Chicago Valentines Day 2020 Ideas

What to do for Valentines Day? Here is a short list of some of our picks.

Valentine’s Day Things To Do

Tuco & Blondie

Tuco & Blondie Valentine’s Cookie Decorating

Gather the little ones for a sweet treat just in time for Valentine’s Day – cookie decorating! We’ll supply the cookies, frosting and decorations on February 9. Kids can DIY their own paper Valentine’s for their loved ones! Tickets are just $10 per seat.

Date: Sunday, February 9, 2020, 10am-3pm
Price: $10 per person

Art Institute of Chicago

Naked at the Art Museum Scavenger Hunt

Adventure awaits on team-building scavenger hunts that reveal the AIC’s secrets. As you follow clues to answer tricky, entertaining questions, you’ll get a whirlwind tour of the museum’s masterpieces—and possibly also solve a murder or show off some wizarding skills. Discover the most fun you’re allowed to have in an art museum.

Date: Saturday, February 15, 2020
Price: $38 per person

King of Cups Chicago

King Of Cups “King Of Hearts” Valentine’s Day Package

Celebrate Valentine’s Day at the King Of Cups! Each package includes two craft cocktails, champagne split, chocolate covered strawberries, and a rose (one per couple).

Date: Friday, February 14, 2020 – Sunday, February 16, 2020
Price: $12-$30

aliveOne Chicago

“alOveOne” Valentine’s Day Party

aliveOne, the Lincoln Park neighborhood bar that combines the very best of music and spirits, will host an “alOveOne” themed evening on Valentine’s Day. Specials will include $3 Bell’s Two Hearted drafts and $8 “alOveOne” cocktails with Ketel One, LaCroix Pamplemousse, lime juice and demerara. aliveOne will be decked out in Valentine’s Day decor and offer candy hearts and cupcakes from Sweet Mandy B’s. Guests can start the night with a half-off everything happy hour from 5 p.m. to 7 p.m. followed by an emo dance party in the back room with music like Fall Out Boy, Taking Back Sunday, Blink 182 and Dashboard Confessional. DJ sets from DJ Faithful Anchor start at 10 p.m.

Date: Friday, February 14, 2020
Price: Free live music, $4 to $8 drink specials

Easy Bar Chicago

DIY Valentine’s Day Cards and 80’s Party at Easy Bar

Chicagoans are invited to Easy Bar in Wicker Park to create Valentine’s Day cards for their sweetie all week leading up to the holiday. Easy Bar will provide the supplies (free of charge; supplies are limited), and while crafting, guests can sip on daily specials like $6 glasses of wine on Monday, $2 and $3 select beers on Tuesday, $6 signature cocktails on Wednesday and more. Easy Bar also offers a half-price everything happy hour Monday through Friday from 5 p.m. to 7 p.m.

On Friday, February 14, Easy Bar will host an 80’s Valentine’s Night Bash at 10 p.m. featuring the best tunes from the 80’s. Specials available all evening will include $8 Barcelona Mules made with PAU Maui vodka, ginger beer and Meiomi wine float.

Date: Monday, February 10, 2020 through Friday, February 14, 2020
Price: $8 drink special

Estelle's Chicago Inside

4th Annual “Wine About Your Love Life” at Estelle’s

On Valentine’s Day, Estelle’s invites Chicagoans to their 4th Annual “Wine About Your Love Life” night featuring half-price glasses of wine, available all evening for $6 each (normally $12). Wine selections include Beckstoffer ’75 Company Cabernet Sauvignon, Planet Oregon Pinot Noir, Angels & Cowboys Rose, Iconic Sidekick Chardonnay and Babich Sauvignon Blanc. Other specials will include a $5 “Be My Tindertine” shot. Candy hearts will be available for customers if they want to give a “sweet” special message to their Estelle’s crush.

