Editor’s Picks: Best Chicago steakhouses to explore this winter

There’s no better time to discover a cozy, dimly-lit steakhouse than during Chicago’s winter season. From menus stacked with hearty soups, flowing spirits, and the finest cuts of meats, Chicago boasts some of the best steakhouses in the country. In this Editor’s Pick edition, our editors have selected their favorite steakhouses that offer mouthwatering steaks as well as a top-tier ambiance to make wintertime in Chicago seem a whole lot brighter (and tastier).

Gene & Georgetti

"Gene & Georgetti is one of my favorite steakhouses and restaurants in general. Besides the delicious food, I love the fact that they make every single customer feel like family. It’s been family-owned for over 80 years which definitely says something about its popularity and staying power. You always feel like you’re dining in a friend’s home and there’s no better feeling than that. Frank Sinatra loved it too and has his own booth in the back of the front room." - Candace Jordan, Associate Publisher

Smith & Wollensky

"I like Smith & Wollensky the best because of its riverfront dining. Their steaks have a distinctive flavor that is simply not replicated at other steakhouses. You can actually taste the difference between different cuts of meat." - Elaine Hyde, Publisher & Editor

Bazaar Meat

"If you ever find yourself in the Windy City and enjoy upscale dining, you simply MUST visit Bazaar Meat by Michelin-starred Chef José Andrés. This steakhouse truly transcends the idea of sophisticated dining with colorful and inventive dishes that make for a rather intriguing dining experience. Bazaar Meat Chicago sits above Bar Mar and offers spectacular views of the river. The ambiance is quite intimate with red velvet chairs and a massive matching chandelier. Upon entering the steakhouse, meat lovers will find a glass display of huge cuts of meats from different animals. We started with an order of the José’s Tacos, which are not your average tacos. This popular Bazaar Meat Chicago dish comes with two bite-sized pieces. A layer of seaweed is topped with a Spanish ham called jamón ibérico de bellota. A dollop of Ostreta caviar is laid on top with a sprinkle of gold leaf. Aside from the incredibly tender and flavorful steaks, this was perhaps my favorite dish, as it is both chewy and tangy. I ended up getting another order just for myself of these." - Ashlea Hearn, Associate Editor

Gibsons Bar & Steakhouse

"Gibsons Bar & Steakhouse has a special place in my heart since it’s where we announced our engagement. Besides the extensive menu and mile-high desserts, this restaurant is known among locals as the best place for a celebration. Manager Kathy Piccone makes sure everyone is seated where they want and many of the servers have been there since the place opened in 1989. Always at the top of my list! A great spot for celebrity watching too." - Candace Jordan, Associate Publisher

St. Charles Place Steak House

"St. Charles Place Steak House is located on North Avenue in St. Charles, but it is well worth the drive. It is an eclectic mix of elegant and tacky. When you walk in you are immediately taken back to a Sinatra supper club. Everything is red and black, the chairs are classic oak and velvet. The stone floor-to-ceiling fireplace. There are little nooks of private tables everywhere. The bar has a hundred-year-old oak tree growing right in the center. The menu is a mix of classic dishes like duck l'orange complete with a dramatic tableside serving to chateaubriand for two. We went with another couple and had classic dirty martinis and wine and we were there for 3 hours. I think we closed the place down on a Thursday night. The service was top-notch. We didn't feel rushed and the waitress was super fun and attentive to all of our requests. They even accommodate a difficult picky eater without making them feel like they were a burden. The owner is a walking version of his restaurant. He is a mix of old Capone Chicago, but when it comes to his menu, you feel like you are talking to Gordon Ramsey. Just a cool, old-fashioned quaint supper club. No jeans though - you will definitely feel out of place if you aren't dressed business casual. Not a single person was wearing jeans or a t-shirt." - Annalisa Wilson, Contributing Writer

Gibsons Italia

"I really like Gibsons Italia. I love the decor; it’s simple but elegant, and the view of the river is beautiful. But my favorite part is the memories I made there celebrating New Year with my family and going out with friends."  - Amina Sergazina, Contributing Writer

Chicago Cut Steakhouse

"Chicago Cut Steakhouse has two of the best owners in town, Matt Moore and David Flom. This two-level temple of fine dining also has the best location, right on the river. Their prime, dry-aged beef and iPad wine list will make you weep tears of foodie joy." - Candace Jordan, Associate Publisher

La Grande Boucherie

“La Grande Boucherie is one of Chicago’s newest and hottest restaurants and easily became one of my favorites! This traditional French steakhouse and brasserie opened its doors in the Belle Époque building in River North. And all I can say is WOW, what an experience! The dining room feels cozy for such a lively place. When we attended the grand opening, the jazz band really added to the ambiance. The most impressive thing I saw from their Les Grands Formats part of the menu was the confit de cochon de lait; this is a whole confit suckling pig served with red cabbage and roasted apples. It took two waiters to carry this baby on an enormous silver platter!” - Ashlea Hearn, Associate Editor

Chicago Firehouse Restaurant

"My second favorite is the Chicago Firehouse Restaurant. We went for a birthday party upstairs in the parlor room and it was so quaint. The food was awesome! The filet mignon was tender and the sauce was the perfect compliment. The second time we went was for a date night and we sat on the veranda and again, it did not disappoint. I had a dirty martini (perfect!) and for dinner a delmonico ribeye with roasted bone marrow and I did not know if I should have eaten the dinner or taken it to a room to be alone with it. The service was good, nothing to write home about but the food was memorable. Side note: My daughter Michaela ordered the oysters and she said they were perfect. She has become a somewhat oyster fanatic and orders them whenever they are on the menu." - Annalisa Wilson, Contributing Writer