I used to live in Chicago and miss it so much. Of course I love Australia but man oh man, I miss the cold winter to get into the Christmas spirit
Map
Sections
5
Friday 🌃
Saturday 🎄
Sunday 🥞
If You Have More Time 🍷
Where to Stay 🏨
Friday 🌃
Take the Metra, El or Drive in. Check in to wherever your staying and enjoy the rest of your evening
An absolutely iconic view, ESPECIALLY in the holidays (when you can see the Millenium Park Tree)
Cindy's Rooftop
Another option is the Maggie Daley ribbon but I think ice skating under the bean is just too iconic
Millennium Park Ice Rink
Take the CTA red line up to the Addison Stop and go to any of the MANY holiday pop up bars for a drink. They go all out and you cant miss!
Wrigleyville Christmas Pop-Up Bars
Saturday 🎄
Get ready, its going to be a jampacked day!
Start your day with a gingerbread donut and a coffee from Stans, you're going to want something hot for your big day of exploring!
Stan's Donuts & Coffee
Continuously voted one of the best Christmas Markets in the US, this is a must do for any Chicago Holiday trip. Get there early, it gets crowded!
Christkindlmarket Chicago
Chicago is known for its food halls, sort of like fancy cafeterias (but better I swear!), if you haven't eaten too much at the market- go here!
Aster Hall
Ok nows your time to explore, shop and see the Holiday Windows- ill add some of my favorite stops!
Magnificent Mile
An iconic photo stop
Another favorite, the Wrigley building Christmas tree. Merry Christmas!
Be prepared for crowds!
Macy's State Street Holiday Windows - Chicago Loop Alliance
Okay now its time for the evening- I go EVERY YEAR Im in town- be aware you need to prebook!
ZooLights Presented by ComEd and Invesco QQQ - Lincoln Park Zoo
After zoolights, warm up with a mulled wine at this covered rooftop bar that overlooks the zoo
The J. Parker
Sunday 🥞
Time to go home :( But first, a few more things before you leave
Kasama was made famous by The Bear. and I can vouch for its deliciousness!
Kasama
You cant leave Chicago without brunch, heres a few- but Ill make a separate tip for my favorite of the bunch!
Chicago’s Best New Brunches
A Chicago classic- Enjoy lunch or a tea at the Walnut Room. Make sure to book WELL in advance. Like literally at least a month in advance.
The Walnut Room at Macy's
One of my favorite boutiques in Southport Corridor for great souveniers!
Alice and Wonder - Chicago Fashion Boutique
If You Have More Time 🍷
Staying for 4 days? 5? Heres more stuff to do for more time to do it
Time to rug up, if you can handle the freeze get out on the lake and take a holiday cruise
Chicago: Christmas Eve Lake Michigan Gourmet Dinner Cruise
If you'd rather not think too hard and figure out the CTA, take a tour that will show you all the best holiday lights
Chicago’s Festive Lights: A Magical Christmas Journey
If you can swing another full day, try a high tea, the Langham does a great one
Palm Court - The Drake Hotel
Every Holiday Season the Museum of Science and Industry puts up more than 50 trees, each decorated in honor of traditions from countries around the world. Its gorgeous
Christmas Around the World- MSI
This one takes a bit of advanced planning but if you can see where the holiday train is heading at what time, its a sight to behold
CTA Holiday Train & Bus - CTA
A gorgeous holiday tradition and for good reason
The Nutcracker - Joffrey Ballet
Every year Second City puts on a holiday themed show- and in a city famed for its comedy scene, its not one to miss
Holidays at The Second City
Where to Stay 🏨
Note: I usually stay with friends and family, and obviously before I had my own apartment but in the few times we do stay in a hotel, I have some opinions
Its super comfortable, super affordable, right in the loop AND kitty corner from the Christkindelmarket
Staypineapple, An Iconic Hotel, The Loop
Another fabulous hotel option. It overlooks the river AND has an amazing holiday pop up Rooftop bar I highly recommend
LondonHouse Chicago, Curio Collection by Hilton
Another classic, they also do an amazing high tea
The Langham Chicago
This hotel overlooks Millenium Park BUT over the holidays they create an Apres Ski Chalet themed room
