Christmas in Chicago

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Plan a Chicago Staycation full of holiday cheer with these fun and joyful Chicago Christmas ideas! From bright light displays and Christmas trees everywhere to Christmas movie double features and the Polar Express, there is something for everyone! Plus, I have the perfect hotel recommendation for all your staycation needs: The St. Clair Hotel! 

Chicago Christmas tree at Millennium Falcon downtown chicago


Winters in Chicago are cold, slushy and (of course) windy! January through the beginning of March is basically my least favorite time of year, and my birthday falls in that window. 

I am definitely a Chicago summer kind of gal! 

However, Novembers and Decembers in Chicago are some of my favorite as the city celebrates the holiday season! 

When we lived in Chicago proper, my husband and I took full advantage of Christmas in Chicago, going out multiple times a week to take in the Christmas markets, the shows, the decorations and overall joy of the season. 

Even now that we are living out in the suburbs, we still find time to take in Chicago Christmases because they really are magical! Whether we sneak in a date night the two of us or I head into the city with my sister, taking in holiday time in the city is a must. 

The St Clair Hotel in Chicago off of the magnificent mile

And we look forward to when our kids are a little bit older so we can book a room at The St. Clair Hotel – Magnificent Mile for a Chicago Christmas Staycation a family holiday tradition! 

The St. Clair is situated in the heart of downtown Chicago in River North just one block off from the Mag Mile. It’s in easy walking distance to 360 Chicago Observatory, Navy Pier, the River Walk, the theatre district, and Millennium Park. 

When I stay here, I love that I get to walk down Mag Mile with a coffee and take a look at the art displays or pop into stores. 

Art display of the old chicago water tower sculptures decorated and displayed on the magnificent mile

It really is in the perfect area to enjoy everything Chicago has to offer all year long, but especially for a holiday staycation. 

The St. Clair provides all the amenities we expect from a city hotel at a more affordable price. In fact, the rooms are much bigger than many other hotels I’ve stayed at in the city before. I’m also pretty in love with the large full size shower, which is pretty rare in the city. 

Plus, for family trips, you can even upgrade to a double king room so there is plenty of space for everyone to sleep. 

It’s the perfect budget hotel in a great location! 

king bedroom photo from st clair hotel in chicago river north Hotel room at the St Clair Hotel on Chicago's Michigan Avenue north of the river

So check out tons of Chicago Christmas Events and Shows below so you can plan your perfect holiday staycation at St. Clair in my favorite city! 



No visit to Chicago during the holiday season is complete without a stop at Christkindlmarket. It’s a great place to look for unique gifts, especially ornaments and nutcrackers. 

Plus, you will definitely want to indulge in the food like the potato pancakes and pretzels, of course! My favorite snacks to purchase though while I walk around the market is warm candied nuts and a mug of Glühwein which is a traditional hot spiced wine. 

If the weather is nice, it gets very crowded in the evenings, so I prefer roaming around during the afternoon of a weekday if I can. 


With two locations to choose from for a fantastic holiday zoo lights display, you can’t lose! It’s an amazing family outing that the adults and kids will love. 

Lincoln Park Zoo will be the easiest location for anyone staying in the city. Plus, access to the zoo is free which is always a bonus! In addition to 2.5 million Christmas lights, you will find ice sculptors, carolers, and Santa Claus. 

If you are local, Brookfield Zoo is also a great choice! The zoo is larger and includes a skating rink in addition to magician, dancers, special shows, and more! 


Similar to a Zoo Lights experience, the Morton Arboretum lights up a one-mile path with a magical display of lights and seasonal music for their Illumination. After the cold walk, you can warm up by a fire with hot cocoa and s’mores! 


Honestly, I am not an ice skater. My family growing up was not into outdoor winter activities and the only time I have ice skated was a horrible school field trip experience. I mean – who thinks taking a bunch of 8 year olds to an ice skating rink is a good idea?

However, ice skating at Millennium Park is magical and a spot I always take friends and family. Maybe when the boys learn to ice skate, I will finally learn, too! 


Every Friday from the end of November to the Friday before Christmas, you will find carolers at the Bean. It’s free to attend and led by an amazing musical groups, including Chicago Children’s Choir and the Voices. 

After caroling, you could just pop over to the Millennium Park Ice Skating Rink! 


My brother and his family do the lights festival almost every year, and the St. Clair hotel is in the perfect local off the Mag Mile for seeing this event. 

The Lights Festival is a two day event (beginning November 22, 2019) that includes family friendly events, Santa Claus, special experiences and offers at stores, tree lighting, a parade with Mickey Mouse and Minnie Mouse. and fireworks!

It really is the perfect launch to the holiday season for the whole family! 


The 45-foot-tall tree sits inside the middle of the Walnut Room with over 3,000 ornaments and 6000 lights! It’s a beautiful indoor tree to marvel out during a good meal! 

If you don’t want to splurge on the food though, the tree can be seen from outside the restaurant. It’s works as a perfect holiday reprieve from the cold.

But the 45-foot-tall tree, which sparkles with 3,000 ornaments and 6,000 LED lights, can be viewed from outside the restaurant, which means that you won’t have to splurge for a chicken pot pie simply to experience one of the most spectacular holiday displays in the city.


More than 500 Christmas trees decorate this indoor amusement park at Navy Pier. There are winter themed rides, craft stations, ice skating, mini golf, and aerialists on the weekends. 

Plus, Navy Pier has also added a winter market to add to the holiday fun! 


We are always up for a trip to MSI, but we really love their Christmas Around the World exhibit! The main gallery is decorated with over 50 trees designed to represent different countries with information about their traditions. The weekends also include live performances! 


This is an official Polar Express experience with a live recreation of the movie! They encourage you to wear your pjs, hot chocolate and cookies are served, kids are gifted a silver bell, and Santa makes an appearance, of course! 

Every year moms talk about this experience online as a must do holiday activity and I’m really excited to do it with the boys. The only reason we’re not starting this year is because we have a big trip planned instead for the holiday but I will definitely be buying tickets next year! 



If you have never seen a professional performance of The Nutcracker, you are missing out! We are so lucky to have the Joffrey Ballet in Chicago and their Nutcracker is amazing. 

We took my nieces a few years ago as part of their Christmas gift and will definitely be taking the boys in the future. 


The Christmas Carol at the Goodman Theatre is a Chicago tradition! The annual performance is a must see at least once for holiday celebrations. 


If you love classic movies like I do, attending the Music Box’s Christmas double feature should be a must on your holiday to-do list! It’s a long standing Chicago Christmas tradition. 

White Christmas is the perfect choice as a fun sing-a-long and It’s a Wonderful Life is a must, too. The event also includes Christmas carols led by none other than Santa Claus! 

St Clair Hotel logo


There is still time to book your fun Christmas staycation at the St. Clair so you can enjoy your favorite holiday traditions! 

The St. Clair is part of The Red Collection, a local soft brand of Red Roof that is focused on bringing unique localized experiences while staying true to the Red Roof philosophy of value, comfort and affordability. Which means modern hotel with boutique city amenities on a budget! 

The Red Collection Hotel in Chicago


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