Valentine’s Day in Hyde Park

Valentine’s Day is Wednesday, February 14, and it’s time to get rolling on all your romantic plans. Hyde Park area businesses are offering hotel packages, special dining menus, shopping events, and more. If you learn of any other local options, please message us to add to this list. Happy Valentine’s Day!


Ascione Bistro

1500 E. 55th Street

Ascione Bistro is celebrating Valentine’s Day from Friday, February 19 through Wednesday, February 14 – offering a prix fixe dinner for two priced at $139. Couples may choose one appetizer (arancini, meatballs, or fried calamari), one entree per person (filet mignon Oscar Style, squid ink linguine with lobster and scallops in a spicy Cognac sauce, lobster ravioli, or chicken parmigiana with pasta marinara) and one dessert for the table (tiramisu, limoncello mascarpone cake, or cioccolato cake). Your favorites from the regular menu are available as well. The restaurant is taking reservations and pickup pre-orders at 773-363-8161.


Ascione Bisto’s special Valentine’s Day menu.



1201 E. 60th Streeet

Join us in the dining room and prepare to enjoy a romantic, four-course experience with your special someone for $75 per person. Guests will receive a complimentary glass of rosé bubbles, in addition to a house-made selection of mignardises to take home at the end of the evening. Menu selections include items like Hamachi Crudo, Scallops, Valbreso Tagine, and more! This special menu will be available during lunch or dinner service, beginning on Wednesday, February 14 through Friday, February 16. Click HERE to reserve.

BarDavid is offering a special four-course menu for Valentine’s Day.


Bob’s Pizza

1518 E. Harper Court

“Bob’s has a FREE Valentine’s Day sweet treat just for you!⁠ All dine-in, carryout & delivery orders on Wednesday, February 14 will receive one FREE special Valentine’s Day-themed oatmeal cream pie with their order.”


Bob’s Pizza special offer.


Busted Bra Shop

1013 1/2 E. 53rd Street

Hyde Park’s Busted Bra Shop carries bras in band sizes from 28-56 in A-P cups as well as lingerie in sizes XXS-10XL. Their expert staff is trained in measuring you for the perfect fit. Gift cards also available.


Busted Bra shop has a full selection of lingerie, bras, panties, and more.


Cajun Boil and Shake

5500 S. Shore Drive

The restaurant is offering a special menu for two people from February 9-18 with a starter, entree, and dessert for $110 total. Starter options include Six-Piece Hush Puppies or Brussel Sprouts, entree options include 1.5 lb Snowcrab and 1.5 lb Shrimp or two Lobster Tails and 1.5 lb Shrimp, with beignets for dessert. Click HERE for reservations.




Cajun Boil and Shake is offering a special menu for two people.



1509 E. 53rd Street

Celebrate Valentine’s Day at Chant with all-day drink specials and live music from 5-8 p.m. with Blended Soul. No cover charge, and reservations are not required, but there’s limited capacity so arrive early.


Valentine’s Day at Chant.


Connect Gallery

1451 E. 53rd Street

Connect Gallery is partnering with Reformed School to present the “Shop in the Name of Love Market” on Saturday, February 10 and Sunday, February 11 from 11 a.m – 7 p.m.


Connect Gallery is hosting a pop-up Valentine’s Day shop.



Cornell Florist

1645 E. 55th Street

Cornell Florist is encouraging customers to pre-order for Valentine’s Day. Shop their selection online HERE or call to order at 773-324-1651.


Cornell Florist is offering floral arrangements at a variety of prices for pickup and delivery.



5226 S. Harper Avenue

Nothing says “I love you like the gift of chocolate-covered strawberries, truffles, chocolate-dipped Oreos, decorated caramel apples, and more. Use promo code VERYSWEET for 10% off pre-orders placed before February 10. Click HERE to order sweets for your sweetie.


Stop by Kilwins in Hyde Park for sweets for everyone on your list.


Mesler / SOPHY Hotel

1411 E. 53rd Street

Hyde Park’s SOPHY Hotel is offering several staycation options, including the “SO – In Love” package, with a two-night stay in one of their spacious guest rooms, one bottle of Champagne, one box of Vosges chocholate, one $100 credit to Mesler for brunch, and gift certificate for outdoor skating for two at Midway Plaisance Park with rentals.


SOPHY’s guest rooms.


