Chicago: A Christmas Weekend in the Windy City

Way back when I lived in Madison, going to Chicago for the big Christmas market was an annual thing. I always loved it – I am, of course, a sucker for a good Christmas market – but it occurred to me last year that it had been something like eight years since I last visited. So, of course, I had to remedy that! It was a cold and drizzly weekend but, even so, still wonderful to see the city decked out for Christmas.

I began with breakfast at Little Goat Diner, which included one seriously delish cinnamon roll (one of the best things I ate last year, in fact). Honestly, it took all my willpower not to go back the next day and just order the same thing again.

After breakfast, it was off to the main event: the Christkindlmarket. I already have way too many ornaments for my tree, but I just … have no restraint. I bought several German glass ornaments, plus a new nutcracker and some Santa Claus matryoshka dolls for good measure. Sorry not sorry, I guess!

From the market, I walked up Michigan Avenue to admire all the Christmas decorations there. I always love taking a peek at the Macy’s windows, in particular.

For lunch, I stopped into Frontera Grill. I’ve been to other Rick Bayless restaurants, but somehow had always missed this one, so it was nice to check it off finally. Love a good tortilla soup.

After lunch, I did yet more Christmas shopping. The clear highlight was P.O.S.H., which has long been one of my favorite stores. It has the loveliest mix of vintage and French-inspired treasures. I literally want to buy ALL the things every time I go.

In the evening, I dined at Spiaggia, another restaurant that’s long been on my Chicago bucket list. I opted for the tasting menu, which was a LOT of food, but all quite good. The bucatini and tortellini in particular were favorites.

The next morning, the weather turned even MORE rainy and frigid, so I let myself indulge in a slow, lazy morning. After grabbing brunch, I made my way to the Bean. Nearby, I found the city’s gigantic Christmas tree. Big finish!

Due to an impending snowstorm, I wound up catching an earlier flight back home. So, it was an all too short weekend, but definitely worth it to get my Christmas fix, however brief.

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