Love in the City: How to Spend Valentine’s Day in Chicago

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For many, Valentine’s Day is a day to make your significant other feel special. For some, it’s just another day. With Chicago at your disposal, here are some unique ways to spend the holiday, whether you’re treating someone you love or just treating yourself to a night out.

SKYDECK THREE-COURSE DINNER

James Beard Award-winning chef Jonathon Sawyer is serving a romantic evening at Skydeck at the Willis Tower. At Kindling downstairs, guests will enjoy a champagne toast before heading to the 99th floor for a three-course meal. With the view of the city lights, enjoy Heart Puttanesca Pasta with potato gnocchi and Molten Chocolate Cake, a few of the delectable dishes by Chef Sawyer. To end the evening, guests make their way to the 103rd floor for petit fors from West Town Bakery. Reservations can be made on OpenTable.

Potion Cocktail Class at The Cauldron

Discover The Cauldron Chicago and book a magical experience of fantasy inspired cocktails and cocktail making. Book your potion cocktail class today!

CANDLELIGHT CONCERT

Visit the Cafe Brauer for a romantic candlelight concert. The Valentine’s Day show includes an array of love songs, starting with “Romeo and Juliet” by Tchaikovsky and ending with “Kiss from a Rose” by Seal, with Taylor Swift’s “Love Story” included in the middle. The 65 minute show is performed by Metropolis String Quartet and seats are on a first come first serve basis.

BLINDFOLDED MEAL

For a unique date idea that takes the classic dinner date to the next level, try this Dining in the Dark experience. In a dark restaurant lit by candlelight, guests are blindfolded upon arrival and led to their table, where you and your date enjoy a three course meal with vegan, seafood, or red meat options.

THE SECOND CITY

A night on the town is the perfect time to take advantage of one of Chicago’s many theater performances. The Second City is performing “Don’t Quit Your Daydream” on the night of Valentine’s Day with tickets starting as low as $39.

THE SKATING RIBBON AT MAGGIE DALEY

There is nothing more flirtatious and romantic than holding on to your partner for dear life as you attempt to glide around the skating ribbon at Maggie Daley Park. This Valentine’s Day, reserve your spot and rent skates online for $16 or $18 in person, or skate for free by bringing your own skates.

HEART-SHAPED PIZZAS

Pizza is a classic dinner option, and a heart-shaped pizza is the easiest way to win this Valentine’s Day. Several pizzerias around the city offer this special creation that’s sure to win the heart of your lover, including Pizza Portofino, Robert’s Pizza Co., Giordano’s, My Pi Pizza, and Eataly. At Lou Malnati’s, order a heart-shaped pizza and pair it with a giant heart-shaped cookie.

JOIN A WINEMAKING CLASS

The most romantic of alcoholic beverages, this winemaking class will teach you about the drink you’ll be sharing with a loved one over a romantic dinner. This hands-on class at Wild Blossom Meadery teaches how wine is made and includes grape stomping, followed by a wine tasting.

TAKE A COOKING CLASS

At The Chopping Block, elevate a romantic dinner at home with Valentine’s Day cooking classes. Join a hands-on experience with options for Italian, Cajun, or Mexican dishes on February 14 or 15.

AIRE ANCIENT BATHS

Whether you’re looking for a relaxing evening with a loved one or need a night all for yourself, AIRE Ancient Baths provides a variety of experiences filled with massages, thermal baths, and body scrubs. Decked with floral installations and sweet treats, try an exclusive romantic experience with Velvet Love for Two, Love Connection 45′ – Special Edition, Love Connection 60′ – Special Edition, or the signature Wine Bath. Additionally, share the love with an AIRE Gift Box or AIRE E-Gift.

CHICAGO BOTANICAL GARDENS

The Chicago Botanical Gardens is the perfect setting for a romantic outing or a quiet day to yourself. Stop by the week of Valentine’s Day for the Orchid Marketplace, cooking classes and demonstrations, and hands-on baking experiences.

ROOFTOP DINNER AT GODFREY HOTEL

Take Valentine’s Day dinner to the next level with a rooftop bar full of heated igloos. Enjoy the views of the city and stay warm this holiday with a private romantic evening above Chicago. Make a reservation for the rooftop lounge.

LOVE STORIES TOUR

If you love love, and you love Chicago, then the guided tour of “Love Stories of Chicago” is the date for you, or the perfect way to treat yourself. This tour takes you through the city to some of the most romantic places where love stories live in Chicago history. You’ll find some of the most romantic locations in the city and pick up a few date ideas along the way.

ROSEBUD

This Valentine’s Day, spend a night out dining at the luxurious Italian restaurant, enjoying heart-shaped cheese ravioli and other entree options like filet and lobster. To pair with the multi-course meal, guests can choose between two wine bottles. For dessert, Rosebud features Valentino Tronchetto with mixed berries.

