February is but a few days away and we’re here to play a little Cupid! Whether you and your better half like to go out and explore new restaurants and dive into unique experiences or you prefer to stay in and enjoy each other’s company, we have rounded up our favorite Valentine’s Day weekend happenings so your plans can go without a hitch!


The Chicago Firehouse Restaurant invites you to celebrate Valentine’s Day on February 14 from 4 p.m. to 10 p.m. at 1401 South Michigan Avenue in the South Loop. Formerly Engine Company 104 of the Chicago Fire Department, The Chicago Firehouse Restaurant infuses the culture of the past to serve the present as an officially designated Chicago Landmark. This Valentine’s Day, guests may indulge in a special menu that brings all the sweet and savory flavors to share with friends and significant others alike. From entrée and starter options like an 8-Ounce Prime Filet Mignon, Potato-Wrapped Halibut and Seared Diver Scallops to ending with a sweet treat of Warm Chocolate Grand Marnier Souffle, Tableside Bananas Foster or Strawberry & Champagne Parfait. The Chicago Firehouse Restaurant delivers a memorable, guest-first dining experience and to book yours, click here.

Love always wins at Carnivale. Celebrate love at Chicago’s most colorful destination with a special menu curated by Executive Chef Carlos Garza available on Friday, February 10 through Sunday, February 12 and Tuesday, February 14. The love bug will also be biting at Carnivale with a Cupid’s Brunch on Sunday, February 12 from 10 am – 2pm. The all-you-can-eat experience will surprise and delight with a variety of Pan-Latin favorites. Tickets to the brunch are $55 for adults and $25 for children ages 10 and under. Soda, coffee and tea included. Reservations to all of Carnivale’s colorful Valentine’s Day specials are available on Tock.

If you are looking to spice up the night and really impress your significant other this Valentine’s Day Komo Chicago, the hot Japanese dining destination on Restaurant Row, has fast become of Chicago’s hottest reservations to snag for date night. Executive Chef Macku Chan showcases a new dimension to his cuisine, combining seasonal ingredients for a modern take on a traditional Japanese meal. This Valentine’s Day, Komo will be offering a decadent 4 course menu featuring Chef’s luxurious creations, creating a romantic experience that won’t soon be forgotten. To make reservations, please click here

Looking for dinner with a view? Take your mate on a date to remember with City Cruises Chicago, who will be offering a selection of unforgettable cruises down the Chicago River and Lake Michigan. Couples looking to impress their dates can choose between Lunch or Dinner Cruises, each complete with live entertainment, a plated dinner with freshly prepared entrees, along with spectacular views of the city. Patrons can opt to upgrade their packages to include a Glass of Champagne or Sparkling Wine, a Single Rose per couple and a guaranteed window seat. Spots are limited and will sell out. Visit here to learn more about the various offerings to choose from this Valentine’s Season.

Thorn Restaurant and Lounge, perfectly nestled within The Rose Hotel in Rosemont has your Valentine’s Day plans figured out for those looking to celebrate a few days early! Whether traveling in and out of O’Hare Airport or looking for a unique destination a quick drive from the city, Executive Chef Nicholas Malloy has crafted a decadent three-course prix-fixed menu to celebrate your better half. The first course offers a rich and fresh burrata caprese, followed by a mouthwatering surf and turf, finished with a decadent raspberry chocolate flourless cake. All couples will also be treated to a champagne toast to celebrate their love. This exclusive dinner will be available Friday, Feb. 10th, and Saturday, Feb 11th, with live music from 7-10 pm on both nights, creating a lovely ambiance for the holiday. Reservations will fill up quickly, please click here to make reservations today.

Enjoy a modern, upscale dining experience in none other than Chicago’s scenic North Shore suburbs when visiting Oaken Bistro + Bar, located in the Forester Hotel. Guests will be thrilled to experience Oaken’s many offerings as the restaurant boasts a delectably bold mix of worldly fare and beverage offerings including signature dishes from savory meats and delicious starters to an adventurous mix of cocktails and spirits to brighten the day, courtesy of Oaken Bistro and Bar’s Executive Chef Christian Alejandro. On February 11 and 14, guests will enjoy a 4-course Valentine’s Dinner for 2 featuring an eclectic mix of specialty menu offerings from Chef Alejandro including Sheep Milk Ricotta, Mussels, Sweet Butter Poached Langoustine, Orange Risotto, and much more.  Guests may additionally enjoy the best of both worlds when booking the Forester Hotel’s Dining Package and enjoy a soothing staycation in addition to a $25 food and beverage credit for use at Oaken Bistro + Bar. For more information or to make reservations visit the Oaken Bistro + Bar website.

