Confession: I’ve never truly celebrated Christmas before. Sure, I’ve seen the odd Christmas movie, and I’ve heard “All I Want For Christmas Is You” one too many times just like the rest of us. But my experience with the world’s favourite holiday ends there.
So since I didn’t grow up with Christmas, I’ve always seen holiday trips as just a way to escape cold, snowy Toronto and get some vitamin D. But when I got the chance to join a group holiday trip to Chicago, I decided I couldn’t say no, and ditched the beach vacay for a Christmas extravaganza.
So as a first-timer to both Chicago and Christmas, I’m gonna give you my brutally honest recap. Was it worth it? What surprised me the most? Let’s get into it.
1.
Let me start by saying this: Chicago absolutely goes OFF for the Christmas season. For one, the entire city gathers for a huge tree lighting ceremony every year — which is too wholesome for words — and I can’t even tell you how many places I saw completely decked out in ways I’ve never seen in literally any other city (yes, including Toronto and New York). This one pop-up bar, Santa Baby, was three floors plus a patio of Christmas mania, and it was the most warm and cozy atmosphere ever.
2.
I’ve been lucky enough to visit Christmas markets all around Europe, so I was stoked to find out Chicago had one, too. And it’s not just an average Christmas market — it’s an authentic one that completely immerses you in German culture. Of course they had giant pretzels and incredible hot chocolate, but they also had imported German candy, which I thought was so cool. Vibes were on point.
3.
Speaking of, I absolutely cannot talk about Chicago without mentioning the FOOD. Of course, I tried many Chicago classics, starting with deep dish pizza at Lou Malnati’s (a Chicago fave). I was skeptical, since Italian-style pizza will always have my heart, but this was unbelievably delicious. Crunchy, cheesy, and packed a super-fresh tomato sauce, I understand and 100% stand by the hype. Christmas turkey, move aside — deep dish is my new holiday tradition.
4.
But I was also really impressed with the fine dining. AKA, I had the greatest (and potentially the biggest) meal of my life on this trip. It was at Girl & the Goat, and it was packed with tons of decadent meat, chicken, and fish dishes, plus green beans that I will be talking about for AS LONG AS I SHALL LIVE. I know what you’re thinking: How can green beans be so good?! But trust me, that salty, cashew sauce lives in my dreams. I shouldn’t have been too surprised because the restaurant is owned by Stephanie Izard, the first female winner of Top Chef, but still, it blew my mind.
5.
I was already blown away when I learned Chicago has a HUGE Christmas parade EVERY SINGLE YEAR…but when I learned we’d be PART of the parade? I was floored! Picture this: A group of people from around the world, on a float, dancing, waving flags, and screaming “happy holidays” to thousands of Chicagoans. I’m pretty sure we solved world peace on that float, and I haven’t smiled so hard in awhile. Talk about a first Christmas experience!
6.
Some activities that weren’t necessarily holiday-themed had an extra special festive vibe to them that just made my heart happy — decor, music, you get it. And honestly? It convinced me Chicago commits to “the most wonderful time of the year” more than most other cities. Skydeck was one example of this: A super-fun experience where you can stand on the ledge of one of the tallest buildings in North America. The photos I got here are my faves of the entire trip.
7.
But of course, there were many non-Christmassy activities that this trip gave me the perfect opportunity to experience. When I signed for Chicago’s architecture boat tour, I was skeptical, mainly because A) it’s winter, and B) I don’t know anything about architecture. But this tour knocked my socks off — if you’re a fan of history to any degree, this is a must-see. It totally makes sense that this tour was voted the second-best travel experience in the world (number one is a Vatican tour, which I assume is fair).
8.
I know many people think of New York when they picture a winter holiday vacay, but as it turns out, Chicago has my two favourite things about New York: amazing shopping, and Broadway shows. Yes, Broadway in Chicago is a thing! And as a huge fan of musicals, I’m telling you: the production quality is top-notch. We saw Hell’s Kitchen, but I was super jealous to find out one of my favourite Broadway shows, Water for Elephants, is coming soon.
9.
Finally, yes, I’m saving the best for last. My biggest surprise of the entire trip, the most underrated gem, and the thing I’d absolutely book an entire trip around is the Chicago Magic Lounge. Hear me out. It’s a stunning, vintage speakeasy with daily performances from globally acclaimed magicians (not to mention great food and cocktails). Following the show, I literally exclaimed, “This reminds me life is worth living!” — dramatic, but I totally stand by it. I lived on a complete high for many days afterward, and it’s absolutely a core memory.
So, in short, is it worth flying to Chicago for the holiday season? ABSOLUTELY. And that’s coming from a Jewish gal who loves beach getaways. I thought my seasonal depression could only be cured by sunshine, but it turns out a good ol’ holiday vacay can do the exact same.
What’s your fave underrated vacation spot? Tell me in the comments below, because you know I’m always looking for recs!
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