Romantic Valentine’s Day Plans for the Chicago Foodie

Romantic Valentine’s Day Plans for the Chicago Foodie

In the time when a date usually is meeting for coffee or drinks, a dinner date has become kind of special.

For instance, that time a guy took me out on a first date for drinks, and then halfway through decided to step up his game and buy me dinner, I used it as a cocktail party story because I felt so special. It was simple really, he bought a small pizza for us to share—Papa John’s, but those were just details.

While my taste in men is still developing, I do adore good food.

Windy City Cosmo has rounded up some cute spots to have dinner or brunch. Of course, there are also some other treats if you want to make a romantic Valentine’s date extra special.


King’s Bowl (1500 N. Clybourn) in Lincoln Park’s new plaza, New City, is hosting a special weekend for you and your valentine. The dinner includes a special Valentine’s Day dessert, and, of course, specialty cocktails like the Love Potion #9 and the Stubborn Heart. A DJ will top off your perfectly romantic evening.

Date: Thursday, February 11 – 14, 2016

Reservation: Book Online

Expand Your Palate With Wine Pairings:

Wine is the new water, so why not learn to properly pair it?

Pinstripes: Bistro, Bowling, Bocce in River East is hosting a more traditional romantic evening for Valentine’s Day. The Italian restaurant and upscale entertainment venue is partnering with Milbrant Vineyards for an interactive four-course wine dinner featuring perfectly-paired wines. Guided by a Milbrant expert and Pinstripes Bistro chef, the evening will be both delicious and educational as they demonstrate how each pairing enhances the dining experience.


Reception: Stuffed Dates Gorgonzola, Applewood Smoked Bacon / 2013 Riesling, Evergreen Vineyard, Columbia Valley, Washington

Pasta: Butternut Squash Raviolo Brown Butter & Sage, Honey Spiced Pumpkin Seeds / 2014 Chardonnay, Columbia Valley, Washington

Main: Rain Crow Ranch Bone in Short Rib American Grass-Fed Beef, White Grits, Cajun Shrimp / 2012 Cabernet Sauvignon, Wahluke Slope, Washington

Sweet: Housemade Truffles Assortment of Chef’s Artisanal Hand-Rolled Chocolates / 2012 Red Wine, Brothers’ Blend, Columbia Valley, Washington

Date: Friday, February 12, 2016, at 7:00 pm

Reservation: $45/person

Get Medieval:

Dine with royalty (besides yourself).

Chivalry is not dead at Medieval Times Dinner and Entertainment. Harken back to the romance-filled days of yesteryear and treat your prince or princess to a Valentine’s Day themed dinner & show experience unlike any other at a castle—an actual castle.

The special $110 package includes admission for two, a couples’ photo, a four-course meal, two cheering flags, a light-up sweetheart rose, and two glasses of champagne with which to toast your budding—or established—romance.

Date: Thursday, February 4 – 15, 2016

Reservation: $110 package, Use Code: VDAYWEB16

Get Chocolate Covered:

Katherine Anne Confections (2745 W. Armitage Ave.) in Logan Square is offering a special treat for you and your sweetie.

Make your own truffles, add some champagne and have a fun night out. You’ll create classic hand-rolled truffles with Katherine Anne.

I went to one of her truffle making classes and it was an amazing experience to smell and taste new ingredients. At the end of the night, after measuring, chilling, scooping, and rolling your truffles, you  will leave with a sampling of the truffles everyone created (approximately 10).

Katherine Anne’s Truffle Making Class for Valentine’s Day 2016 Photo: Amanda Elliott

Date: Friday, February 12, 2016, 6:00 p.m.

Reservation: $70/person

Make Dinner Together:

Don’t worry, you don’t have to impress him with your cooking skills. You can cook together. Bake425 is a bake at home, farm to crust pizza concept. They are located right in Evanston and deliver (4:00 pm – 7:45 pm) to your Chicago front door. Bake425 has a variety of veggie topped pizzas as well as meat lover options for your man.

I love that you can make healthy choices while eating pizza. For the sides, add Caesar Salad and even cookie dough to complete your meal. All of the food is pre-packaged and includes clear directions on top of each dish that read more like a letter than directions.