The Promontory

5311 S. Lake Park Avenue West

The Promontory is hosting Bernard Crump’s Mecca Monday’s presents “Pre-Valentine’s Day Love Jam” with Dr. Sax James Perkins and BJ on Monday, February 12, from 7-10 p.m. Doors open at 6 p.m. Learn more and get tickets HERE.


“Pre-Valentine’s Day Love Jam at The Promontory.”


The Quadrangle Club

1155 E. 57th Street

This century-old restaurant on the University of Chicago campus in Hyde Park will offer a romantic dinner and live violinist duo (sisters Teja and Tierra Syers) this Valentine’s Day. Guests will dine on a specialty Valentine’s Day prix fixe dinner & cocktail menu. Following the meal, a decadent sweets table will be available for all guests. Ticket price per person is $75 Member / $95 Non-Member. Reserve your table today.


Violinist duo Teja and Tierra Syers at The Quadrangle Club.


The Silver Room

1506 E. 53rd Street

The Silver Room has lots of great gift options for your Valentine, as well as some much-needed self-love and wellness items too! Don’t miss the “Lovestruck” photobooth pop-up event on Sunday, February 11 from 12-5 p.m. – $45 for three photos. “@ddesigns_ is back for another Photo Booth pop-up in front of a hand-painted backdrop by @treylegit! Curated for you and the loves of your life, come in your freshest V-Day-inspired look.” Also – Thursday, February 15 from 6-8 p.m. don’t miss the SPECIAL LOVE EDITION of Grown Folks Stories. This month has a theme – LOVE STORIES! The good, the bad, the unbelievable. We want to hear them all! @grownfolksstories happens every 3rd Thursday of the month at @promontorychicago!


“Lovestruck” photo-booth pop-up event at The Silver Room.


“Love Stories” version of Grown Folks Stories on Thursday, February 15.


Sneakerville 88

5241 S. Harper Avenue

If your honey’s love language is a new pair of sneakers, you’ve got to stop into Sneakerville 88, owned by father and daughter James and Jayme Denman.



Stan’s Donuts & Coffee

5225 S. Harper Court

Love (and sugar) is in the air! Whether you’re celebrating Galentines Day on February 13th with your friends, Valentine’s Day on February 14th with your honey, or just soaking up the rosy atmosphere, Stan’s Donuts & Coffee has the goods to help you enjoy the season.

This month we’re offering several specials, including lovely boxes of a dozen mini donuts, limited edition turtle cake donuts, and specialty heart-shaped donuts topped with decorative, Valentine sprinkles. Stan’s Donuts is offering this special to customers until February 14th. Pre-orders begin on February 7th, but boxes will be offered in-store from the 10th to the 14th. Click HERE to order.


Stan’s heart-shaped box of mini donuts available for order.


Strugglebeard Bakery

5221 S. Harper Court

Quinton McNair at Strugglebeard Bakery in Harper Court is hosting a “Love & Libations Valentine’s Day Bake & Sip” event on February 10 from 5-8 p.m. Admission includes hands-on baking class, Champagne welcome, games, and complimentary cocktails. Click HERE for tickets. The bakery is also offering the “You Make It Better” Valentine’s Day gift box with red velvet cookies, red velvet macarons, chocolate dipped cookies, chocolate dipped pretzels, and a decorative box and card. Click HERE to order now.


Strugglebeard’s Bake & Sip Event.
Strugglebeard’s gift box.


Suuri Design

5225 S. Harper Court

Suuri Design, the mother/daughter-owned jewelry boutique located at 5225 S. Harper Court, is featuring candles with customizable labels for you and your sweetie in addition to their great selection of unique jewelry.

Stop in today for a customized candle.


Suuri’s heart pendants.


Truth Be Told

1227 E. 60th Street

Truth Be Told is serving a $75 four-course menu with a $30 optional wine pairing from 4-10 p.m. on February 14 and February 16-17. Menu options include oysters Rockefeller, fried calamari, butter lettuce salad, surf and turf, and raspberry and lemon sorbetto with fresh berries. Click HERE for reservations.


Truth Be Told’s four-course menu.



1462 E. 53rd Street

Chef/owner Erick Williams’ restaurant is consistently recognized as one of the most romantic dining spots in the city, and this year they are celebrating Valentine’s Day on Tuesday, February 13, and Wednesday, February 14. Make your reservations HERE.