The holiday season in Chicago is simply magical if you ask me. The city loves to celebrate and that it does in a very festive fashion! Since I was a little girl going to Downtown Chicago during the holidays has been something that has brought joy to my world and as an adult that is still the case! I thought I would share with you some of our long-standing traditions of places to visit for #FestiveHolidayFun in #SweetHomeChicago and I thought I would also share with you some new things that have popped up that are also worth checking out!
Museum of Science and Industry

Since 1942 this beautiful holiday tradition has been part of the Museum. It’s a tradition that my Mom used to do with her Grandmother and Mom and it’s one that my Mom and I have done since I was a small girl.
Trees from around the world are decorated by local Chicago groups from that country and each year they bring in new decorations, so while the countries the trees come from may be fairly consistent (though new ones are added too!) the décor changes and it is so much fun to see what they have chosen to represent their country on their tree each year.
As you walk into the main hall of the Museum you will see the great tree and its décor changes annually as well. The trees from the various countries fan out on this level from this area. Each tree has a plaque that tells about the country’s holiday traditions and who decorated it. It’s a wonderful way to learn about how others celebrate!


This is a holiday tradition that I do my best to never miss! It doesn’t hurt that it’s in my favorite museum on the planet of course! But no matter how you celebrate the holidays, this display of trees is one that everyone can enjoy.


And as you wander the Museum you may see some other holiday fun such as the Christmas décor in the baby chicks exhibit! We visited for Members Evening so the chicks were not out but I just love that even the baby chicks celebrate!
Christmas around the world is included in your general admission for the Museum and typically runs from mid-November to the first week of January. Be sure to click below and check the website for details!

Winter Wonderland at Gallagher Way/Wrigley Field & Wrigleyville Festive Fun
This was new in 2022 and since we are HUGE Cubs fans we decided to check it out. (I mean anything that allows you to go onto Wrigley Field has got to be pretty cool just for that! We had fun in 2022 and were thrilled when we saw it was back for 2023 so naturally we planned to go!

In the Gallagher Way area there’s the Christkindlmarket Wrigleyville which has wonderful shops, food and beverages. No ticket is required to access this. It’s a perfect place to do a bit of holiday shopping and to grab a warm beverage to wander with!
To access Wrigley Field there is a small fee but it’s well worth it. They have done a fantastic job of decorating in baseball and Cubs holiday décor throughout the entire area including the walkway areas.

On Wrigley Field there are some great light displays (naturally my favorite is the baseball but I also love the penguin in Cubs colors!) as well as various rides and games. (These rides and games are for an extra fee.) We are much for the rides and games but we love just being there to take in all the holiday festivities.

They have a big lodge where you can get food and beverages and even the stuff to make smores! Yum! Private chalets and igloos are available for group rentals and I really want to try and get a group together for that next year!
This festive fun would be fun for anyone but especially if you are a Cubs or baseball fan… all I have to say is Wrigley Field!!!

I certainly hope this is back and even better (if the trend continues) in 2024! Gallagher Way Winterland
I was also excited to say that many bars around the are embracing the holiday festivities and have a variety of pop-up bars. We visited Mistletoe at Hush Money which is across the street from Wrigley Field at the Hotel Zachary. Great cocktail menu and some delicious food too. (Next year I think I am going to need to get a group together to do a long weekend of Wrigleyville Holiday Festive Fun!)


You can judge me if you want to but yes, I am already planning ahead to next Holiday Season!! Who’s with me?
The Walnut Room at Marshall Fields
Yes, You read that right… Marshall Fields… ok the signage may now say Macy’s and your bill will now say Macy’s but for those of us who grew up there, it will ALWAYS be Marshall Fields.

While the name may have changed officially, one thing hasn’t, the tradition of The Great Tree in The Walnut Room. Started back in 1907, this 45 foot tree has become the centerpiece of the Walnut Room and a tradition for generations to visit! (A few years ago we met a woman who had been visiting at Christmas for 90 years! Amazing!)
The Walnut Room restaurant is one of the most highly coveted reservations in the city when the Great Tree has been put up. Each year the tree’s décor changes and it’s always a fun surprise to see what they’ve done. This year’s tree is truly one of my favorites!


They do accept (and encourage) reservations but word of warning – they fill fast! Apparently this year they were full for the whole season in early November and I am not sure when the reservations opened up. They are open for lunch and dinner during the holiday season and on certain days they even have breakfast. We didn’t have a reservation because I was not certain when I was going to be able to visit so we took our chances at a walk-in reservation by arriving half an hour before the restaurant opened on a weekday. (I wouldn’t dare try that on a weekend!)


We got seats at the Wine Bar which allowed us a great view of the tree even though we weren’t right next to it. Honestly, we just want to be in the room where it happens (sorry – couldn’t resist a Hamilton reference!) so we are ok anywhere in The Walnut Room to bask in the splendor of the tree! Plus once you’re in there you can get closer to the tree to take pictures etc.
I failed at getting pictures of the food (I will do better next year I promise!) but one of our musts is to get a drink that has the commemorative mug that goes with it! And I will tell you that you can’t go wrong with the Chicken Pot Pie which has been on the menu there pretty much forever – it’s a classic and it’s delicious!
We had a sweet time at The Walnut Room and can’t wait to visit again next year! (Guess I better check monthly to see when reservations open up!)
Oh and on your way in or out of the building don’t forget to check out the window décor! This changes annually too!

Pinkmas at The Museum of Ice Cream
This was a new one for us this year, not just Pinkmas but The Museum of Ice Cream as well. I’d noticed it when staying at the Intercontinental Hotel on Michigan Avenue because it was right next door. When I looked at the website in the fall they were already advertising that Pinkmas (they holiday festivities) were coming so I thought we’d check that out as part of our Festive Holiday Fun. I am so glad we did!



This adorable and incredibly Instagramable immersive experience will bring out the childlike joy in anyone! Ice cream and all that goes with it is everywhere! You start off “riding a train” that is ice cream themed and even done to the theme of the Chicago L! (I adore that the incorporated local things throughout the experience.
There were Christmas trees, presents, and ribbons everywhere along with their usual ice cream elements. And oh yeah, ice cream… folks… it’s unlimited!


The décor throughout was super fun and there were many interactive activities. I don’t want to give away all the fun so you just have to go check it out… especially the Chicago nod with the hot dog!!


And it all finishes in one of the most amazing things I have ever seen…. A sprinkle pool! Okay so they aren’t real sprinkles but I don’t care. It’s amazing! And you can leap into it. So fun!!


No matter if it is Christmas or any other time of year I think it’s definitely worth a visit to The Ice Cream Museum!
As you can tell we had a lot of festive holiday fun again in 2023. Perhaps this blog gives you all a MAJOR head start on your 2024 planning!