Date: Friday, February 14
Price: $6 glasses of wine

The Rambler Chicago

Valentine’s Day The Bachelor Themed Trivia at The Rambler

Guests are invited to get their group dates together to play The Bachelor themed team trivia at The Rambler in North Center on Friday, February 14 at 7:30 p.m. Prizes will include a 10 person The Bachelor season finale viewing party for first place and a five person viewing party for second place. The viewing parties will include appetizers and drinks.

Themed drink specials will include Cran I Steal Him for a Second with Koval Cranberry, Mionetto Prosecco, club soda and orange ($9), the Wild Windmill Spritz with Fragola Wild Strawberry Liqueur, Mionetto Prosecco, club soda and strawberry ($9), a Fantasy Suite Martini with Mozart White Chocolate Strawberry Cream, Wheatley Vodka, White Creme de Cacao, cream, strawberry ($11) and more. Additional specials will include $4 Truly with a custom flavor station, $5 Tequila Rose and $7 Bollicini Sparkling Cuvée. To reserve a table, email

Date: Friday, February 14, 2020 at 7:30 p.m.
Price: No cover; $4 to $9 themed cocktails

Remedy Chicago

Love-Themed Coloring Night and Heart-Shaped Pizzas at Remedy

Chicagoans who visit Remedy on Valentine’s Day can show off their artistic talents or doodle while they drink and participate in a Valentine’s Day coloring night. Remedy will provide “love” themed coloring books and coloring supplies along with candy and heart-shaped pizza (while supplies last). Specials will include $1 off all wine by the glass (normally $10 to $12). Wine selections include Sidekick Chardonnay, Babich Sauvignon Blanc, Angels and Cowboys Rosé, Ruffino Prosecco, Planet Oregon Pinot Noir, and 75 Wine Co Cabernet.

Date: Friday, February 14, 2020
Price: $1 off glasses of wine

The Owl Chicago

Glitter Beer at The Owl for Valentine’s Day

Located a few blocks from the heart of Logan Square, The Owl will host a casual Valentine’s Day on Friday, February 14 with a half-price happy hour from 6 p.m. to 8 p.m. (excluding shots), and $6 glasses of BBLZ sparkling wine will be available all night. To celebrate the holiday, Illuminated Brew Works has added pink glitter to their Brony Double Dry Hopped Double IPA which will be available exclusively at The Owl. Candy and Valentine’s Day cards will also be available for guests to write special notes on and give to the sweetie they spot in the bar. For guests looking for a late-night Valentine’s Day party, DJ Fess Grandiose will be spinning from 10 p.m. to close.

Date: Friday, February 14, 2020

Taking your loved one to a Burlesque show is always fun as well! Check out our guide to Chicago Burlesque Show’s.

Valentine’s Day Restaurants

Le Sud Chicago

Le Sud Valentine’s Day Prix Fixe

Valentine’s Day prix fixe by Chef Michael Woodhall. The meal includes Hama Hama oysters on the half shell, roasted beet Napoleon, 60-day dry-aged grilled NY strip, trout almondine, flourless chestnut cake and creme brulee for $65 per person. Optional wine pairings may be added for $20 per person (Rosé, Bordeaux and Sauternes selections). The prix fixe specials will also be offered a la carte. Le Sud will be open from 5-11 p.m. on Valentine’s Day.

Date: Friday, February 14, 2020 – Sunday, February 16, 2020
Price: $65 per person | ala carte pricing available

Lockwood Chicago Inside

Valentine’s Love Story Dinner at Lockwood Restaurant & Bar

The Twin Violas are professional musicians, graduating from the University of Music in Bulgaria playing electric violins and acoustic violas. Let sounds from the Twin Violas flame your beau’s delight over three courses of prix fixe treasure this Valentine,s Day. Features will include quince and charred octopus salad, roasted beet with couscous and pomegranate seed, lamb trio, Chilean Sea Bass and manjari chocolate mousse. Each course may be ordered individually with separate a la carte pricing.

