Visiting Chicago during Christmastime is one of the best times to explore! The entire city is decorated beautifully and you’ll start to feel the holiday cheer just by walking around. It really does become the most wonderful time of the year (except for the below freezing weather). As long as you’re okay with a little chilly weather, you’ll enjoy all of the festivities during Christmastime in Chicago. Below is my list of some of the best things to do in Chicago during the holiday season! And don’t worry, there are indoor options, too!
Go Ice Skating in Millennium and Maggie Daley Parks
One of my favorite winter activities is going ice skating in Millennium and Maggie Daley Parks. Millennium Park holds the classic oval ice rink and Maggie Daley Park has a skating ribbon that has a winding landscape to provide a more thrilling experience. There is a rental fee to borrow ice skates, so I would recommend investing in a couple of ice skates and bringing them out to enjoy free ice skating all winter long. As long as you bring your own skates going ice skating is absolutely FREE! If you do decide to rent out some skates, the costs can range from $10 to $15 for an unlimited time. You can purchase your ice skate rentals on site, and there are also locker rentals available for purchase. If you’re interested in taking ice skating lessons, Millennium Park also offers free classes on select days. This would be a fun group activity for family and friends.
Visit the Christkindlmarket!
You can step into a Christmas wonderland by visiting the Christkindlmarket. This fun Chicago tradition originated in Germany and was brought to Chicago in 1996. There are two locations in Chicago this year: the Daley Plaza and Wrigleyville. Admission to the markets is free. The markets are composed of many rows of booths that resemble little cabins and are decorated beautifully with twinkling lights. Each booth is hosted by a local vendor where they sell their various treats. You can find many booths selling gingerbread, candy, mulled wine, hot chocolate, Christmas ornaments, and so much more!
My favorite thing about visiting the market is grabbing a mug of hot chocolate in their limited edition mugs that are specially made for the Christkindlmarket. They are super cute and fun to collect. I now have four of them! This year, they have the classic boot mug and the cutest penguin mug! I would recommend going just to grab one of the mugs. It costs $8 for a cup of hot chocolate or apple cider and includes the mug.
Quick note: Be prepared for a very big crowd. Every time I have visited the market, it has been very busy. This is important to keep in mind when planning a trip here, especially if you aren’t a fan of big crowds. I recommend visiting on a weekday as soon as it opens to avoid the highest traffic.
Attend the Christmas Tree Lighting Ceremony
The Christmas Tree Lighting is one of Chicago’s most beloved and longest-running traditions. This year was the 106th tree lighting ceremony and there is no sign that the ceremonies will be stopping anytime soon. Located outside Millennium Park on Michigan Avenue is the stunning 55-foot tall Christmas tree that is decorated with multicolored lights and a shining bright star on top. The tree lighting ceremony is accompanied with festive live performances and is followed with the Magnificent Miles Lights Festival parade. Admission for the tree lighting ceremony and the parade is free.
The lighting ceremony was on November 22nd, so it has already passed for this year, but it is not too late to stop by Millennium Park to see this giant, beautiful tree for yourself. It’s a great place to take cute Christmas pics! And also keep the tree lighting ceremony in mind for your bucket list next year!
Attend the Magnificent Mile Lights Festival
One of the best holiday festivities in Chicago is the Magnificent Mile Lights Festival. This event stretches across two days and features a variety of different activities. At the Lights Festival Lane, you can get your face painted; visit Santa Claus; sample some delicious treats from Garrett’s Popcorn, Frango’s, and more; enjoy live musical performances; and you can enter plenty of sweepstakes and giveaways at many of the festival booths. On the second night of the festival (following the Chicago Tree Lighting Ceremony), you can find a good spot to watch the magical holiday parade, which features Mickey and Minnie Mouse as they lead the parade while lighting millions of lights along the way. There is also a fireworks show to end the second (and final) night of the festival right above DuSable Bridge. And the best part is that the entire festival is FREE to attend!
Aren’t able to make it into the city for the festival? You can also watch it live on TV! Check your local listings for it. While this event has already passed, I recommend saving this for your future Chicago holidays! To read more about the festival, you can check out their website here.
Sip on Hot Cocoa from BomboBar
BomboBar has some of the most delicious hot chocolate during the winter months in Chicago. It’s only served during these cooler months, so I recommend stopping by to try some of the rich chocolate for yourself. It’s good at warming your hands (and your heart)! They have two different variations of hot cocoa: their Hot Chocolate and their Hotter Chocolate. The Hot Chocolate is your standard cocoa with whipped cream and chocolate shavings on top, while the Hotter Chocolate comes in two different flavors: S’mores and Funfetti. Both of these Hotter Chocolates are covered with loads of different toppings and look oh so tasty!