TACOMBI 

This downtown taqueria is serving up taco favorites for a sweet and casual Valentine’s meal. Try Tacos al Pastor or Quesadilla Gringas. Pair your dinner entree with a Mexican cocktail, like the Spiked Sandia, which includes tequila, watermelon, and lime. 

ESMÉ ELITE DINING PASS

The Michelin-star restaurant is offering exclusive dining experiences starting at $65 per person. The pass includes three premiere dining experiences, preferential booking, and insider access to the culinary world of Esmé, as well as artist studio visits, gifting discounts, and cooking classes by Chef Jenner.

MACHINE: ENGINEERED DINING & DRINK

Full of exciting Valentine’s Day activities, Machine is offering a range of workshops to fill a week of love. Join their Bouquet Workshop on February 8, or the Galentine’s Day Brunch Cocktail Workshop on February 10. If you just can’t wait to start planning your Valentine’s Day, you can preorder Valentine’s Day Bouquets, made by Machine’s in-house flower shop. Bouquets can be picked up after noon on Valentine’s Day.

CRUSHED HEARTBREAK BAR

Not feeling the lovey-dovey season? Drown your tears in your included shot with a ticket to 90 minutes at The Heartbreak Bar. Along with this interactive welcome shot, you can get your photo taken on Cloud 9, shred some heartbreaking love mementos, cry your heart out with tissues, or indulge in a tarot card reading. For more heartbreak remedies, join The Heartbreak Bar for Sunday brunch.

MARISOL AT THE MCA

For $100, guests can enjoy a Valentine’s Day special 4-course meal at Marisol at the Museum of Contemporary Art. Dinner starts at 5:30 p.m. with a reservation. After dinner, guests can continue the evening watching Wu Tsang’s Moby Dick; or, the Whale at 7:00 p.m., showing in Edlis Neeson Theater.

FARM BAR LAKEVIEW

Outside the bright lights and busy nights of the city, enjoy a casual evening at Farm Bar in the Lakeview neighborhood. On Valentine’s Day and the weekend before, this bar offers romantic dinner specials. Enjoy pita with whipped hummus, Scallops with celery root puree, and a slice of Red Velvet cake. Reservations can be made on OpenTable

ROBERT’S PIZZA & DOUGH CO.

Enjoy this Valentine’s Day special: dinner for two and a Heart-Shaped Ice Cream Pizza at Robert’s Pizza & Dough Co. On Saturday, February 10 and Wednesday, February 14 this pizzeria is offering special 4-course meals. The Valentine’s Menu includes choice of prosecco or two specialty cocktails, two small plates, salad, pizza, and a dessert, including the Heart-Shaped Ice Cream Pizza. Reservations can be made on the website.

TAREAUX TAVERN

Bring some Parisian flair to your Valentine’s Day at Taureaux Tavern. With a special Valentine’s Day menu that includes a 32 oz porterhouse bordelaise for two or a 4pc Oyster Special. Top off the night by trying Taureaux’s alcoholic specials such as L’amour a Paris (Love in Paris) for $16. Make your reservation on Tock.

MOE’S CANTINA

It’s date night in the River North. Celebrate Valentine’s Day with a complimentary Mezcal tasting and heart-shaped churros at Moe’s Cantina on Thursday, February 15 from 6-8 p.m. Moe’s also serves $10 cocktail specials such as Get Lucky and Amor Prohibido, the perfect pairing for a $4 taco deal.

TREE HOUSE CHICAGO

Celebrate Galantine’s Day on Thursday, February 15 at Moe’s Cantina. Try a $10 Cherry Limeade Pucker-Up cocktail, share a Neapolitan Heart Shaped Pizza, and enjoy Happy Hour deals like ½ off bottles of wine, $10 Sleigh Sips, $5 Mango Cart and ½ off wings. Bring your girls to the Tree House for a spunky night out.

THE CAULDRON CHICAGO

Take a night out to The Cauldron for Valentine’s Day or Galentine’s Day. This magic bar is sharing its first Valentine’s Day with its guests by offering new love potions at the walk-in bar. “The Love Bomb” and “The Ice Breaker” are two featured cocktails you need to try. Upon entering, guests will be greeted with a heart-shaped balloon and glass of bubbly. The highlight experience is “The Cupid’s Cauldron” interactive potion brewing class. Tickets start at $64.99. 

GEJA’S CAFE

Recognized by OpenTable as one of the top 100 Romantic Restaurants in the nation, Geja’s Cafe is the perfect place for an early or late Valentine’s date. This restaurant is so popular that reservations for Valentine’s Day sold out within a minute of offering. However, when you book a reservation any date February 5 through February 24, you can still enjoy a romantic evening out or buy a gift card to share the love.

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