Date: Friday, February 14, 2020 – Sunday, February 16, 2020
Price: $60 per person | ala carte pricing available

Hubbard Inn

Valentine’s Day Prix Fixe Dinner at Hubbard Inn

Diners can enjoy a romantic Valentine’s Day dinner at the newly renovated Hubbard Inn with a three-course prix fixe menu for $50 per person created by Executive Chef Eric Babula. A beer and wine pairing menu will be available for an additional $25 per person.

Highlights include a dozen East and West Coast Oysters, Heart-Shaped Ravioli (Semolina dough, braised beef short rib, house ricotta, poached beef jus, parmesan reggiano), Sweet Potato Gnudi (handmade pillows of sweet potato and ricotta, brown butter, crisp sage, balsamic reduction), Chocolate Porter Brownie (valrhona chocolate, vanilla porter reduction, applewood smoke, bourbon caramel, fruit powder, vanilla bean ice cream, pickled raspberry, basil), Rosé Panna Cotta (vanilla bean curd, rosé granita, rosehip syrup, sparkling rosé) and more. The complete menu is available upon request. For reservations, visit

Date: Friday, February 14, 2020
Price: $50 per person; $25 beverage pairing

Mastro's Chicago Bar

Valentine’s Day Dessert Special at Mastro’s Steakhouse

Guests can enjoy dinner with their sweetie and indulge in a month-long Valentine’s Day dessert special at Mastro’s. The $18 decadent dessert features a chocolate devils food butter cake baked with a cocoa and cream cheese topping served with chocolate ice cream, and drizzled with raspberry sauce and white chocolate ganache.

Guests can also treat themselves to Mastro’s cutting edge menu of prime steaks and fresh seafood including New Zealand King Salmon Filet, Big Eye Tuna sashimi-style, Alaskan King Crab Legs, Japanese A5 Wagyu, Broadleaf Wagyu Tomahawk Chop and more.

Date: Available Saturday, February 1, 2020 through Saturday, February 29, 2020
Price: $18 specialty dessert

Morton's Chicago Wacker

Valentine’s Day Steak and Lobster Feature at Morton’s

In celebration of Valentine’s Day, Morton’s in Chicago, Naperville, Northbrook, Rosemont and Schaumburg will feature an indulgent Steak and Lobster Special for $59. The entree includes an 8-ounce filet mignon paired with a 1¼ pound lobster topped with lobster butter sauce and finished with grated parmesan cheese and a savory puffed pastry.

Date: Thursday, February 13, 2020 through Sunday, February 16, 2020
Price: $59 steak & lobster specials

Onward Chicago

Valentine’s Day Chef Specials at Onward

Diners can enjoy a romantic Valentine’s Day dinner at Onward in Rogers Park with chef specials created by Executive Chef Patrick Russ. Features will include Alaskan King Crab Bisque (mirepoix, gochujang, creme fraiche; $14), 16-ounce Bone-In Braised Short Rib (white bean purée, sassafras, roasted baby carrots; $42), Island Creek Oysters (champagne granita, blood orange caviar; $2.50 each), and Berkshire Pork Loin (ricotta gnocchi, parsnip puree, char siu, rapini; $32). All guests will receive a complimentary pour of champagne to toast. For dinner reservations, call 872.888.8776 or visit

Date: Friday, February 14, 2020
Price: $2.50 to $42 specials

Tuscany Chicago

Valentine’s Day Dinner at Tuscany

Tuscany on Taylor Street will offer a la carte specials in celebration of Valentine’s Day on Friday, February 14 and Saturday, February 15. Created by Executive Chef Victorio Padilla, highlights include Grigliata Mista (shrimp, calamari, cannellini beans, garlic herb sauce; $15), Agnolotti (shrimp filled, citrus cream sauce, crab meat; $20), and Aragosta e Filetto (butter baked 6-ounce lobster, grilled 5-ounce filet, sauteed spinach; $42). The complete menu is available upon request. Reservations are recommended.

