Raised: An Urban Rooftop Bar
Whether you're treating your Valentine to a long weekend escape, planning a date to remember or a getting a group together to spend the night on the town—there's something to see or do for lovers and friends of all kinds this Valentine's Day in Chicago. Here are eight unique ways to celebrate Valentine's Day in Chicago.



1. Say 'I Love You' with a Stop at Candyality



Chicago's sweet Candyality makes it easier than ever to say "I love you!" with candy. You'll find all your retro favorites at this sugar-filled shop, including giant chocolate hearts, red M&Ms and candy heart charm necklaces. Indulge in Chicago's first licorice bar, which offers a world-class selection of sweet vines, and uncover your candy personality with their Candyscope.

Candyality  |  520 N. Michigan Avenue  *see website for additional locations |   312-527-1212



2. Enjoy a Belle Époque–Inspired Evening of Cabaret

SATURDAY, FEBRUARY 11, at 6:30 and 8:30 p.m.

When love is in the air, what could be more romantic than an intimate musical conversation? Chanteuse Claudia Hommel as she brings her cabaret magic to the Driehaus Museum, transporting you and your lover to Paris for Valentine's Day Cabaret: C'est L'Amour! Tickets include light hors d'oeuvres and drinks. Guests must be 21 years of age.

Driehaus Museum  | 40 E. Erie Street  |  312-482-8933



Driehaus Museum

Or if chamber music revs up your romantic engine, check out the museum's Romantic Duos: An Evening of Classical Chamber Music (Friday, February 17 at 7:30 p.m.), which explores the translation of great conversation into resplendent melody interpreted by the Rembrandt Chamber Musicians.




3. Laugh Your Cares Away with Cupid

FEBRUARY 11, 14, and 18

Stage 773's The Cupid Players

Following successful shows at the 16th Annual Chicago Sketch Comedy Festival, the shamelessly provocative group The Cupid Players of Stage 773 will present Cupid Has a Heart On . . . in Bed! 

Couples, singles and groups of friends can catch the show to be serenaded with hilarious new numbers as well as Cupid classics. With feisty songs about relationships, love and life, guests will be sure to have a "pants-dropping" good time.

The Cupid Players' special 10:30 p.m. late-night performance is offered for those who enjoy a supremely adult-themed show. The one-act performance includes the cast's most loved, risqué (and always sex-positive) numbers.

In addition to the funny, whimsical night of musical comedy, audiences of the February 11 and February 14 shows will be treated to a complimentary champagne toast.

Stage 773  |  1225 W. Belmont Avenue  |  773-327-5252




4. Set Sail on a Valentine's Day Cruise


Odyssey Valentine's Dinner Cruise

Hop aboard the Odyssey, a premier Chicago cruiser, for a Valentine's Day Brunch Cruise. You'll enjoy a buffet-style Brunch Menu as you sail Lake Michigan, with the lovely skyline as a swoon-worthy backdrop. The cruise boards from Navy Pier, reservations are required.

For an evening option, step aboard Chicago's premier lake cruise ship for dinner with an unbeatable view. The Spirit of Chicago is a 192-ft., four-story ship with three dining decks, dance floors, bars and panoramic windows.The two Valentine's Day weekend dinner cruises offer grand buffet-style dining, DJ entertainment, a complimentary champagne toast and a rose for each couple. The cozy and climate controlled decks mean that you won't freeze your socks off. Pricing starts at $100 per person, reservations are required.

Valentine's Day Brunch Cruise
Odyssey  |  600 E. Grand Avenue  |  888-957-2634


Valentine's Day Weekend Dinner Cruises
Spirit of Chicago  | 600 E. Grand Avenue  |  888-957-2634




5. Eat Your Heart Out at Vermilion Restaurant



Vermilion's sultry, red Eat Your Heart Out Prix-Fixe Menu, indulges couples in five luxurious courses featuring oysters, New York strip steak, sinfully rich desserts and more. Each dish is dangerously lush in red, tailored to eat your heart out. $65 per plate. Courses include:

  • Primer Amor: A first course tribute to your first love, featuring Blood Red Indian Street Pani Puri, Flour Shells, Pomegranate Water, and Wine Tapioca Pearls.
  • Heart Beet: Scarlet Salad of Heart of Palm Mousse, Beet, Lobster, Arugula, Cumin, Passionfruit Vinaigrette, and Balsamic Caviar.
  • Shuckling All Night: Aphrodisiac Oysters, Crimson Pomegranate, and Lime Chili Mint.
  • Get You Goan: Goan Red Chimichurri NY Strip Steak or Goan Lamb Shank, served with "Kadai" Sweet Potatoes and Tomato Rice.
  • Sugar, Spice & . . .: Sinfully rich Vermilion Hedonism Chocolate Cake, Ruby Hibiscus Sorbet, and Candied Rose Petals.

Vermilion  |  10 W. Hubbard Street  |  312-527-4060




6. Go Back in Time to a Fateful Valentine's in Chicago History

TUESDAY, FEBRUARY 14, at 5 p.m.

Raised, An Urban Rooftop Bar

Instead of celebrating Valentine's Day with a rather typical, traditional evening, Raised, An Urban Rooftop Bar, invites all to go back in time to the fateful Chicago evening on February 14, 1929, with a St. Valentine's Day Massacre-Themed Chef's Dinner.

The evening will begin with a cocktail reception at 5 p.m., where guests can enjoy specialty cocktails such as The Scofflaw, which originated in 1924 in Paris, France; The Gin Rickey, created in 1903; and a timeless classic, The Side Car, which was invented shortly after World War I. Dinner follows. Tickets are $65 a person.

Raised, An Urban Rooftop Bar  |  1 W. Wacker Drive  | 312-795-3442




7. Enjoy a Romantic Getaway at the Fairmont Chicago


Fairmont Chicago - Hotel - Blog

Indulge in your desires with a romantic getaway in the heart of downtown Chicago at the Fairmont Chicago Millennium Park. Step out for a romantic stroll around Millennium Park, which is just a half a block away, or cap off your vacation with a champagne toast in the intimacy of your luxurious hotel room.

Couples returning to their rooms will also find The Chocolate Bar, a delicious array of homemade decadent treats meant to stimulate your senses, including chocolate-covered strawberries, brownie bits, biscotti or even hot chocolate.

This special Romantic Escape Package includes overnight accommodations at the Fairmont Chicago Millennium Park and The Chocolate Bar for two.

Fairmont Chicago Millenium Park  |  200 N. Columbus Drive  |   312-565-1143




8. Experience a Lava Shell Couples Massage and a Luxe Weekend Away at Waldorf Astoria Chicago


Waldorf Astoria

Sweep your sweetheart off her feet at the Waldorf Astoria Chicago, the luxury getaway located in the heart of Chicago's stylish Gold Coast neighborhood. Throughout February, the elegant Parisian-inspired property will offer a romance-filled package, Love, Luxe & Fire Romance Accommodation, which includes... 

  • Veuve Clicquot and dessert, consisting of heart-shaped sugar cookies or chocolate-covered strawberries, to enjoy with your "sweetie" in one of the 169 guest rooms and suites, which boast a fireplace—perfect for cozying up to in a Windy City winter.

  • One complimentary movie (per evening) to watch in the spacious, residential-style room/suite.

  • 20% off a bespoke spa treatment, including the warming Waldorf Lava Shell Couples Massage, where hot lava shells are positioned on the body to alleviate muscle tension and increase blood circulation. (Rates for a customizable couples massage start at $340 for 60 minutes.)

To further elevate, the True Waldorf Service team is dedicated to creating unforgettable memories with thoughtful, tailor-made add-ons. Personalized touches such as a plush king-size bed covered in rose petals or a candlelit bath with champagne and luxe scented bath salts can be arranged ahead of time and customized according to each guest's "romantic"preferences.

Waldorf Astoria Chicago  |  11 E. Walton Street  |  312-646-1300



What's the most romantic Valentine's Day you've experienced in Chicago? Share with us in the comments. Looking for more Valentine's Day ideas in Chicago? Check out our tips for Valentine's dates at every price.