Chicago at Christmastime, 2021

Helloooo! Who wants to hear about Chicago during the holidays and how some things are amazing and other bits are… well, honestly a bit overrated. Overall, though? Definitely a worthy addition to our holiday tradition list.

So as I mentioned before: the boys are older, so time to shift up to new holiday adventures. I got a cheap rate at the same hotel we stayed at our last visit (score), so off we went one Saturday morning to our favorite playground, Chicago. Linus prepared by carefully packing all his favorite things, including beloved Sheepy, in a Natural Grocers bag.

Long time no see, evil robot Sears Tower.

Long time no see, rest of the buildings on the way to downtown…

Once we hit downtown, Scottie and I sweated the traffic and navigation turns while the kids ooo’ed and ahhh’ed at a downtown dressed up in holiday lights and decor.

And then: at the hotel! Took a bit to get in (it shares a valet station with two other hotels, so there was a bit of a line when we arrived), but once we did the staff was super nice and we got a great room way up high, with a view of our favorite restaurant as well as the firehouse below. And the alley to the secret bar was strung with lights!

The city view wasn’t too shabby, either. Linus was excited to have a good view of Marina City.

Several of the buildings had special holiday lighting.

We got nice and settled in and unpacked, and the kids of course were well engrossed in their devices, so it took some coaxing to get everyone back into their winter gear and out the door to check out downtown.

Lots of holiday-dressed bars and restaurants downtown this time of year! And the street-ery pop-up dining spots also looked rather festive.

The boys also had what appeared to be several sword-fights and battles along the walk.

Our first destination was the venerable Christkindlmarket. The downtown Chicago market has been around since the early 1990s, and every Chicago person I know hits it up every year. It always looks so lovely, that old European tradition of a holiday market brimming with booth after booth selling everything from treats and hot drinks to hand-blown ornaments and other handmade trinkets. There’s also lantern events and cultural dances and music and all sorts of fun! You gotta get some gluwein and currywurst and gingerbreads with German holiday sayings! You absolutely must buy a Christmas pyramid!

You also must absolutely stand in a line that wraps not only around the city block that takes about 10 minutes, but when you get near the entrance you stand in another, side-wind-y line for another 10 minutes before you can make it in the market itself.

I mean, honestly though the line was not a big deal. There was lots to see and it went impressively fast.

It was the market itself where we lost our steam. SO PACKED. Like, shoulder-to-shoulder packed. We never, ever got near the front of any of the shopping booths.

I mean the kids did appreciate the Krampus booth from the side, though.

We spent a good 15 minutes wandering around about 15 feet from any booth, just clinging to each other (so no one got lost in the sea of shoulder-to-shoulder people) and staring from afar, and slowly weaved our way to the drink booth. Scott and I each got a gluwein, which was honestly a lot tastier than I thought it would be. Also the area around the gluwein area was weirdly less crowded than the rest of the place, so we all just stood there happy to have a breath for a minute and not worry about losing anyone to trampling.

After us adults got a few sips, the kids begged for some hot chocolate so we grabbed tight to each others’ collars again and entered back into the fray to find a hot chocolate vendor. Donermen fit the bill. I stood in that line getting elbows to the face for about 10 minutes, but eventually did emerge victorious with two mugs of hot chocolate.

Then we all took hold of each other again and slowly weaved our way back out, mostly carried by the crowd, chugging our drinks so we could actually leave.

I mean, I appreciated the market? But it was bonkers, sorry. I don’t know if you need to get there during the day as soon as it opens, or what, but I would say at this point: not worth a repeat. Not with kids, anyway. I was glad we got to check it out, but lordy that was too intense to truly appreciate anything. All I wanted was to find a nice, overpriced Christmas pyramid! But I got nothing!

We staggered out, took a few glorious deep breaths, then walked down to Marshall Fields to check out their famous holiday window displays.

(Yes, now a Macy’s. Womp womp sad face, never going to recognize that sorry.)

TipToe the Reindeer was the theme of the year! It was a cute story and fun to check out all the windows.

After that we went on to fulfill Linus’ dream and visit a store he’s been dying to see for at least a year: The Nutella Cafe.

We stood in a line of maybe 6-8 parties in line in front of us. And we stood in line longer than we did for Christkindlmarket. Not even kidding. We just stood there for at least 30 minutes staring longingly into the cafe windows. Totally not creepy to the poor people just trying to enjoy their meal from inside.

Once we got in, though? Totally worth the wait. It’s a Nutella paradise. Nutella everywhere! Nutella merch to purchase! A giant Nutella jar near the door! Nutella treats of all shapes and sizes!

We went simple and got a bag of Nutella shortbreads and ordered their classic crepe.

Lookit that gooey nutella center of these cookies!

That crepe came and you better believe Linus made up an entire song and dance around it while we all just sipped our sodas and let him live his moment of bliss.

At this point: it was getting late and close to a lot of restaurants closing. We made the executive decision to send Scott on ahead of us, to pick up an order from our favorite restaurant before they closed. The boys and I would meet up with him later after the kids finished the Nutella goods.

[Side note: I had to stop him and re-direct the poor guy to get him off in the right direction. Scott is a smart, independent man, but direction is not his strong suit. Which is okay, that’s where I can help (that’s how you pick a spouse, folks).]

ANYWAY. The kids finished their drinks/food and we hugged the giant Nutella jar good-bye a good eight times and then we were off ourselves back to the hotel.

We walked about 15 minutes and then Linus really started taking the piss out of me, he was super concerned that I didn’t know where I was going. WHO AM I, YOUR DAD.

My only regret was walking near Jojo’s Shake Bar, which gets all dressed up for the holidays, and taking a left instead of going on past it and cutting through that light-strung alley. Oh well, next time…

We got back to the room and there was dad, with dinner. Our hero! We had a lovely end to our day: lots of good eats (XOCO never lets us down), plus we watched A Christmas Story from the cozy warmth of our hotel room, with the city shining outside the window.

(Pete gamed from the floor)

Not a bad way to end the night.

Next morning came bright and early! We were also able to take a gander at Rick Bayless’s rooftop garden on top of his restaurants (admittedly, not exactly exciting in the wintertime).

More importantly: I was up early so I walked down and got us some Firecakes treats.

The cranberry-orange glazed old-fashioned! Pretty good, but nothing’s as good as the pistachio, sorry.

After doughnuts we packed up and had one last good-bye to the view, then off we went.

First, to our favorite holiday museum: MSI. We go for the trees, but this year while in line to get our tickets, the boys noticed that the Silver Streak Zephyr in front had opened up as a exhibit (we were only able to view from the outside in the past). So we checked out all the train cars, it’s a great hands-on exhibit now.

After getting through the train and finding dad, we went on to check out the trees.

Then the rest of the museum…

(the plane exhibit also got a cool refresh over COVID-times!)

After we wore ourselves out at the museum, it was off to have a late lunch at our beloved, Rev Brew.

Pete stole my sandwich because he didn’t like his burger, wah.

Then off to home! Actually we stopped in Janesville for some adventuring, but that’s not going here so instead you get some nice winter sunset.

Market insanity aside (NEVER AGAIN), it was a fun trip and I look forward to next year, we’ll explore even more. There’s so much to do, like the Music Box Sing-Along and the holiday train and the Zoo lights and the Walnut Room… I guess we’ll see what next year brings 🙂