I made the Omnivore pizza with a friend. It was something that got us in the kitchen and turned your standard take-out into a fun little dinner party.

As a Valentine’s Day special, Bake425 is offering a special, custom heart-shaped pizza. All you have to do is choose up to three ingredients and the chef will work on the heart-shaped part.

P.S. it is one of the freshest pizza’s you will ever eat—it even tastes better than some Chicago restaurant pizza. Bake425 sources food from Midwest farms and they focus on organic foods like their artisanal pizza crust and organic tomato puree.  Plus, Bake425 doesn’t use GMOs. It is truly a farm fresh experience that reminded me of this time.

Date: Valentine’s Day weekend or future dates

Reservation: Call 1 (847) 425-1000

Make Reservations for Two:

There is always the simple, more respected option to be picked up with red roses, go to dinner and a movie and stay up all night telling each other how much you love them.

For more traditional Valentine’s Day plans, there’s Valentine’s Day Dinner of Valentine’s Day Brunch.

Valentine’s Day Dinner:

  • Miku Sushi (4514 N. Lincoln Avenue)

Miku Sushi continues to celebrate its 1st anniversary in February by offering half off their Lincoln Square Classic Maki and Traditional Maki rolls, 11 a.m. to 6 p.m. Sunday through Saturday until February 29.

Start off with an Asian-inspired cocktail, such as the Red Octopus with Effen’s vodka, triple sec, Rose’s lime juice, and pomegranate juice (a known aphrodisiac).

Date: Sunday – Saturday until February 29, 2016

Reservation: call 773-654-1277 or book online

  • Osteria La Madia (59 W. Grand Ave.)

Osteria La Madia offers traditional Italian cuisine, featuring housemade pastas, anti pasti, salumi and prosciutto, formaggio, salads, and a full entrée selection. There are more than 75 wines by the glass, as well as bottled wine and craft cocktails.

Date: February 12-14, 2016

Reservation: Three Course: $47, With wine pairings $65, Four Course: $57 (with Pizzetta Selection), With wine pairing $79

Anti Pasti 

Yellow Tail Bruschetta

Foie Gras Ravioli

Spinach and Taleggio Fondue

Chopped Italian Greens, Creamy Herb Dressing, burnt Caramel bacon


Orecchiette, Chicken Sausage, Tomato Conserva, Roast Eggplant, Green Olives

Casoncelli, Butternut Squash Filled Pasta, Brown Butter & Pistachio

Pan Seared Steak Florentine

Wild River Salmon, Fennel, Blood Orange


Chocolate Tortino

Berries with Sweet Mascarpone Cream

Zeppoli, Bitter Chocolate Gelato

Poached Eggs 300 Coal seared beef carpaccio300Pizza 3 300

Valentine’s Day Brunch:

  • Bella Bacinos Chicago (75 E. Wacker Drive)

Bella Bacinos is offering a special Valentine’s Day brunch for you and your valentine. I hear mimosas are in future because brunch comes with a complimentary glass of bubbly. Cheers to you and your love.

Bella Bacinos has more than 600 wines from around the world, with more than 20 wines by the glass.

Specials include:  Make Your Own Omelets ($12),
Very Berry Strawberry Waffle and Chantilli Cream ($8.50), Crème Brulee French Toast ($8.50), Ricotta  Stuffed French Toast ($12), and Heart-Shaped Frittata ($13).

Explore Bella Bacino’s full menu here.

Date: February 13 – 14, 2016, 8:00 am – 2:00 pm

Reservation: Book online 


Amanda Whitfield
Amanda Whitfield

Amanda Whitfield is a writer and speaker and a relationship builder. She believes that meeting people in person is important. After attending numerous fashion, startup, and creative events, she founded Windy City Cosmo is 2015 to help people make connections in the city as they build their businesses, start and end relationships and see and be seen. Over the past three years, the entrepreneurs she’s interviewed have become the most successful in Chicago and Windy City Cosmo won an award in 2017 for her work for female entrepreneurs.

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