4 Charles Prime Rib
4 Charles St.
Steak House $$$$
Resy 29 days in advance
4 Charles doesn’t give out reservations at normal times. Normal being, you don’t want to eat with you grandparents at 5pm and you’re not trying to sweat out a 16 oz prime rib and half a cheeseburger into the wee hours of the morning.
The 7-8:30pm reservation is rarely every available (on Resy) even if you’re staying up until midnight 29 days in advance, so don’t expect it. My recommendation is to either 1) Set a notification on Resy for a certain time you’d like to eat, put your email notifications on, and be on your phone 24-48 hours in advance in hopes of a cancellation (which usually there are) or 2) Try walking in and putting your name in (preferably not on a Thursday – Saturday) and see if they have any cancellations (they’ll text you).
The meal itself is spectacular (from the service to the atmosphere to the food) and I’ll give you my unsolicited opinion (even though it won’t be that different from what you’ve already heard). Drink wise, I like the cocktail play before ordering wine for the table. They specialize in martinis – it doesn’t matter if you don’t like martinis, tonight you do. Yep, they are expensive – get over it. The cheeseburger (now my favorite in the city) is almost too big for two people to split considering it’s used as an appetizer but nonetheless will be ordered. There’s controversy over going normal or adding bacon or adding an egg or doing all three. Order the bacon – how much meat is too much meat? As far as the steaks go, we ordered the Chicago Cut (the mid-price point of the three), which was a 16 oz. center cut compared to the English Cut (which is thinly sliced and 10 oz.), which I would highly recommend. Note, they do have limited availability of that and the French dip (off menu and usually only ~10 per night). For sides, we ordered the button mushrooms and the truffle mac (a special) and that was PLENTY. In my opinion, you could tack on another side and appetizer, and that would have been enough for four people.
It’s intimate, it’s sexy, and it’s damn good. Go to 4 Charles with someone or some people who will appreciate a waiter putting on gloves to cut their cheeseburger, who are down to throw down, and don’t mind having the entire meal focused on meat.