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Love is in the air, and there’s no better way to show loved ones how much they mean than with a delicious meal. This Valentine’s Day, treat that someone special to an exceptional night out at one of Chicago’s top restaurants, pamper them with a trip to the spa or opt for something a bit more interactive – the options are endless. 

Benny's Chop House (444 N. Wabash)

The independently-owned River North steakhouse offers diners the an array of menu offerings. The Sundae for Two, designed for guests to share, is a Chocolate-dipped bowl with salted caramel pearls, butterscotch chips, and white sprinkles, served over warm brownies and 3 scoops of ice cream with banana rum, strawberry, almond coffee toffee, and topped with served with whipped cream and Bourbon-Caramel Sauce. From February 14-16, the restaurant will offer an array of  menu specials in addition to the full dinner menu.  


Wicker Park – 1566 N. Damen 

West Loop – 161 N. Sangamon

Just in time for Valentine’s Day, Bonci is debuting its first-ever dessert pizza - a combination of Nutella, strawberries, toasted marshmallows and a touch of mint. 

Eden (1748 W. Lake St. )

Eden, the new American restaurant by husband and wife duo Jodi Fyfe and Executive Chef/Partner Devon Quinn is celebrating Valentine’ s Day with two prix fixe menus, including a vegetarian option. Chef Quinn will be using ingredients straight from the on-site garden on both menus with dishes including Fjord Sea Trout Crudo (Salsify, Grapefruit, Buttermilk, Pistachio, Smoked Trout Roe, Basil, Dill), Painted Hills Fillet (Beluga Lentils, Sunchoke, Wild Mushroom, Tarragon), Ricotta Herb Gnocchi (Carrot, Wild Mushroom, Cultured Butter, Lemon Verbena) and Curried Lentil Brik (Beet, Chèvre, Cauliflower, Swiss chard, Chermoula, Puffed Grains). For dessert, guests will be able to indulge in a Chocolate Peppermint (Devil’s Food Cake, Peppermint, Branca Menta) to finish off the meal. The regular tasting menu will be available for $150 per person and the vegetarian tasting menu will be $110 per person. Both menus offer the option for wine pairings for an additional $50. 

Entente (700 N. Sedgwick St.)

Michelin-starred restaurant Entente is offering a special Valentine’s Day weekend with a choice of two tasting menus available Friday, February 14 through Sunday, February 16. Guests can choose from an eight-course menu for $185 or a 12-course menu for $245 curated by Executive Chef Brian Fisher and Pastry Chef Jared Bacheller. 

The Florentine (151 W. Adams)

From February 14 through the weekend, The Florentine will offer an array of romantic specials in addition to the regular menu offerings  Guests will be offered Executive Chef Zachary Walrath’s dishes such as the nightly rotating risotto, house made pastas, Branzino and other Italian specialties. 

Gene & Georgetti Rosemont (9421 Higgins Rd.)

While the Chicago location prepares for its grand reopening early this year after suffering a fire in October 2018, Chicagoans can visit the Rosemont location to try longtime signature favorites and an array of romantic specials. Valentine’s Day offerings include:


Shrimp de Jonghe – Shrimp sautéed in garlic, butter and Italian breadcrumbs ($24)

Burrata al Forno – Baked burrata over a light tomato sauce, served with crostini ($28)


Ravioli Valentino – Heart-shaped ravioli stuffed with ricotta, fresh cherry tomato and herb sauce ($28)

Risotto – Arborio rice, fresh asparagus and bay scallops ($34)


King Crab Legs – By the pound, served with clarified butter ($69/LB)

Surf & Turf – 8 oz prime filet mignon and succulent grilled shrimp, served with fresh spinach ($75)

Bistecca Fiorentina for Two -- A true Florentine style steak - 40oz. dry-aged and thick-cut T-bone, created in partnership with Northwest Meat Co. ($98)


White Chocolate Mousse ($12)

Le Colonial (57 E. Oak St.)

Le Colonial is celebrating Valentine’s Day with a special three-course dinner of authentic Vietnamese cuisine curated by Executive Chef Quoc Luong. The three-course menu will feature menu items as well as several specialties for each course. The $85 per person menu includes an amuse-bouche, appetizer, entrée, festive dessert selection, and coffee or tea. 

Rebar and Terrace 16 (401 N. Wabash Ave.)

Unending Bubbles at Rebar. On Friday, February 14 and Saturday, February 15, guests can take advantage of a “bottomless” premium Champagne offering. As couples clink glasses, they will also try Rebar’s  Shellfish Tower, featuring an array of fresh seafood options. A dessert for two ends the evening.

