Chicago’s the Fifty/50 Group has so far been known for their eclecticism with restaurants ranging from the namesake sports bar to Roots Handmade Pizza to craft cocktail lounges like the Berkshire Room. With the recent opening of Steadfast in the Loop’s business district, the Fifty/50 Group has gone to the next level with a fine dining concept that blends Mediterranean and Portuguese flavors into classic dishes, served with a stunning presentation.

The Space

Steadfast sits at the front of the New York Life Insurance building at 120 W. Monroe Street. Designed by William Le Baron Jenny and built in 1898 as an office building; the New York Life Insurance Building is a prime example of Chicago School high-rise construction that followed in the decades after the Great Chicago Fire. In the mid-2000s, there were plans to tear down the 14-story building for a 51-story high rise, but fortunately the city designated the building a historical landmark in 2006. Now the building has been converted to the brand-new Kimpton Gray hotel.

As fitting for the historical setting, the restaurant is immaculately designed– mixing both classic elements like marble table tops along with rich woods so the restaurant feels more alive and not like a relic. There’s a small patio out front, while the 104-seat interior has several unique spaces that offer very different dining experiences ranging from an all-marble private dining space to the back area with an open performance kitchen that adds an extra level of entertainment to the evening (surprisingly it’s not that noisy). Of course, the fastidiously ornate bar, with cocktails crafted by Benjamin Schiller, is the perfect place to come for a lively happy hour drink after a day at the office and feel like you’re the boss.

What to Order

Steadfast divides their menu into snacks, medium, large, and for the table portions so there’s a little something for every type of diner whether you’re just grabbing a quick bite at the bar after work or the entire family has gathered to celebrate a special occasion. While everything I sampled was extraordinary and beautiful to look at, these were a few of my favorites.

Take a look near the kitchen and you’ll see a window of meats gently hanging and aging to be served much later as part of Steadfast’s charcuterie menu—all prepared in house. A nine month-aged prosciutto was exceptional, while my favorite was a coffee-cured lomo topped with fried chicken skin that tasted like the best bacon you’ve ever had x 10.

To go along with your charcuterie, why not order a side of bread? Steadfast freshly bakes a cornucopia of breads served with an even more impressive array of butters and spreads like a creamy and sweet honey butter and an eye-popping violet cauliflower that looks like an Instagram filter in real life.

I’ve been on a role lately with great kale salads, and the Wood Grilled Kale salad at Steadfast is a new favorite. Unlike most salads, this is served hot with the kale grilled to a point where it’s warm and a little crunchy– yet not quite a kale chip. It’s then topped with bacon vinaigrette, which is as amazing as it sounds, smoked and gooey goat cheese, Sumac candied pecans, and compressed pear. Like the foie, there’s a diverse blend of flavors and textures here that all come together, while also remaining equally distinct to create a salad that’s equally savory goodness, sweet reward, and healthy starter.

The presentation of everything was stunning, but seeing a fleet of perfectly arranged shells coming your way is a wonderful thing. Great for sharing with a group, the mussels are served in a Calvados cream sauce with Sumac apples. The apples provide a sweetness that covers any “fishiness” of the tender mussels. What I really like about Steadfast is how they have these dishes we’re all familiar with yet the flavor patterns are never quite what you expect.

In the “For the Table” category, the lobster is a truly decadent dish. In addition to the fresh lobster in a lobster & uni emulsion sauce, there’s a piece of buttery brioche topped with caviar and coffee-roasted potatoes that are probably unlike any sort of potato you’ve had before. Most people would be fine with just eating a lobster on its own, but I loved how Steadfast created this really unique flavor world with this dish. And while I’m certainly repeating myself, the dish itself looks incredible.

And to finish the evening, here’s a whole duck for you. Though the price of $75 may first cause you to gasp as you look at the menu, this is a big piece of meat that will set the scene at any special occasion dinner. Dry aged for seven days and covered in a light lavender honey glaze, the duck is amazingly tender and seems to lovingly disappear and fade away in your mouth (certainly the best duck I’ve had so far in my life).

Bottom Line

The business district downtown used to feel abandoned after the workday was over, but Steadfast is reason enough to stick around or venture out for dinner. With their new concept, the Fifty/50 Group has outdone themselves with a beautifully decorated space and incredible-looking dishes that blend classics with unexpected, complimentary flavors. Steadfast is certainly the best new restaurant I’ve tried this year.

Steadfast Chicago
120 W Monroe St, Chicago, IL 60603
(312) 801-8899


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