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Where to Spend an Evening of Romance for Valentine’s Day 2023

Sfera Sicilian Street Food

Sfera Sicilian Street Food (5759 N Broadway, Chicago, IL 60660) offers Sicilian cuisine with a Chicago twist in Edgewater. The LGBT-owned eatery uses Sicily’s recipes, techniques, and food culture. Sfera is open daily from 10am-6pm. For Valentine’s Day they have created a dinner for spending a night in. 

Valentine’s Day Dinner for Two – 2023 Available for pick up or delivery. Order via Tock. The special meal includes:

  • Your choice of a pair of specialty Arancini 

  • Your choice of one signature Salad

  • Burrata with Pomegranate, Balsamico and Pistachios over mixed Greens

  • Your choice of a Heart-Shaped Sfincione Pizza 

  • Two Cannolis – Raspberry-Lemon cannoli & Pistachio cannoli 

  • Saffron Sour Cocktail Base to make a signature cocktail or mocktail at home

  • $62 per package (serves 2), prepaid

The Goddess and Grocer

Celebrate Valentine’s Day with sweet treats and gift baskets from The Goddess and Grocer – pick up available at multiple locations & delivery is available as well. 

  • Chocolate Covered Strawberries 6 for $18

  • Decorated Cake Pops 8 for $24

  • Valentine’s Day Cupcakes 6 for $30 

  • Hand Decorated Shortbread Cookies 4 for $16

  • Macrons 6 for $16

  • Valentine’s Day 6” Cakes 12 for $30 

  • Cookie Gift Boxes $25 each 

Pre-assembled gift baskets: 

  • DATE NIGHT IN – Canard Duchêne Brut Champagne, Katherine Anne Chocolate Truffles, assorted French Macarons, Chicago Salumi Charcuterie, Marin French Brie, Rustic Bakery flatbread + two Goddess Hand Decorated Valentine’s Day Shortbread Cookies $100
  • GALENTINE’S DAY – Spend a night with your best gal and enjoy two Prosecco splits, two ESW Beauty Face Masks, Torres Truffle Chips and a pair of French Macarons + Chocolate Covered Strawberries $50
  • SEX + CANDY – Som Picked Wine, Big Orgasm Adaptogens Chocolate Bar + Vinoos Champagne Wine Gummies. $45
  • INNER GODDESS – Featuring a handmade Mosser Glass Lady Soap Dish, Self Goddess Crystal Bath Bomb, Self-Care 101 Sweeter Cards Chocolate Bar, Self Goddess Aura Mist, best selling Anecdote Candle, two ESW Beauty Face Masks, Honey Belle Exfoliating Loofah Soap + two Kin Euphorics Sparkling Beverages $125

Photo courtesy of Kristen Mendiola for Sfera Sicilian Street Food

Yardbird Chicago 

Yardbird will be serving a three course prix fixe meal for $95 per person. 

  • Appetizers (Choice one)
    • Maine Lobster Bisque: sherry, tarragon crisp, fresh herbs
    • Kale Mango Salad: pickled mango, roasted sweet potato, avocado, dried cherry, goat cheese crumble, toasted sunflower seeds
  • Entrees (Choice one)
    • Beetroot Potato Gnocchi: braised leeks, shaved pecorino, roasted walnuts, pea tendrils, crispy sage brown butter
    • Skillet Seared Scallops: Butternut squash, fennel slaw, roasted apple and fennel reduction, haricot verts
    • 14oz Ribeye: smoked celery root, asparagus, trumpet mushrooms, horseradish bearnaise
    • Lobster Tail and Truffles are available for add on with an additional fee. 
  • Dessert (Choice one)
    • Chocolate Éclair cake: Yellow cake, dark chocolate ganache, vanilla cream eclairs
    • Banana Pudding Cheesecake: Chocolate cookie crust, whipped cream, chocolate sauce

Good Ambler

The West Loop café and bakery from Chef Kevin McCormick has a variety of chocolates, custom cakes, and seasonal individual cakes available at the shop or via pre-order on Tock here. 

  • Bonbons: Available in various sized sets with fruity, nutty, boozy, and spiced flavors.
  • Chocolate Teddy Bears
  • Chocolate Covered Strawberries
  • Raspberry Chocolate Petit Gateau: Devils food cake with raspberry & red wine compote, raspberry mousse, chocolate-anise crunch and rich chocolate cream.
  • Chocolate Torte: Flourless chocolate cake, milk chocolate cremeaux, dark chocolate mousse, chocolate Glacage.
  • Chocolate Bars

The Robey

Valentine’s day menu is going to feature a 4 course meal for $70 available February 11th and 12th as a supplemental menu and on the 14th at the only menu available!

