christmas) the temperature was between minus 4 and plus 2 degrees.

It’s also noisy – if you’re high up in a hotel, the winds coming off Lake Michigan will creak and groan like an old lady – this isn’t called the windy city for no reason! We were so lucky Four Seasons plans ahead and puts ear plugs in its lake-side rooms. But definitely think ahead and if you’re a light sleeper, book accommodation close to ground.

The wind and cold are just part and parcel of a Christmas trip to Chicago with kids, though. There are so many family-friendly holiday sights and activities to explore that you’ll never be bored here. It might just be my favourite US city so far!

6 thoughts on “Top Tips for Winter Trips to Chicago with Kids”

  1. Great Post Sally! Yes Millennium Park is probably the best park we have been. My kids loves it! Although, it’s a medium sized park I really like how they divided the sections. It’s a bit overcrowded but it’s very clean and has good music. Also I’d recommend the Adler Planetarium, the interactive and exhibits are awesome also the food in the cafeteria is good. Really great experience!

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