It’s time to crack out the heart shaped cookie cutters and pull out every romantic comedy in your movie collection because one of the most highly anticipated Hallmark holidays is almost here! If you are looking to spend Valentine’s Day with the same romantic plans or posted up on the couch eating every last chocolate in the heart shaped box your mom bought you, it is time to switch it up! From workout classes featuring Bachelorette alums to rooftop events with champagne and chocolate fondue, we have rounded out the best events and activities to celebrate Valentine’s Day in the Windy City!


For the traditional Chicago romantic

Geja’s Café, 340 W. Armitage, is planning the most romantic Valentine’s celebration in its 53-year history. Beginning Sunday, February 11th through Saturday, February 17th, the renowned “Restaurant of Romance” will be elegantly decorated for the holiday and feature rosé sparkling wines and champagnes, live flamenco and classical guitarists, photo keepsakes, and delicious sizzling hot fondue cuisine. The Valentine’s festival will also feature its first ever Valentine’s Day “Lunch of Romance” experience and the ever popular Celebration of Marriage Night, where couples receive an added discount based on the years they have been married.  For more information or to book a reservation, call (773) 281-9101 or visit


Enjoy a night of champagne, chocolate fondue, and rooftop views

Raised Bar, 1 W. Wacker Drive, is bringing love to all in the Chicago Loop with a special Valentine’s Day: No Date Required event on Wednesday, February 14, 2018 from 4pm to 12am. The year-round rooftop hangout, which boasts panoramic views of the Chicago River and city skyline, invites couples and friends alike to make a toast to their special love with the exclusive Champagne Cocktail Menu. To pair with the cocktail menu, dessert options for two offered include a sharable Chocolate Strawberry Fondue Box with large strawberries, white chocolate, dark chocolate, milk chocolate, cocoa nibs, and crunch pearls; and a Raspberry Lychee Coconut Terrine, with rose crystal sugar, champagne gelee’, and a pink macaroon. Nicholas Barron, a Chicago-based sultry Blues singer and songwriter, will be providing live music from 6 to 9pm. This is a non-ticketed event. For more information, please visit or call 312-795-3444.


Burn off your Valentine’s Day chocolate box and meet a member from the Bachelorette!

Orangetheory® Fitness, hailed by The New York Times as “the best one-hour workout in the country,” is hosting a special Galentine’s Day event on Tuesday, February 13, along with exclusive Valentine’s Day sessions on Wednesday, February 14 at select Chicagoland studios. The Galentine’s Day event will be held at the South Loop and Hyde Park studios, and will feature a selection of spa services and a special guest appearance from Diggy Moreland of The Bachelorette and Bachelor in Paradise in the South Loop studio. The Oak Park and Frankfort Studios will also offer Valentine’s Day sessions for all couples on Wednesday, February 14.


Let the professionals handle your dinner plans this year

The Albert, a contemporary restaurant located at 228 East Ontario St, is taking care of the cooking and the romance this Valentine’s Day by offering an exclusive Valentine’s Day Four Course Prix-Fixe menu, topped with a half bottle of sparkling, for $90 per person. Full table participation only.  For more information or to book a reservation, please call (312) 471-3883.


Experience an evening of decadent dining and cocktails to pair

Staytion Market & Bar, 1 W Wacker Drive, will be hosting a special three-course menu for those looking to make their romantic evening a full dining experience. This special a la carte Valentine’s Day menu includes: 1/2 Dozen Oysters, with yuzu soy foam and caviar; Bitter Green Salad, with goat cheese cream, candied beets, almond powder, burnt citrus, and hibiscus vinaigrette; Bone in New York Steak, with arugula chimichurri, crispy potato, baby artichokes, and grilled asparagus; Housemade Gnocchi, with roasted chicken, peas, tomatoes, pancetta, garlic, pine nuts, and garlic marsala cream, and a tasting from the petit four and chocolate cart for dessert. Staytion will also be offering a cocktail pairing for each course. Local Chicago artist Rebecca Brunner will be providing live music from 5pm to 8pm. To discover more, visit or call 312-372-7200.