  • Course one: Ahi Tuna- soy vinaigrette, Avocado, Sesame, Chili
  • Course two: Carrot Cavatelli- harissa glaze, sumac, sunflower granola
  • Course Three: Choice of: 
    • Roasted Top Sirloin- roasted broccoli, potato, horseradish 
    • Seared Scallop- sweet pepper coconut stew, roasted cauliflower, crispy calamari
  • Course four: Dark Chocolate – cashew, cranberry, banana
  • Final bite- Chocolate covered strawberry marshmallows 

Love, Robey Hotel Package

  • Stay Dates: Feb 10-19
  • Booking Dates: Jan 16-Feb 18
  • Must be booked at a minimum of 1 day prior to arrival
  • Inclusions: Bottle of bubbly, charcuterie board for 2, & 5 chocolate covered strawberries.
  • Pricing: Best Available rate + $50 for 2 people


  • Schedule a private pasta making class with executive chef Don Walker at Formento’s. Chef Walker will lead guests through the cooking process of Gnocchi while enjoying a selection of passed appetizers and beverages. This exclusive class costs $2,500 for a group of 10 to 15 people and is held at Nonna’s or one of three premier private dining spaces.
  • Valentine’s Day Special
    • Crab Cake- preserved lemon, choron
    • Fettuccine- alfredo, maine lobster, tarragon gremolata
    • Roasted Whole Snapper- salsa verde
    • Heirloom Carrot- calabrian chili, pesto, pine nut
    • White Chocolate Cheesecake- red fruit cremeux 
  • Drink feature: “Fragoli”- Corazon tequila (or vodka substitution), strawberry, lime, luxardo cherry 

Canal Street Eatery

This special menu for February 14th includes:

  • Soup: Porcini Mushroom Bisque (GF)
  • Burrata: Cherry Mostarda, Candied Pistachio, Frisee, Balsamic Vinegar, Grilled Sourdough
  • NY Strip & Lobster Tail: Bearnaise Prep, Warm butter
  • Red velvet Sheet Cake: Strawberry cream cheese frosting, spiced pecans, strawberry hot fudge

You can secure your spot for this deal at $45 per person

Spending Valentine’s Day at home this year? Yardbird has guests covered with their classic dinner menu available for pick-up and delivery. Place orders here.


Pearls and Bubbles: LeTour’s take on Caviar and Champagne. 

  • 4 Caviar options:
    • Hackleback and Bubbles: $80
    • Crown Osetra and Bubbles: $150
    • The Perfect Trio, all of the above: $225

All of LeTour’s 30g caviar selections are of the finest quality and simply served with creme frâiche and toast points. All are sustainably raised, harvested and domestic.

  • A Tower of Love, for two of course! $95
    • Oysters on the half shell
    • Hand harvested raw diver scallop

Goodambler Sandynoto 093

Photo courtesy of Sandy Noto for Good Ambler


On Tuesday, February 14th, guests can celebrate Valentine’s Day by transporting themselves to the mountains of Peru with Tanta’s 4-course menu experience. For $65/person, guests can select Peruvian options such as their Tiradito Lujurioso (White Fish Sea Urchin), Smoked Salmon, and more. 


1st Course

  • TIRADITO LUJURIOSO White Fish Sea Urchin, Chalaquita, Oyster Sauce

2nd Course

  • CAZUELA ACEVICHADA DE ALMEJAS Y CONCHAS Clams, Mussels, Hot Cebiche Sauce, Lima Beans Powder, Crostini

3rd Course (CHOOSE 1)

  • SMOKED SALMON Maitake Anticuchero, Chaufa, Smoky Rocoto – Peppers Sauce


  • CHANCHITO GLASEADO Pork Tenderloin Marinated in Peruvian Spices, Butternut Squash & Carrots Puree, Rocoto – Hoisin Glazed, Crispy Quinoa Granola, Shaved Asparagus & Baby Carrots

4th Course

  • ROSE Peruvian Chocolate Semifreddo, Rose & Perries, Dried Rose Petals


On Friday, February 10th and Saturday, February 11th, guests at Frontier have the option to order a Tomahawk Steak and dessert for two for $125. Those seeking to pair their steak with something red or bubbly can also add on a bottle of Jordan Cabernet ($123) or a bottle of Nicholas Feuillete (sparkling rosé or brut for $99). 

Frontier Valentines Day 2023

Flyer courtesy of Frontier

The Godfrey Hotel

The Godfrey offers a, “Bubbles + Dessert,” package which can be requested upon booking. From the initial entrance to the room, guests will be greeted with two Moët & Chandon mini splits and two jars of confectionary cake flavors, Red Velvet and Devil’s Chocolate.

The hotel also includes additional romantic amenities like the outdoor Winter Wonderland at I|O Godfrey which offers rooftop views of the southern Chicago skyline. Couples can also use outdoor heaters, fire pits, s’mores-making kits, a seasonal menu of shareable plates, and bubbling hot cocktails including the Naughty Hot Chocolate made with Godiva Chocolate Liqueur and cinnamon, and The Godfrey Toddy hot-infused and served tableside with Woodford Reserve.

