I spent a few months in Chicago during the holiday season of 2022 working a travel nurse contract. I did quite a lot in my time there, and Chicago is a great place to visit during the holiday times! It being a large city, there is always something going on. Read on to find out what you might find on your next visit.
Where to Stay
First things first. When you’re visiting Chicago, you want to be in a good location to early walk around or grab the L train. Here are some good options in downtown that will be the ideal spot for all the fun!
Halloween and Fall
Go see a show
Specifically, Wicked! I had a friend come to visit rights after Halloween and we went to see Wicked at the Netherlander Theater. It was such a great show! I would recommend it to anyone in the area during the time its on. It puts you right in your feels, but also has a sort-of festive vibe during Halloween. And afterwards you can go find somewhere to have a drink!
Halloween Pop-up Bars and Haunted Houses
Nightmare on Clark Street is actually unique in that it is a restaurant/bar AND a haunted house. There are 3 stories in this place full of ghouls and goblins ready to jump out and scare the life out of you. Afterwards, you’re welcome to enjoy some yummy food, festive drinks, and lively music. If you survive, of course!
Nightmare on Wacker Drive is located inside the LondonHouse and is a fancier alternative to the craziness on Clark. Tickets are required. There is a costume contest after midnight, and they have DJs playing all night long. You can of course find loads of drink options and some snack-y foods to eat as you party the night away.
Jack’s Pumpkin Pop-Up is one of the most well-known Halloween/Fall themed pop ups in the city. They’ve got a corn maze, lots of fun fall treats and drinks, games, and you can even buy your pumpkins here! The only down-side in my opinion to this Holiday fun, is that it is sort of on the outskirts of the city. This makes it less accessible if you are in the city and want to stay in the city.
Go to a Bull’s Game
With basketball season just getting started, what better way to get a feel of Chicago than to go to a Chicago Bull’s game? I went with a friend, and we had a great time! The bulls lost int he last few minutes unfortunately, but it was fun anyways. The United Center has a great set up for Ubers/Lyfts, which is nice if you’re planning to have a few beers.
Christmas
The Christmas-time festivities have to be the most intense part of the holiday season. Of course, as it gets closer to winter, the temperatures start to drop and you’ll often see some snow in December. Lights go up everywhere; on every building, every neighborhood has their specific decorations for the streets and landscaping, and you’ll hear Christmas music everywhere you go. This all begins immediately after Thanksgiving, and even some things are going on before Thanksgiving has even passed. There are a few iconic Christmas things you should do if you are in Chicago this time of year.
Christkindl Market
There are actually 2 locations for the Christkindl market now; one in downtown near Macy’s and Millennium Park area, and one in another spot that changes year to year. You’ll have to check the website closer to the holidays to actually know where it will be. This market is based on German and European traditions. You can buy gifts at the market, different foods, and most of all, mulled wine. There is typically a long line to get inside, and it is always crowded, so be prepared for that.
Go see a show
I had a friend come visit one weekend while I was in Chicago and we had plans to see the Nutcracker and go to alllllll the Christmas bars. We were not disappointed! The show, performed at the Joffrey Ballet was amazing! Although it may sound cliché, I would definitely recommend going to a show while you’re in Chicago. No matter what time of year, but especially during the holidays.
Christmas Pop-Up Bars
From the show, we went to Clark Street where we found the whole street had converted it’s usual bars/restaurants into Christmas themed masterpieces! My favorite was Elf’d Up– obviously an Elf themed bar. The drinks there were so fun and delicious! Plus, they decorated over the top just like Buddy would.
Frosty’s was probably my second favorite, but it was a ways off of Clark Street. We had to get tickets for this event beforehand, but it was really fun! You can also choose tickets that include “free” drinks or not. Randomly, it is just in a warehouse kind of in the middle of nowhere, so just be aware of your surroundings here. The interior was insanely decorated and there were multiple floors/areas where you could dance, drink, and chat.
Millenium Park
This might be a more tourist-y spot for things to do around Christmas, but it is a good one nonetheless. There is an ice skating rink installed at the front of the park, plus they put tons of lights up to give it that winter wonderland ambiance. There are places to rent your skates, along with a few places to get hot cocoa, drinks, etc. You have to book a time to skate online. The rink is typically open from mid November to early March depending on weather conditions.
If you want a little less crowded skating rink (and one that isn’t your typical oval shape), walk up E Randolph Street a bit to Maggie Daley Park. They have an ice skating “ribbon” during the holidays. You can bring your own skates here, too if you like! You can see the ribbon in the picture above.
There are a million other things to do in Chicago during the holidays, but this will give you a good start! Is there anything you’ve done that you recommend? What’s your favorite place to visit during the holidays? If you want more big city content, here is a post about rooftop bars in NYC!
