Date night in Chicago’s Fulton Market District offers no shortage of exciting restaurants and cocktail destinations. On a recent evening out, my husband and I decided to check two spots off our list: dinner at
Rose Mary followed by cocktails and small bites at
The Office.
The result? A night of bold flavors, mixed impressions, and one truly unforgettable cocktail experience.
Dinner at Rose Mary
Rose Mary had been on our radar since opening, so we were excited to finally book a reservation. The restaurant showcases the culinary vision of chef Joe Flamm, blending flavors inspired by his Italian heritage with Croatian cuisine.
We had an early reservation, and the dining room was fairly quiet when we arrived. I was a bit surprised when we were seated at a two-top table with a rather intrusive structural beam pressed against my chair. My husband was given a menu by our server while I scanned the QR code on the table.
Not the most romantic start to date night, but we were hopeful the food would steal the spotlight.
Standout Starter: Zucchini Fritters
We began with the zucchini fritters, dusted with a fragrant spice blend and served with an herbaceous pesto aioli.
These were easily one of the highlights of the meal — crispy, light, and packed with flavor. If you’re visiting Rose Mary, this is definitely a dish worth ordering.
A Few Missed Notes
Next came the Chitarra pasta with truffle. As someone who absolutely loves anything with truffle, I was especially excited for this dish.
Unfortunately, it was just okay. The flavors felt muted, the pasta was a bit too al dente, and it didn’t deliver the richness I expected.
I was even more eager to try the Sarma — stuffed cabbage — a dish I grew up eating thanks to my Serbian grandparents. It’s a nostalgic comfort food that appeared on our family table at nearly every holiday.
The tomato-based sauce was nicely balanced, but the cabbage itself was undercooked, and the awkward table setup made it difficult to properly cut the dish without repeatedly bumping the beam beside my chair.
At that point, I realized the beam and I simply were not going to coexist peacefully.
Traditional Dishes with Mixed Results
The Cevapcici, another traditional Balkan dish, arrived with excellent house-made ajvar and kaymak.
While the accompaniments were fantastic, the sausages themselves felt dry and lacked the garlic and herbs that typically give the dish its signature flavor.
The Dish That Saved the Evening
Thankfully, the Braised Lamb Shoulder with tomato-braised lentils was exceptional.
Tender, rich, and deeply comforting, the lamb practically melted with each bite. The dish beautifully blended Italian-style comfort food with an Adriatic influence and quickly became the clear star of the meal.
We paired dinner with a Tuscan Cabernet Sauvignon, which complemented the heartier dishes nicely.
Nightcap at The Office
After dinner, we headed to The Office, the intimate cocktail lounge located beneath The Aviary.
If Rose Mary felt lively and modern, The Office immediately transported us into an entirely different atmosphere.
The door remains locked and is opened with a key, adding a subtle speakeasy feel before you even step inside.
An Intimate Cocktail Experience
The 21-seat lounge is dimly lit and designed like an old-world study — plush chairs, leather sofas, dark woods, intriguing artwork, and a warm, inviting ambiance that feels both exclusive and comfortable.
We opted for the tasting menu, which included five cocktails impeccably paired with small bites.
Immediately, the service stood out. Our bartender walked us through each drink in detail, readily answering questions and sharing the story behind each ingredient.
It was thoughtful, engaging, and exactly the level of hospitality you expect from an Alinea Group concept.
A Cocktail Journey
Our first cocktail was a classic Highball made with Aviary’s George Dickel Second Edition Bourbon and Purkhart Pear Brandy. The bottle was presented at the table, encouraging conversation.
It was paired with what may have been the best butternut squash soup I’ve ever tasted — warm with a unique spice blend, velvety, and deeply comforting.
Next came a Truffle-Infused Daiquiri served alongside the famous Black Truffle Explosion. This pairing was playful and indulgent, delivering bold flavor in both the glass and on the plate.
After a short pause, we were served an Old Fashioned with a delicate hint of strawberry that gently perfumed both the nose and palate. This drink was paired with a Kalbi taco made with beef short rib — a delicious bite I savored slowly.
The fourth cocktail was a perfectly executed Barrel-Aged Mezcal Negroni paired with Basque cheesecake topped with a cherry and currant compote. This was a dessert after my own heart as I prefer a dish with balance and a restraint in sweetness.
Finally, we finished with a vintage pour of Cinzano Rosso from the 1970s alongside a plate of petite mignardises — three delicate bites that ended the tasting beautifully.
Final Thoughts
Thankfully, we ended the evening at The Office.
It delivered exactly what we hoped for: warm hospitality, beautifully crafted cocktails, and an intimate experience that felt truly special.
As one of the most sought-after reservations in Chicago, it’s easy to see why. The service was impeccable, the cocktails were imaginative yet refined, and every detail reflected the high standards of the Alinea Group.
Pro Tip
Reservations for The Office are extremely limited and can be difficult to secure.
If you’re looking to spend a special night out in Fulton Market, plan ahead!
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