Crudo 1 Pc Amy Ulivieri

Photo courtesy of Amy Ulivieri for The Godfrey Hotel

Stan’s Donuts & Coffee

Stan’s Donuts & Coffee Heart Shaped Gift Boxes are filled with romantic donut flavors. Each heart is filled with 12 mini donuts – 6 Devil’s Food Cake and 6 Chocolate Dipped– and available for pre-order and pickup from February 10 through 14. 


At the Michelin-starred Middle Eastern restaurant, diners can choose a four-course choose your own adventure menu. Diner’s can also choose to enhance their experience by adding on a wine pairing. 


This Valentine’s Day, experience a tasting menu experience from Chef Tomaska and his wife/partner, Katrina Bravo. At Esmé, diners can select a tasting menu inspired by the artwork of Amanda Love. 

Bar Esmé

Diners can select a four-course menu for $150.00 per person. On the menu, diners will receive an Amuse of Osteria Caviar, Mushroom, and Chicken Skin. For the second course, diner’s can choose a Duck Ravioli then have their choice between Monk Fish a la Normandie or Wagyu Au Poivere.

El Che Steakhouse & Bar 

El Che pays homage to Argentina’s asados with a wine list that is 100% sourced from South America. Crafted by General Manager and Beverage Director Alex Cuper, El Che offers a look into the variety of wines available on the southern continent.

Michael Jordan’s Steak House 

At Michael Jordan’s Steak House, diners can select a variety of steaks and seafood, including flights of beef cuts and dishes adorned with lobster tails. On Valentine’s Day the restaurant is offering a special menu for two ($180) featuring their garlic bread with blue cheese fondue, choice of lobster bisque or little gem salad, a porterhouse with twin 6 oz lobster tails and lobster mashed potatoes complete with “Chocolate Heaven” to finish. 


This Valentine’s Day, a special multi-course dinner from Chef Andrew Zimmerman. To start, diners will be presented a series of amusements such as Char Siu Foie Gras Dumpling, Golden Kaluga Caviar Pommes Souffle, and more. To follow, diner’s will be presented a four-course menu that include classics such as the Roasted Crab Chawanmushi, Sourdough Cavatelli, Hay Grilled Beef Striploin, and more. When making a reservation, guests can also pre-select wine pairings ($59pp) or pre-order Champagne (both by the glass and by the bottle) that will be poured immediately on guests’ arrival.


A four-course Chef’s Menu featuring dishes such as Tater Tot Chaat, Coal Roasted Scallops, Grilled Lamb Satay, Foie Gras Steamed Bun, and more. 

The Press Room 

The Press Room is inviting Chef Jordan Dominguez into its kitchen to prepare a 15 course Omakase Experience for $150 per person with an optional $60 per person beverage pairing, including two glasses of wine, one specialty cocktail, and one sake. There will be two seating times at 5:30PM and 7:30PM for an hour and a half each. 30 people can reserve spots for each seating. Tickets are available on Tock.


Gioia in West Loop is offering a set, three-course menu for $110 per person featuring a selection from its regular menu and specials for each course. The antipasto special is Aragosta, featuring lobster terrine, smoked cauliflower, Oscetra caviar, watercress and cured organic egg. For the pasta or secondo course, the specials include Tagliolini featuring squid ink tagliolini, crustacean and seafood medley with tomato Datterini sauce and artichokes, as well as Tonno Tonnato, a seared ahi tuna with creamy tonnato sauce and roasted baby winter vegetables. And the dolci special – Tonito al Cioccolato, a chocolate soufflé with pink grapefruit, Campari granita and Moscato mousse. There will be three available seating times at 4:30, 6:30, and 8:30 PM, lasting for two hours each. Reservations can be made on Resy. 

Stans Valentines Minis Lifestyle 2022 2

Photo courtesy of Stan’s Donuts & Coffee

Truluck’s Rosemont

In addition to their regular men, the following specials this Valentine’s Day:

Offered Friday, February 10th – Tuesday, February 14th

  • King Crab Ravioli made with fresh-made pasta, corn bisque, asparagus, parmesan. ($48)

Offered all February

  • Chocolate Strawberry Cake – Fudgy chocolate cake with strawberry cream cheese icing and topped with a chocolate-covered strawberry ($14)
  • TRU Love Cocktail (The Voila!) – A sensory tour de force of dry ice smoke, vodka, cava, Chambord, pineapple juice, raspberries ($16)

Reservations can be made via Open Table or by calling. 

Img 3556 Edit Crop

Photo courtesy of Truluck’s


Celebrate Valentine’s Day with a dining experience at Indienne in River North. Chef Sujan Sarkar will be preparing a special 5-course tasting menu (with surprises) for $175 per person. The menu will be available for non-vegetarians and vegetarians. There will also be a +$70 per person optional wine pairing available. Reservations will open via Tock on Monday, January 16.

Indienne Dining Room 6

Photo courtesy of Neil John Burger for Indienne

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