Best Chicago Steakhouses for a Helluva Holiday Dinner

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Roasted seafood at Maple & Ash

As we move into the holiday season in Chicago, here are a few steakhouses that have opened relatively recently – and one exceptional classic – that have generated a lot of buzz. You have a special date or family get-together planned for the holidays? Here are some of the truly exceptional places you might want to go for a helluva holiday dinner.

Beef Wellington at Mason Steakhouse

Beef Wellington at Mason Steakhouse

Mason Steakhouse. Updating the All-American – and distinctly Midwestern – supper club tradition, Mason has a retro-menu of cocktails and entrées that will make you feel like you stepped into Chicago in the Forties or Fifties. Daquiris, old fashioneds, negronis – all made with top-shelf liquors – get the party started, and it’s great to see some popular standards make a re-appearance on Chicago menus: Beef Wellington (carved tableside) and Dover Sole are just two of the classics that will knock your socks off.


Steak 48. One of the newer additions to the Chicago steakhouse scene, Steak 48 is sleek and swank, and the menu is full of some of the best red meat you will ever see. There’s domestic Wagyu N.Y. strip and filet, but get this: steaks are wet-aged for 28 days, custom-cut to preference in the on-site butcher shop that’s always set at 40 degrees (not freezing, but cold enough to keep the meat super fresh), then sizzled under a 1800 degree broiler for a super char. You’ll have a very hard time finding steak this good, anywhere. Mind-blowing.


Truluck’s Seafood Steak & Crab House. Recently arrived in Chicago, Truluck’s Seafood, Steak & Crab House is a branch of a well-regarded national restaurant group, and it’s the rare instance of a place that gives almost exactly equal attention to seafood and steak. The seafood, fresh and flown in daily, can be enjoyed cold or hot, and the steak is prime and served on a 500 degree plate so that it stays comfortably warm while you eat it. Or, you can have seafood and steak, together, on dishes like the Filet Oscar Royal, a perfectly prepared filet topped with crab and caviar, the best of both worlds, the terrestrial and the aquatic. You will love it.

Roasted seafood at Maple & Ash


Maple & Ash. If you happen to be shopping along the Magnificent Mile this holiday season, you will not find a more sophisticated place for steak than Maple & Ash. Wood-roasting, lending the perfect smoky flavor to winter meals, is used for both seafood and steak  and even the French onion soup! There’s a range of seafood towers, and Snake River Wagyu strips and filets head up the list of truly exceptional red meat options.  For lighter appetites, there’s a range of caviar, just right for a holiday celebration. Superb.


Gene & Georgetti. The godfather of all Chicago steakhouses, Gene & Georgetti is the iconic Italian-American restaurant that makes many of the others seem like mere upstarts. In a wood frame building, one of the few left standing in downtown Chicago after the Great Fire of 1871, you’re welcomed into a cocktail lounge that opens onto a few floors of dining. After having a martini at the bar (hey, it’s tradition!), sink into a classic steak like a t-bone or porterhouse, and try to imagine what this place must have looked like when it opened in 1941 (hint: it probably looked a lot like it does today).


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