Worth The Splurge
in Chicago

My take: This is one of the more unique dinner experiences in Chicago as there are only ten seats in the whole restaurant. The meal is a 15-course nigiri omakase. The sushi here runs traditional and the rice is cooked perfectly. Every bite has an insane amount of flavor. You get two-plus hours at a counter where the conversation with the chef gets more personal as the night goes on. We went on a Sunday and had the pleasure of meeting and talking to Otto as he was the head Chef that day. Book 2-3 months out.

My take: Fioretta is a vibe. The room is all checkered marble floors, velvet booths, bartenders in waistcoats, and live music on weekends, a 1950s supper club energy. The kitchen runs Italian-American steakhouse. I have been here 3 times and usually frequent towards the meatballs, shellfish tower, black truffle agnolotti, and the filet. Fioretta sits right in the heart of the West Loop/Fulton Market area, so after dinner you can go out for a night cap depending on how you are feeling.

My take: Galit might be the best-value date night on this whole list, but it can still get a bit pricy if you want to order multiple dishes per category. They pull Midwestern farm produce through a Middle Eastern lens, and it's a tapas style dinner so you get to try everything ordered. You cannot go wrong with anything on this menu and the standouts for me are the brisket hummus, Iraqi kubbeh halab, and the walleye. Galit is right by the corner of Lincoln and Halsted, so after dinner there are plenty of bars around the area to get a night cap.

My take: Maple & Ash is my personal favorite steakhouse in Chicago. The room is dark and stylish, with a buzzing bar and a DJ keeping things going late. They have their signature tasting menu "I Don't Give a F*@k" which I don't think I need to explain, but they bring out their best dishes and you don't have to make a decision. Well worth it. There is nothing in this menu that is bad. This is a splurge in every sense, so come hungry, come thirsty, and don't look too hard at the bill.

My take: Swift & Sons sits right in Fulton Market, the old meatpacking district where Chicago's steak reputation was built, and it leans into that history hard. I have been here more times than I can count, it is a classic in Chicago, but not as mainstream as some of the other big names. The kitchen serves USDA Prime beef seared at high heat with a trio of sauces. There's a magician and a bar cart that work the dining room Tuesday through Saturday, and a dessert trolley every night. Get the Australian wagyu with the king crab Oscar, and leave room for dessert. Fulton Market is a lively area at all times so go wander out after dinner and enjoy the bar scene.

My take: Adalina Prime is the newest name on this list. This one could fit in all my categories but it is technically a steakhouse, with cathedral ceilings and curved wooden beams. The steak program spans Illinois-raised Miller Ranch Wagyu plus Japanese and Australian cuts, and there's an interactive Salt Library with close to a dozen flavor pairings to season your cut. The cocktail program leans hard into martinis. If you are looking for a fun experience, get the tableside martini.

My take: Trendy is Tre Dita and you will notice that right when you walk in. It sits on the second floor of the St. Regis Chicago with 40-foot windows looking out over the river, Lake Michigan, and Navy Pier. The kitchen is Tuscan and it runs around a wood-fired grill and a temperature-controlled pasta lab you walk past on the way in. They have an amazing steak selection and all their pasta is handmade. Bar Tre Dita next door for a drink before or after dinner.

My take: Alpana is the move when the night is really about the wine and food pairings. It comes from Master Sommelier Alpana Singh, and the whole place is built around the glass, with every dish designed to make a specific wine taste better. The room leans into a wild, strong energy, with over-the-top florals, chandeliers, and a wall of portraits. The food is globally-inspired bistro fare meant for pairing and it is a lively, see-and-be-seen Gold Coast room. Sit at the bar if you want the full sommelier treatment. If you are looking for a drink after there is a speakeasy a couple blocks away called Rose Lounge.

My take: Miru sits eleven floors up in the St. Regis Chicago and the dining room and two outdoor terraces look out over Lake Michigan, Navy Pier, and the river. The food is modern Japanese: a 12-seat sushi bar, sharable plates, tempura, crispy rice, and wagyu. If you want the real experience, the Wednesday bluefin tuna tasting walks you through the cuts from lean to fatty and ends with their signature Miru-Ishi dessert. Ask for the fresh wasabi and they will come out and grate it in front of you.