Chicago’s Best Steak Restaurants for Valentine’s Day

Nothing says “celebrate!” like a big juicy steak. On Valentine’s Day, the annual celebration of love, a steak is many times what you want to see on your table. Or maybe a lobster. Or probably both.


Valentine’s Day is when many of Chicago’s best steakhouses roll out the big Valentine-red carpet for those in love… or even those who hope to be. There are special menus, special drinks and special treatment for any couple looking to do something a little out of the ordinary for Valentine’s Day.


Here are ten Chicago steakhouses that are doing something a little different for Valentine’s Day, and, yes, there will be lots of red meat involved. And lobster.


Perry's Steakhouse and Grille


Perry’s Steakhouse and Grille. Starting out as Perry’s Butcher Shop and Deli in Southeast Houston, what’s now called Perry’s Steakhouse and Grille maintains its close connection to the source of its success: carefully curated and butchered red meat. On the menu for Valentine’s Day are some of Perry’s greatest hits: Perry filet, prime New York strip and prime ribeye steaks. The folks at Perry’s Steakhouse and Grille know their steak, and just how to cook it to make you very happy.


Truluck’s Seafood, Steak and Crab House. Whether you’re coming for the seafood, steak or crab, you’ll find the best versions of what you’re looking for at Truluck’s Seafood, Steak and Crab House. For the special day, they’re rolling out some special menu items, including Lobscargot (lobster cooked in the traditional herb butter), pan-seared Japanese Hokkaido scallops and a cocktail called TruLuv with dry ice smoke, vodka and Chambord. Don’t let indecision create awkward moments on Valentine’s Day. III Forks makes it easier than ever to order dinner with a pre-fixe menu that includes all the holiday favorites: lobster bisque, cold water lobster tail, filet mignon and chocolate ganache cake. To drink, III Forks has some innovative mixological miracles as well as a beautiful collection of wines and after-dinner drinks.


Harry Caray’s Italian Steakhouse & Bar. Holy cow, Harry Caray’s Italian Steakhouse & Bar knows how to throw a Valentine’s Day bash. Not many people know that Harry was an Italian-American, and that heritage shows in the V-Day dinner that includes lots of choices like toasted ravioli, Italian wedding soup, chicken Vesuvio, and Italian sausage and peppers. Whatever you end up ordering, take our word for it: you want to get a side of Harry’s house-made potato chips: the best.


Ruth’s Chris Steak House. Ruth’s Chris Steak House is synonymous with some of the finest beefsteak in Chicago. On Valentine’s Day, this iconic steakhouse is serving up a love potion of a holiday menu, starring a 40-ounce porterhouse steak for two, with a choice of salads and sides. You can share your love later; at Ruth’s Chris Steak House, start by sharing this big beautiful steak.


The Palm Restaurant


The Palm Restaurant. You believe you and your significant other are a perfect pair? Well then, The Palm Restaurant has a perfect pair just for you, and it’s one it’d be very difficult to top: surf and turf. The Palm Restaurant’s Valentine’s Day menu is going to make you two feel just great with Champagne, as will their somewhat-unexpected though totally delicious offerings like shrimp Bruno (love that mustard), pear salad and a four-pound Nova Scotia lobster alongside an eighteen-ounce prime New York strip.


Ditka’s. You might not think of Ditka’s as the place for a romantic Valentine’s Day dinner, but on the big day, you would be proven wrong to think that way. With a Valentine’s Dinner for Two, Ditka’s features opening salvos of greenery like Mike’s as well as Caesar’s salads, and signature selections like Kick-Ass Paddle Steak and a killer combo: half-back filet and lobster tail. Whatever options you select, there’s a glass of bubbly for you into the deal.


Chicago Firehouse Restaurant. In a beautifully restored old-time firehouse, the Chicago Firehouse Restaurant serves some deliciousness to heat up your Valentine’s Day. You can start with dishes like oven roasted oysters or a wedge salad, and then you’re presented with your choice of seared scallops or lamb lollipops. For the climax: braised beef short rib, European seabass, or prime ribeye steak Diane for two.


Chicago Firehouse Restaurant


About Last Knife. About Last Knife is featuring its regular menu for Valentine’s Day (perhaps with a few surprises), but you really couldn’t want anything more. The beef Wellington is renown in Chicago, but we also like the Ora King salmon, and there are many other wonderful items on the menu that will help make this one of the most special Valentine’s Day dinners. Ever. And the restaurant is well-located on Michigan Avenue, so after dinner, you can enjoy a post-prandial stroll along Chicago’s most romantic street.


Rosebud Steakhouse Chicago. For Valentine’s Day dinner at Rosebud Steakhouse in Chicago, you can start with two glasses of Rosebud Rosé before moving in to heart-shaped ravioli, then sea bass in lobster sauce, and a trio of filet medallions. This memorable dinner ends end with a Valentino turnchetto (but you’re not really ending the evening with dinner, are you?)


Chicago Chop House. Chicago Chop House is one of the coziest restaurants in the city, with low lights, comfortable booths and live piano music. For Valentine’s Day, they’re sending out a complimentary passion fruit pie (get it?) and for the big day you can score (pardon the expression) a bottle of Moet for just $50  – that is a deal on traditional Valentine’s Day bubbly that you’ll not find anywhere else. As an extra complimentary Valentine's Day gift to all Chicago Chop House guests, there's a Chop House Chariot that can take you to and from the restaurant anywhere within a 2 mile radius.


Fleming’s Prime Steakhouse. Fleming’s Prime Steakhouse is known for having the very best steak and wine collection in Chicago, and on Valentine’s Day, they’re outdoing themselves with a remarkably creative menu that will definitely please you and your significant other. Warm up with a crab/caviar blini, and have a pear/pomegranate salad before getting serious with a range of filet and lobster options before you finish up with a New York cheesecake. Of course, there are also some special Valentine’s Day cocktails and flights to get you both in the, ahem, right mood.



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