So which team are you? Hot Chocolate or Hotter Chocolate? I will say that they are both equally delicious, but if you are looking for a sugar overload, grab one of the Hotter Chocolates for the sweetest hot chocolate you’ve ever had!
Enjoy the ZooLights at Lincoln Park Zoo
The Lincoln Park ZooLights is a free light installation that is open to all ages. Some of the many activities you can do at the ZooLights include taking photos with Santa, munching on holiday snacks, drinking warm spiced wine or frosty beers, going gift shopping, seeing live ice sculpture carving, watching the Christmas carolers, walking through the light displays, and enjoying the musical light show. You can also purchase a ticket for a ride on the lit-up carousel, Ferris wheel, or the Lionel Train Adventure. There is also a light maze and cookie decorating classes (ticket required). So much to do!
While the ZooLights are usually a family-friendly activity, they do also offer one special event called BrewLights that is for adults only. And as the name suggests it is an evening filled with many beers and lots of cheer. The event is being held on December 12, and a ticket is required for admission to this event. To read more about the ZooLights (or BrewLights), check out their website.
Have a Drink at Frosty’s A Christmas Bar
Christmas-themed drinks? Yes, please! Frosty’s A Christmas Bar is a pop-up bar that comes around during the holiday season. This place is decorated to the max with Christmas decorations and is one of the most festive places you could visit. There are three floors of holiday cheer, two dance floors, four bars, and a non-stop holiday playlist. You can snack on holiday cookies and sip some merry punch while listening to Mariah Carey’s “All I Want for Christmas Is You.” Sounds like a dream. They also host singing Santa Claus shows! It doesn’t get more festive than that!
Tickets cost $15 to $30 and includes drinks with purchase. Admission is 21+ only. You can purchase tickets on their website. WARNING: Their website immediately plays loud holiday music. Do no open while at work (like I did, haha).
Walk the Magnificent Mile
The Magnificent Mile (aka the shopping central of Chicago) is completely covered with Christmas cheer during the holiday season. You can find holiday displays along the sidewalks featuring reindeer, sleighs, and little Christmas trees. It’s also the perfect place to visit to get some last-minute Christmas shopping done.
If you go to the Old Water Tower Place, you will also find the prettiest Christmas tree that I’ve been able to find in the city (at least outdoors). It has the cutest ornaments and looks so gorgeous in photos. I definitely recommend stopping by to see this tree while you’re here!
Visit the New Lightscape at Chicago Botanic Garden
This year is the first installation of a stunning light exhibit at the Chicago Botanic Garden. You can walk through a magical wonderland of lights. Even though technically the Chicago Botanic Garden is in Glencoe, it still makes it on this list because of how beautiful it is. The Lightscape is similar to ZooLights but what makes it stand apart is the largest light tunnel in the area, a choir of singing trees, a garden of fire, marshmallow toasting, and an interactive light exhibit with a spectacular finale. I haven’t been able to make it out here yet, but I’ll see if I get the chance later because this is definitely something on my holiday bucket list! You can purchase tickets for the Lightscape on their website here.
Visit Macy’s on State Street
Macy’s during Christmastime is one of the prettiest stores you could visit. The entire store on State Street is completely covered with Christmas decorations and screams holiday cheer. I was in awe when I walked in and saw how everything was decorated so beautifully. From giant snowflakes hanging from the ceiling to Christmas trees adorning each floor, you will definitely start feeling excited for Christmas after walking around the store. It’s also a great place to buy your loved ones some presents!
Visit Santa at Water Tower Place
The shopping mall in Water Tower Place is really fun to visit during the holidays. There are huge snowflake decorations hanging everywhere and lots of holiday shopping to do, but one of the best features is that you can visit Santa here! On the 7th floor, you can make reservations to take professional photos with Santa Claus. This is a very fun thing to do for the family, and you can also take your dog!
If you don’t feel like taking photos with a random man, you can choose to take family photos in a sleigh instead. However, for either option, you will have to purchase photo packages in order to take photos. There are many photo package options and some include a snowflake ornament with your purchase! For more information on visiting Santa, check out their website.
Visit the Christmas Tree at the Wrigley Building
The Wrigley Building has one of the biggest trees in the city. I love visiting this area because the entire section is decorated beautifully for the holidays and looks so adorable! I also think it’s a perfect spot for some Christmas pictures! While this tree isn’t as large or as decorated as the tree outside Millennium Park, it still has a charming look, especially with the cute teal bow on top. And the tree really pops against the white of the Wrigley Building.
Photo tip: Go early to avoid heavy foot traffic. Weekends are usually busy because people are out shopping so the earlier the better!
What do you think of all the holiday pictures? Do you think Chicago does Christmas right or is it not enough? Let me know your thoughts down below! And also add anything you think should be on this list!
Happy holidays to everyone and thank you for reading!