Date: Friday, February 14, 2020 and Saturday, February 15, 2020
Price: $8 to $42 menu specials

Uvae Chicago

Valentine’s Day Chef Specials and Wine Pairing Menu at Uvae

Guests will indulge in decadent chef specials and wine pairings this Valentine’s Day weekend at Uvae in Andersonville. Created by Chef Charity Smith, specials range from $9 to $26 and will include a Pear & Prosciutto Carpaccio (paired with Paul Roger Champagne 3-ounce, $15; 6-ounce, $20; 9-ounce, $25), Warm Butter Poached Lobster Salad with tarragon citrus vinaigrette (paired with Domaine Jean -Paul Paquet Saint Veran White Burgundy 3-ounce, $14; 6-ounce, $18; 9-ounce, $22), Smoked Beet Dip (paired with Domaine Turner Pageot 48H Rosé 3-ounce, $12; 6-ounce, $15; 9-ounce, $18), Beef Tenderloin with a rosé vinaigrette, pink peppercorns, pickled watermelon radish (paired with Domaines Lupier el Terrio Garnacha 3-ounce, $18; 6-ounce, $22; 9-ounce, $26), and Lemon Herb Sole with baby roasted carrots (paired with Honig Reserve Sauvignon Blanc 3-ounce, $14; 6-ounce, $17; 9-ounce, $20).

For dessert, diners can indulge in a $9 Sparkling Sorbet Float. Chef Smith’s signature French Macarons will be provided as a special complimentary treat at the end of the meal. Reservations are recommended by booking with Resy.

Date: Thursday, February 13, 2020 through Saturday, February 15, 2020
Price: $9 to $26 specials

Yugen Chicago

Valentine’s Day 8-Course Tasting Menu at Yugen

In celebration of Valentine’s Day, Michelin-starred Yūgen in the West Loop will offer an 8-course tasting menu available for $250 per person (additional $150 for beverage pairing) from Thursday, February 13 through Saturday, February 15.

Created by Executive Chef Mari Katsumura, the tasting menu features seasonal canapés like Japanese Souffle Pancake (shiso cured trout, creme fraiche, Osetra caviar), Beef Jerky (fermented shiitake, cippolini onion, garlic aioli) and Alaskan King Crab (Motoyaki, Kaluga caviar, crispy potato). Other highlights include King Trumpet Soup (cherry boshi, housemade tofu, breakfast radish dashi), Sashimi (Fuyu persimmon, fresh yuzu, Royale caviar) and more. Supplements for an additional price include A5 Miyazaki Wagyu (shishito, eggplant, mitsuba bearnaise; $45) and a White Truffle for the Lobster Rice, freshly sliced for $75. The complete menu is available upon request. For reservations, call 312.265.1008 or visit OpenTable.

Price: Thursday, February 13 through Saturday, February 15
Date: $250 per person; $150 beverage pairing

Portillo's Heart Shaped Cake

Portillo’s Heart Shaped Cake

Heart shaped chocolate cakes are available for pre-order here starting Tuesday, January 14th for $15.99. You can pick this sweet treat up at any Portillo’s location from February 7th-16th. You could also have it delivered to you or a special someone by pre-ordering online. Hurry! Pre-order while supplies last! You can also place a heart-shaped cake order by calling 688-YUM-BEEF.

Lou Malnati's Heart Shaped Photo

Lou Malnati’s Heart Shaped Pizza

Heart shaped pizzas will be available in all Lou Malnati’s pizzerias starting Friday, February 7th through Valentine’s Day weekend, Sunday, February 16th.

Cupid’s best tip: Save some time by grabbing a frozen heart shaped pizza from our freezer case before Valentine’s Day, or order your pizza half-baked and finish it in your oven at home!


Chicago born and raised. Always looking for new places.

TC has 335 posts and counting. See all posts by TC

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