Bubbly package options (all include the shellfish tower and dessert) include:

  • $195 per couple – Moët & Chandon
  • $225 per couple - Veuve Clicquot
  • $275 per couple – Dom Perignon

Terrace 16. The restaurant will offer a three- or four-course, prix-fixe menu on Friday, February 14 and Saturday, February 15. Prepared by Terrace 16’s culinary team, guests can choose each course from selection of special items, some of which include:

First Course

Butternut squash soup with pepitas coconut, fresh herbs, pepitas, crème fraiche

Gem salad with strawberry, mascarpone, pistachio, kiwi, crostini

Second Course

Duck confit with risotto, spinach, braised shallots

Wild bluefin tartar with seaweed, caviar, ginger, red oak

Third Course

Wagyu beef 6 oz. filet with pomme puree, onion flower, cauliflower, squash, brandy demi

Smoking sole fish with cabbage dumpling, braised mushroom, poached potato, béarnaise

Organic green circle chicken with  radish, endive, sweet potato terrain, compound butter

Spinach rigatoni with garlic, heirloom tomatoes, cream, zucchini

Fourth Course

Dark chocolate souffle with Grand Marnier creme, anglaise, raspberries

Pistachio and strawberries with pistachio cremeux, strawberry gelée, fresh gold strawberries

Select dishes are also available with vegetarian preparation. Terrace 16’s Valentine’s Day prix fixe offerings are $90 for the three-course tasting ($135 with exclusive wine pairings) or $110 for the four-course menu ($150 with wine pairings). 

Time Out Market Chicago (916 W. Fulton Market)

Celebrate love all week long with activations at Time Out Market Chicago, including:

Trivia @ Tony's (Feb 13): Assemble your smartest friends and put your brains to work at Trivia @ Tony's, hosted at Time Out Market's third-floor rooftop bar. Participants will be treated to six rounds of love-themed questions—just in time for Valentine’s Day—and everyone on the winning team will snag a complimentary ticket to the Laugh Factory in Lakeview, courtesy of Brain Sportz Trivia. Plus, they're sweetening the deal this month by giving the two winning teams Time Out Market cash cards.

Floral Pop-Up Shop with Flowers for Dreams (Feb. 13 and 14): From 11am-7pm both days, Time Out Market Chicago will be hosting a floral market with Flowers for Dreams, located in the Demo Kitchen area on the 2nd floor. Plus, a portion of proceeds will be donated to Lemons of Love to support those fighting cancer.

Raising the Barre: Date night + mixology class (Feb 18): You and your partner will work it out and then stir it up at this 30-minute full-body workout class from Pure Barre, which focuses on low-impact, high-intensity movements. After you’ve worked up a sweat, you and your sweetheart will learn how to build one of Time Out Market’s signature cocktails with the pros behind the bar. Don’t forget to wear comfy workout clothes and pack your yoga mats.

Tzuco (720 N. State St.)

Chef Carlos Gaytan is hosting diners for a Valentine’s Day dinner at Tzuco. Available for one night only, guests can turn up the romance with new choices and guest favorites, including Ceviche Rojo with Ahi tuna, cactus pear aguachile, morita cucumber, pickled red onions, choclos; Pulpo Enamorado with Guajillo oven roasted octopus, carrots, peas, potatoes, tuna aioli, dill; Steak Tartar with Snake Ranch River American Kobe, fried shallots chipotle vinaigrette, quail eggs, chives, bread; Black Truffle Risotto made with black truffle cream sauce, pickled black trumpet, verdolagas Tzuco aged cheese; Costaillas de Res with braised short ribs, parsnip purée, baby kale, orange supreme; and Chicharrón de Pescado with fried red snapper, salsa Veracruzana, pickled vegetables, among many other dishes. 

Virtue (1462 E. 53rd St.)

Notable Chef Erick Williams serves up a four-course menu on Friday, February 14th featuring an array of special items such as Crispy Duck Thighs, herbed dumplings, mustard greens, turnips, Filet Mignon, petite filet, roasted marble potatoes, Visalia puree, Key Lime Torte, key lime mustard, cheesecake, graham and so much more! The Valentine’s Day menu is $74 per person with an option to add wine pairings for an additional $40. 

Woven + Bound (Marriott Marquis Chicago, 2121 S Prairie Ave)

For $60 per person with an option $40 wine pairing, Woven + Bound will offer a special prix-fixe menu for the holiday. This offering is available on February 14 from 5 to 10 p.m. 

First Course

Baby spinach, red wine poached pear, walnuts, whipped goat cheese, champagne vinaigrette

Taittinger Brut, Champagne France

Second Course

Choice of

Lobster carbonara, pancetta, peas, parmesan

Laguna Chardonnay, Russian River Valley


Filet Mignon, Steakhouse potatoes, roasted Brussel sprouts, hollandaise, foie gras bordelaise

Allegrini Valpolicella, Veneto Italy


Dark chocolate passion bombe, passionfruit cream, chocolate shortbread, raspberry coulis

Chocolate Covered Strawberries

Dows White Port, Porto Portugal


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