For the third year in a row, we escaped this past weekend for a heavy dose of holiday memories to a city that pours out festive feels from every corner, every storefront window, every street musician.
My kids look forward to our Christmas weekend in Chicago as much as Christmas itself, but this year perhaps no one was excited about this trip as much as Lainey. Her best friend Maggie moved to a Chicago suburb over the summer, and while the loss of her presence here has been patched over with FaceTime calls and daily texts, technology has nothing on the hug they shared an hour after we arrived and the three days that followed that included these two joined at the hip.
Christmas in Chicago musts for us include:
State Street Macy’s window displays.
Numerous stops for hot chocolate while we sightsee.
Riding the train.
Pictures on my friend’s apartment stoop.
…and so many night walks where we point out Christmas trees in windows and look for parties and pick which front door decorations are our favorites. We imagine the stories that are written in all the buildings we walk past, and my dad provides an ongoing soundtrack with the portable speaker he keeps in his pocket, full volume–all the Christmas carols, all the time.
New favorites this year:
Tea at the Drake Hotel with our friends and Brett’s sister (who is moving to Naples in just days, and we are so excited!).
A night time carriage ride through the city (we used Antique Coach & Carriage Co., just outside the old Water Tower). We all loved this one so much and will definitely do it again.
You bundle up beneath blankets and ride through the most festive streets, even a little stretch along Lake Shore Drive. We sang Christmas carols while the kids hollered to onlookers various holiday greetings that, I’m sorry to say, included “Tooty Christmas!”, “Happy Toots!” and “We Wish You a Merry Fart!” (followed by hysterical laughter).
Macy’s Santa. We’ve never attempted Santa in Chicago before because the lines were too long (because it’s the REAL Santa) and Nella isn’t much for seeing him face-to-face, but I was on a one-on-one date with Nella and ventured down to the enchanting Santa Land in Macy’s where Santa was visiting. I thought maybe we’d just check it out, but we came during a time when there were no lines, so I pushed it a little further, standing in line and suggesting we’d just “look at Santa.” not sit with him. When it was our turn, the red velvet curtain pulled back to reveal this magical festive nook and the kindest Santa, straight from the North Pole. When Nella was hesitant, sweet Santa suggested I sit with her alone while he walked away. Once she was comfortable, we asked if he could come back and she said yes. I asked if I could step away to take a picture, and she nodded yes again. And then Santa reached for a book and asked if he could read it to her. I didn’t think to check my camera settings–just started snapping. Magic, I tell you.
I don’t know how I missed the little playground tucked right next to the fire station near Michigan Ave all these years, but I’m so glad we found it this year. It was warm enough that the kids could actually enjoy a good half hour playing there before our next cocoa stop.
Another favorite this year was Christkindlmarket, an open-air German holiday village full of gift vendors and German food. I enjoyed my first (and hopefully not last) cup of Glühwein, the most delicious hot spiced wine, and picked up some keepsake treasures.
At the Bean, it was surprisingly warm enough for the kids to take off their coats for a bit.
Even though we didn’t end up with snow, we feel so lucky to have enjoyed such beautiful weather when we’ve experienced brutal winds on this weekend before. The sun allowed for more outdoor exploring.
And when the sun went to bed and the cold came creeping in, we made my favorite memories–the indoor kind, not dependent on what the city gave to us but what we brought to it.
…our dance moves…
…and the suitcase of things we packed to “make it special.” Snowmen marshmallows for cocoa, a Christmas puzzle, our favorite jammies, card games and a candle that smells like a Christmas tree farm.
My dear friend lets us stay at her family’s apartment, and so many of our most memorable moments on this weekend happen inside this special place, set up with toys and so many little personal touches.
I think we could have skipped the city adventures altogether and let Nella play in this secret nook the whole weekend, and she would have been perfectly happy.
We’re smitten with this city and so grateful to tuck away another weekend of December memories together here.
…and even happier to come home to be together as a family, where we belong.
xo to you and yours.