Add a little humor to your romance-filled plans

Celebrate your Valentine’s Day with a performance from one of Chicago’s oldest sketch comedy groups, The Cupid Players. In honor of the romantic holiday, The Cupid Players will be hosting The Cupid Players V-Day Special on Saturday, February 10th at Stage 773, 1225 W Belmont, with shows at 8PM and 10:30PM. Those booking the 8PM show will be treated to a complimentary champagne toast and goodie bag. For more information or to book tickets, please visit


Escape your busy schedule with a romantic staycation

Bring the romance back into your relationship and treat your significant other to the ultimate staycation getaway at Fairmont Chicago, Millennium Park, 200 N. Columbus Dr. is . For Valentine’s Day, guests can take the guesswork out of planning a romantic evening with Fairmont Chicago’s Romantic Escape Package, through February 28, 2018. Starting at $237, the Romantic Escape package includes overnight accommodations for two in a luxurious Fairmont guestroom, one bottle of Veuve Cliquot champagne, six gourmet dipped strawberries delivered to the room, and rose petals scattered on the bed upon arrival.


Dinner and a show AND an overnight night stay? Yes, please!

Looking to switch up your normal Valentine’s Day plans in the Windy City? Take your loved one for a night on the town complete with tickets to a Broadway in Chicago production, dinner for two, and an overnight stay!  Cambria Chicago Loop – Theatre District, 32 W Randolph St , honors its close connection to Chicago theatre with exclusive Broadway In Chicago packages. Guests will enjoy a special night downtown including an overnight stay, dinner for two, and tickets to experience one Broadway In Chicago’s most popular productions of all time with the Hamilton package.  Also available is the Broadway Package, which is perfect for those looking to spice up their theatre evening in the Windy City. Both packages are now available for guests to book. For more information or to book this package, please visit


Treat your significant other to a dining experience outside the city

Love is in the air as Valentine’s Day is near. In light of the most romantic evening of the year, Pete Miller’s Steak and Seafood in Evanston and Naperville are opening their doors to guests with a couples-inspired menu for the special February holiday. The two stunning restaurants are offering a pre-fixed Valentine’s Day menu Friday, February 9 through Wednesday, February 14 for $85 per couple. The shared style menu will offer unique appetizers, entrees, sides and desserts including firecracker shrimp or Shanghai calamari for two, pan-seared salmon with lemon beurre blanc and edamame succotash, short rib ravioli with maitake mushrooms, artichokes, carrots, ginger puree, merlot reduction and sage butter, roasted Yukon gold potatoes, crème brulee and more. For more information, please visit


Brunch your way through this Hallmark holiday

All hearts are aligned when bottomless mimosas and Bloody Marys are involved. Nevin’s Brewing Company, 12337 South Rt. 59, is hosting a Valentine’s Beer & Brunch on Sunday, February 11th. This events includes a la carte menu options such as Double-Crossed Beer Batter Chicken & Waffles, Duck Confit Hash and Eggs, and Midnight Pigs and a Blanket. In addition to this, guests can take part in a Midnight Pig Build – Your – Own Bloody Mary Bar and sip on a variety of specialty craft cocktails. For more information or to book your reservation, please call 815.436.3900.


Get your girl squad together for a night of theater

With Valentine’s Day near and “Galentine’s” Day plans quickly solidifying, First Folio Theatre (Mayslake Peabody Estate at 31st St. & Rt. 83) presents the perfect “Ladies Night Out” production for the season with the Chicago Premiere of WOMEN IN JEOPARDY, by Wendy MacLeod. WOMEN IN JEOPARDY, a biting comedy that explores the lives of best friends and divorcées Mary, Jo and Liz who are always looking out for each other, even when they start to suspect that one’s new boyfriend is a serial killer, opens Saturday, January 27 at 8 p.m. and runs through Sunday, February 25, 2018. To purchase tickets, visit


Who said singles can’t celebrate Valentine’s Day, too?!

Muldoon’s Irish Pub, 133 W Front Street in Wheaton, is hosting a Singles Awareness Anti-Valentine’s Party on Saturday, February 10th from 9PM to 1AM. Attendees can sip on delicious specialty cocktails such as Love Potion #133 made with Jameson Irish Whiskey, Apple Puckers, splash of cranberry and a caramel rimmed glass and dance the night away with music mixes by DJ Tony Trixx. For more information, please call 630.668.8866.


For those who waited a little too long to pick up a Valentine’s Day card

Two hours left before dinner and you STILL do not have your Valentine’s Day card for your sweetheart? Looking to be a little more adventurous with your DIY skills this year? Paper Source, a Chicago-based premier paperie and gift retailer, has you covered! With fun and trendy gift items and cards, Paper Source is the one-stop-shop for all your Valentine’s
day  needs! Head to one of their 125 stores in the U.S. or visit their website at which offers nation-wide shipping, to pick out all your heart-themed goodies.