The PERFECT itinerary: Christmas in Chicago
I don’t know why I never thought of Christmas in Chicago before but now I can’t imagine Chicago without Christmas!
And if you think about it, there are SO many Christmas movies based in Chicago, including the greatest movie of all time: Home Alone. Seriously, this is one of my favorite trips of all time and I’m so excited to share it with you so you can make the best Christmas trip in Chicago ever!
Since this was the first time in 10 years that I’ve been to Chicago, I mixed the classic tourist attractions with Christmas fun to give you the Perfect Itinerary for Christmas in Chicago!
What to Do
Christkindlmarket
Free (entrance)
The Christkindlmarket is held at Daley Plaza in Downtown Chicago and is a hit among tourists and locals. And when I say hit.. I mean it. We tried 3 days in a row to get into it and each time the line got longer & longer until it wrapped around the street multiple times. It was worth any wait though. Inside, you’ll find tons of pop-up stores featuring gifts and food from all over the world. I bought some handmade ornaments from Ukraine, German donuts and strudel and Belgian hot chocolate in the anniversary mug.
If you want to beat the line, try to go during the weekday or 30 minutes before opening. Or if you still prefer online shopping to in person, you can enjoy some of the fun by checking out the Christkindlmarket website, which features some of the vendors!
Note: If you want more of the fun, there’s a second location in Wrigleyville!
Chicago Gangsters and Ghosts Tour Chicago
$$
This goes towards the top because it was SUCH a fun experience! We all know what Chicago is known for – most of the world has heard of the name Al Capone. The Gangsters and Ghosts tour is a 2-hours long walking tour that gives the ins and outs of Capone, while hitting on lesser-known killers like H.H. Holmes and the rest of the tragedies that (literally) char Chicago’s past. We even got to stop in the Palmer House Hotel, where Capone held many events. We got blessed with wonderful weather for winter in Chicago and an amazing tour guide, which helped make the walking tour even better!
360 Chicago
$$
If you are looking for Insta worthy photos or to sit and ponder I wanted to hit this spot during sunset so we took the subway up around 3 pm. I would recommend getting tickets online or showing up at least this early to hit sunset at 4:15 pm.
Pro-tip, if you want to get the best views and pictures, plan to be inside the observation tower ~20 minutes before sunset. Plan for about a 15-minute line to go up the elevators, even with pre-bought tickets and another 15 minutes to stand in line for tickets.
Lincoln Park Zoo Lights
$
If you’ve never been to Zoo Lights before, now is the time to go! The zoo lights at Lincoln Park Zoo is not only unbelievably reasonably priced ($5/person!) but it’s fun for all ages – and you’ll find no shortage of people there. In fact, the event is so popular that I recommend you buy tickets online or risk the possibility of not getting in. I saw a few groups get turned away at the door. So what is it? Millions of lights cover the entirety of the zoo in an after-hours walk-through event. Some of the animals even stay out throughout the early evening to enjoy the magicalness with you. Craving some adult fun? Grab a cocktail or a s’more at their Christmas-themed bar.
Christmas animals and dessert, what more could you ask for?
Millennium Park
Free
Ice skating, caroling, Christmas trees and more! Millennium Park is a great place to spend an afternoon with the family or that special someone. The Park includes a giant Christmas tree adorned with loads of lights for the perfect photo opportunity. Swing next door for a skating rink that’s free to everyone, just bring your skates or rent some there! Both are located next to the iconic Bean, a sculpture that represents Chicago as much as the people themselves. And even the Bean joins in the festivities with caroling every Friday at 6 pm. If you’re willing to make the walk across the bridge, you’ll find another ice skating rink that features Disney’s Frozen “on ice”.
Light show at Merchandise Mart
Free
Every evening, there is a free light show from 7:30-8:00 outside of the Merchandise Mart facing the river. The show is a perfect stop while you’re waiting for a table at Lou Malnati’s. The massive video installation is synchronized to music and this year includes scenes from The Nutcracker.
For the best view, hit the Chicago Riverwalk between Wells and Franklin Street.