Fulton Market Kitchen is making dinner for two an absolute art this Valentine’s Day. Executive Chef Jonathan Harootunian has developed a delicious four course menu to enjoy in the high-style restaurant that doubles as an immersive art experience. For the first course, diners will enjoy their choice of Steak Tartare or East Coast Oysters on the Half Shell served with a Passionfruit Mignonette. Mouthwatering Parisian Dumplings will be on the menu for the second course, or an indulgent Maine Lobster & Wild Mushroom Vol u vent. For the main event, Chef is serving up diner’s choice of a Petite Filet served with a classic Bernaise, artichoke confit and fondant potatoes, or Amish Chicken served alongside grilled asparagus, a wild rice pudding and sherry jus. Art comes to the plate for the fourth and final course, as Chef will be offering lovers their choice of ‘The Bleeding Heart’ Chococake with strawberry truffle or a Dreamsicle Pot de Creme featuring candied citrus. FMK’s special Valentine’s Day menu will be available for $110 per person, and reservations are available via OpenTable.

Love is in the air! To celebrate, Whim Chicago invites lovers to join them on February 11th, 14th, and 18th for Love WHIMS! Couples can immerse themselves into an unforgettable Valentine’s Day Celebration experience in their one-of-a-kind lobby by candlelight, enjoy live entertainment and take a romantic, exclusive trip through the incredible immersive art installation. Tickets are available for purchase at $100 for two people, and will include a bottle of complimentary champagne to celebrate, as well as two craft Valentine’s Day cocktails to sweeten the deal. For more information about the event, visit the official WHIM website here.


Chicago’s favorite pop-up bar, Replay Lincoln Park, is celebrating Gal Pal love with a weeklong celebration Galentine’s Day! Beginning on Wednesday Feb. 8, Replay will host Galentine’s Psycho Bingo at 8 pm; followed by a Galentine’s Parks and Rec Trivia with Baig of Tricks beginning at 7 pm on Thursday, Feb. 9. Those looking for a Ladies Night are invited to check out Replay’s Ladies’ Night on Friday, Feb 10 with DJ Kite mixing up a Queens of Pop playlist throughout with the likes of Lady Gaga, Lizzo, Beyonce, Britney, Taylor Swift, and more. On Monday, Feb. 13 beginning at 6 pm, Replay will host a Galentine’s Day Barre class. Following the class, gal pals can enjoy Happy Hour $2 off drafts and $7 Bubbly Rose, then a Paint and Sip class beginning at 8pm.  As the Grand Finale, Replay will host a Stupid Cupid Valentine’s Day Singles Party on the 14th with $5 High Noon seltzers and $3 Beam Black shots. Details and more tickets can be purchased by clicking here.

Roseland Community Hospital on the Far South Side of Chicago will be launching The Roseland Reserve, which will be a community closet housing non-perishable foods, toiletries, and household items that residents of the greater community can request, as needed, in honor of American Heart Month throughout February. The kickoff event will begin on Valentine’s Day, February 14 and will be an ongoing initiative of giving back to the community. To learn more about how you can make a difference for Roseland Community Hospital Foundation by volunteering or learning more about how they consistently give back to the greater community, please visit here.

For those theatre lovers, Marriott Theatre in Lincolnshire has the perfect date night opportunity. This longest running theater in Chicagoland is kicking off its 2023 season with Big Fish, which tells the story of charming traveling salesman Edward Bloom, who lives life to its fullest, and his relationship with his adult son Will. Patrons will have the option to selection from an array of showtimes throughout the Valentine’s Week, with times varying from 1pm, 7:30pm, 8pm, and 4pm. For more information or to purchase tickets, please click here.

Chicago French Press in the Roosevelt Collection Shops knows how to treat a sweetheart right. Their limited-edition “Sweetheart Bundle” will make for the perfect gift for every coffee lover featuring the brand’s Chocolate Raspberry Truffle, Sugar Cookie and Red Velvet coffee blends.


Valentine’s Day anywhere but at The Rose Hotel in Rosemont just wouldn’t smell as sweet. Those looking for a romantic getaway away from home are invited to book The Rose’s Valentine’s Day Package available throughout the duration of February. The package includes a welcome amenity with sparkling wine and chocolates or macaroons, along with a romantic dinner for two at Thorn Restaurant. Let someone else do the planning for you this year as you enjoy each other’s company. Free parking is also included to rest easy about transportation. For more information or to learn more about booking, please click here.

Treat your better half to a lovely stay at the Canopy by Hilton Chicago Central Loop hotel, the boutique style hotel located in the heart of Chicago’s financial district showering guests with a variety of upscale offerings, amenities, and unique experiences communal spaces, special packages and more, in addition to expertly crafted fare from Executive Chef Tim Lestos of Canopy’s onsite restaurant, Depot 226. Guests may enjoy all that the city has to has offer with Chicago’s most sought after experiences and destinations in perfect reach from the comfort of the hotel from iconic tourist attractions, experiential outings, and more! For more information visit the Canopy by Hilton Chicago Central Loop website.