I am so thrilled to report that Chicago is back on the map as far as absolutely superb Italian-inspired restaurants go. After several disappointing meals at very popular spots like Il Carciofo and RPM Italian, I was starting to worry I’d never find good Italian food in the city again. Then, I had dinner at Daisies, which was a revelation, and I reviewed it here, and hope for amazing pasta in Chicago returned. Finally, most recently on Thanksgiving weekend, we enjoyed a birthday celebration dinner at Tre Dita, located in the immaculate St. Regis Hotel, Chicago.

Tre Dita only opens reservations to the public two weeks out, so you’ll have to jump quickly to get a table at this incredibly popular spot. Luckily, since we were staying at the St. Regis for a night, their butler service hooked me up with a prime reservation before they were even open to the public. The restaurant is located on the second floor of the hotel, with river views, although when it’s dark, you’re not really there for the view, you’re there for the hip-yet-cozy ambiance of the restaurant. With soaring lofted ceilings, this is a very open space, but feels intimate since it’s lit quite darkly, and the tables, while not jammed, are somewhat close together. It’s a lively space, and feels special when you walk in.

Service here was excellent, and the Sommelier was super helpful with choosing a wine we would love. I knew the basics of what I was looking for, but since I wasn’t familiar with many of the producers, he was a big help. Their Italian wine list is truly spectacular, with a dizzying array of wines from every region of Italy, making choices tough. Don’t ever hesitate to ask questions, the table next to us was receiving a master class in Tuscan wines during their meal!

The food at Tre Dita is extraordinary, and really highlights what you can do with hand-made pasta using high quality ingredients. They import their flour from Italy, and make all the pasta in house, and you can tell that it’s fresh. Honestly, I forgot that pasta itself can actually be flavorful when made fresh and with care, and I was delighted to be reminded of that. We started with focaccia, which was fluffy to the extreme, and just the right amount of oil such that butter or other dipping condiments were rendered completely unnecessary.

Following this, we had fried squash blossoms stuffed with ricotta. These were lightly fried, delicate, and not too greasy. I don’t know where they are getting fresh squash blossoms in December, but this is easily one of my favorite antipasti on the planet. A drizzle of crushed fennel seeds and other spices really elevated this dish.

Next up we tried the special pasta dish, which was Cappelloni Alla Senese. When we ate here, it was a special, but it has since been added to the regular menu due to its popularity. This dish was a revelation in stuffed pastas. The delicate pasta is stuffed with short rib, ricotta, and spices, and it’s glazed with a lamb reduction. Not only was the short rib and ricotta stuffing extremely flavorful, but the pasta itself was delicious, adding a lovely layer of flavor normally absent in lesser-quality preparations. This dish was easily one of my favorites of the entire year.

We also ordered the oxtail ragu, which was amazing, though slightly overshadowed by the previous dish. Again, though, the pasta itself was obviously fresh and delicate, yet firm and al dente, and the sauce was not too gloppy or overbearing. A really nice dish. Note that the portions are quite generous. Each of these pasta dishes was probably enough for the entire meal.

Since this was a special occasion, we also splurged on the 60 day dry aged 32 ounce bone-in ribeye, which came with the most amazing smashed fried potatoes and an arugula salad. While I can’t say this was my favorite steak in Chicago (that’s still at Bavette’s), it was definitely prepared perfectly and was super flavorful. I think they overdid it on the seasonings including lots of fennel seed on the steak itself. I’ve always said that a good steak needs nothing but salt, pepper, and a little bit of butter, if the meat is high quality, which this was. That said, the potatoes were absolutely perfect – small, smashed and very slightly crispy on the edges, and seasoned simply with salt and pepper.

Following our main course, we had a tough time deciding on dessert drinks, but landed on our current favorite digestif, Chartreuse, of which they have several varieties. Brian was brought a cute, complimentary bite of tiramisu for his birthday, and we also ordered a slice of the pistachio cake. Without even knowing it, this dessert is gluten free, since it’s made out of pistachio flour, and I can’t even imagine how expensive that is. The cake itself was decadent, but not too rich, nutty, and maybe one of my favorite desserts of the year as well. It definitely rivals the pistachio cake at San Morello in Detroit, a slice of heaven that, nearly three years later, still claims a piece of my heart. I was happy to find a comparable dessert here in Chicago!

If you can snag a reservation, don’t hesitate to book at Tre Dita. If you stick with the pastas (which would be totally reasonable!), your experience here doesn’t even have to break the bank, since the prices are very reasonable for the quality of cooking. I absolutely loved our experience here, am dreaming about returning for more pistachio cake and pasta, and am making room on my Top Five list for 2025 for this lovely restaurant.