What to eat
Classic Deep Dish at Lou Malnati’s
I am not a deep-dish girl but I’ll admit, this place was pretty good! We tried the cheese bread which was so delicious – and could’ve easily served 6 people – that we ate the entire thing between the two of us. Part of it was that there is a 35-40 minute wait on any deep dish – we tried classic pepperoni & sausage deep dish pizza – but it’s definitely worth it. Malnati’s was the place to make Chicago Deep Dish as famous as it is today, so much so that there’s still a 1.5-hour wait to get into some of their locations. Luckily, there are multiple locations across the city and though they don’t take reservations (like many restaurants in Chicago) you can either check online or call to determine the wait time.
Magnolia Bakery
You might have heard of this place if you’ve visited NYC – and it’s as big of a hit in Chicago. I’m all about desserts so of course, we had to go. We split their chocolate cupcake and banana pudding, which they’re famous for. Not only was the inside of this place adorable – imagine a quaint countryside bakery – but the dessert lived up to the reputation. My favorite part was that they have Holiday themed desserts! I wish I could be there for their New Years’ Eve funfetti cupcake!
Urbanspace
We stumbled into this place last minute after striking out on wait times with what seemed like every other restaurant in Chicago. Also an NYC copycat, Urbanspace is like an adult cafeteria with so many options I debated trying a little bit of everything. From donut milkshakes to crab-filled mac-n-cheese, to plant-only food and an end bar, there’s an option for every member of your squad. The best part? The wait is 15 minutes tops.
Nutella Cafe
I didn’t actually get to go here, sadly, but who knew they had an entire cafe dedicated to Nutella treats? Someone please go and report back!
Where to stay
The Hotel
I searched for hours looking for the best quality to price and safest hotel and the Renaissance Chicago Downtown won. It’s located right next to the river in downtown and is within walking distance of Millennium Park, Magnificent Mile, and is in the heart of Chicago’s Theater District. It has the cutest rooftop bar where you can enjoy a cocktail or food around the firepit with your friends.
Tip: If the Renaissance is full, try the Westin Chicago River North across the River!
Parking
No matter where you stay, parking is going to be costly. The Renaissance offers valet parking for $76/day or there’s a street garage across the street. If you choose the latter, make sure to visit the IParkIt website before going to save up to $70 on your trip.
How to travel
Chicago’s transportation is amazing for such a big city. There are so many options! First, if you’re staying downtown, almost everything is within walking distance. But if something’s too far, there’s the train, the “L”, and the bus to get you there. I rode the bus from the Renaissance hotel all the way to the Lincoln Park Zoo with a few blocks walking in between. The greatest part is that you can buy a 24-hour ticket that includes all forms of transportation for $5! This ticket can be bought at a station near the train or through the Ventra App, where you can also reload the tickets instead of stopping back at the ticket station.
What to Skip
Navy Pier
This was just not worth the time nor the money unless you’re going for the Ferris Wheel, Shakespeare Theatre, or their Holiday Light Up the Lake event. In the summertime it may be a different story, since it looks like there’s boats to take you out on a cruise (fun!). But in the Winter, there’s really only food and a few stores to pick from.
Warning: Do not set any personal items down here, even for a second! My Grandma was shopping in one of the stores and placed her phone on the display table literally in front of her while she was talking to the employee. The phone was gone immediately and no one claimed to be responsible.
State and Lake Chicago Tavern
I had so much hope for this new restaurant, located beneath The Wit hotel. The inside was a mix of rustic cabin and industrial, with quirky decor like a reflective deer or patterned plaid chair. It was warm and inviting and the best part, there was no wait! Everything about this place made me want to like it. Unfortunately, it was severely understaffed, which is why it ended up on this list. It took a long time to get seated, drinks or food. The food itself was decent, but I’d give this place a little bit more time to get its feet underneath itself before you hop in. Unless you’re starving (like we were) and want to cut your wait time in half!
Garrett Popcorn
I know I’m going to get a lot of heat for this one, but here’s the truth. The cheesy popcorn at Garrett’s? Overrated. Now I’m a major popcorn lover and even made my family wait outside in line in the cold for this but I have to admit, I wasn’t very impressed. We only got the Cheesecorn, which was mistake number one, but it was way too cheesy! I could only handle a few pieces at a time, which is not ever how I want my popcorn. The popcorn itself seemed pretty solid, but hopefully the other flavors are more balanced.
I hope this is the perfect itinerary for your Christmas in Chicago! If you have any questions feel free to drop a comment below!
Xoxo,
Gina
© Gina Spoden 2021
