January in Chicago felt like the perfect kind of winter getaway — crisp, cinematic, and full of cozy indoor moments balanced with just enough time braving the cold.
One of the highlights of the trip was seeing Harry Potter and the Cursed Child at the Nederlander Theatre. I really enjoyed this one! The way the stage felt like it was moving actually felt like magic. ✨
I also went to a Blackhawks game versus the Tampa Bay Lightning — two of my favorite teams, which made it even more fun to watch. The energy in the United Center was incredible, especially with that classic Chicago winter backdrop outside. As an avid hockey watcher, I love being in person and really feeling like you've got something on the line. Unfortunately, the Blackhawks lost, but it was still fun — and cold. Earlier that day, I also stopped at the Blackhawks official store and grabbed some merch!
One of my favorite parts of visiting Chicago is that my best friend lives there, so we were able to meet up a few times throughout the trip. One of those meet-ups was at Ralph’s Coffee inside the Ralph Lauren store on North Michigan Avenue and East Chicago Avenue — such a cozy little spot to escape the cold and catch up.
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| Famous folks who have stayed at the historical hotel, The Drake |
I stayed at The Drake, which felt especially fitting for a winter stay in the city. Mornings there were slow and indulgent, often starting with breakfast nearby. I had some really good meals that week, including avocado toast from Chapel Street Café and a classic everything breakfast at Wildberry Pancakes & Café — both perfect fuel for long days exploring the city.
Of course, no Chicago trip feels complete without a visit to a museum. I visited The Art Institute of Chicago. It’s massive, and every time I go, I feel like I’ve only scratched the surface. I could wander there for hours and still discover something new.
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| I always end up loving the Italian art the most. |
I also made time for a little coffee tour, which felt essential given how many great coffee spots Chicago has — from local favorites to well-known chains. I finally stopped into Blue Bottle Coffee for the first time after visiting other cities like New York, and it quickly became a standout. There’s something about their coffee that just feels consistently elevated and worth the stop.
One thing to know about visiting Chicago in January: it is cold — truly Windy City cold. Lake Michigan was completely frozen over during my visit, and bundling up is non-negotiable. That said, there’s a quiet charm to the city this time of year. Fewer crowds, cozy interiors, and a slower pace make it surprisingly enjoyable, as long as you dress for the weather.
Chicago in winter is bold, a little bracing, and absolutely worth it — especially when you get to experience it with good food, good coffee, and good company.
What should I do next in Chicago?
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