The ultimate guide to Valentine’s Day in Chicago

As Valentine's Day 2024 approaches, we’ve curated a list of top-tier dining destinations, luxurious accommodations, and captivating attractions spread across the Windy City. From cozy bistros with candlelit ambience to romantic and relaxing escapes, our guide is designed to make Valentine’s Day an unforgettable event for couples and loved ones.

Skydeck Chicago’s Pie in The Sky Experience

Book a dinner for two in the sky during the month of February at the Pie in The Sky experience at Skydeck. The three-course meal features a heart-shaped Giordano’s deep dish pizza, salad, dessert, and a breathtaking view of the city.

• Date: Thurs., Feb. 1 - Thurs., Feb. 29
• Time: 7 p.m. on Friday and Saturday or 10 p.m. on Thursday and Friday
• Location: 233 S Wacker Dr, Chicago,
• Price: $150 per person
• Website: TheSkydeck.com

Valentine’s Day at AIRE Ancient Baths

AIRE Ancient Baths offers a serene experience for Valentine's Day, whether for couples, friends, or solo relaxation. Special berry-toned floral installations by a local florist will be on display for a limited time, and various exclusive rituals — including massages and unique bath experiences — are available. Gift options for those wanting to treat loved ones are available to deliver digitally or via shipped gift boxes.

Featured experiences include:

• Love Myself: A 45-minute massage using basalt stones and a choice of oils, complemented by a thermal tour and fresh fruit juice
• Ultimate Blossom Ritual: A renewal experience for couples inspired by flowers, including a 30-minute exfoliation and a floral body mask on warm marble beds
• The Signature Wine Experience: Immerse in the antioxidant properties of Spanish Ribera del Duero red grapes in an exclusive Wine Bath, along with access to the Ancient Baths, a cranial massage, and a grapeseed oil massage

Entry gives access to six different baths, including hot and cold temperatures, a steam bath, a salt bath, and a bath of a thousand jets.

• Date: Varies
• Time: Varies
• Location: 800 W. Superior St., Chicago, IL
• Price: Varies
• Website: Beaire.com

City Cruises Chicago Premier Valentine's Day Dinner Cruise

Cruise on Lake Michigan with City Cruises Chicago for a romantic Valentine's Day evening or Galentine’s Day celebration. Enjoy stunning city views, a three-course meal, cocktails, and DJ music, all in a breathtaking setting.

• Date: Sat. Feb. 10, Sun., Feb. 11, Wed., Feb. 14, and Sun., Feb. 17
• Time: Varies
• Location: Lake Michigan
• Price: $77+
• Website: CityCruises.com

Teatro ZinZanni's "Love, Chaos, and Dinner"

Celebrate Valentine's Day with a spectacular mix of cirque, comedy, and cabaret at Teatro ZinZanni. Housed in the historic Cambria Hotel's Spiegeltent, the event promises top-tier talent and a gourmet multicourse feast, accompanied by Chicago's finest live musicians.

• Date: Wed., Feb. 14 - Sun., Feb. 18
• Time: Varies
• Location: 32 W. Randolph St., 14th Fl.
• Price: $99+
• Website: ZinZanni.com

Trump Chicago's Luxurious Valentine's Day

Toast to the month of romance at Terrace 16 with a luxurious four-course prix-fixe meal, complemented by stunning views of the city skyline from the 16th floor of Trump International Hotel & Tower Chicago. Celebrate the evening with a complimentary glass of champagne and live entertainment.

• Date: Sat., Feb. 10
• Time: 5 p.m. to 11 p.m.
• Location: 401 N. Wabash Ave
• Price: 4-course Prix-Fixe Dinner - $145 per person, Vegetarian 4-course Prix-Fixe Dinner - $95 per person
• Website: TrumpHotels.com

Valentine's Day at Rosebud

Celebrate Valentine's Day at Rosebud, a renowned Italian restaurant, with a special $175 dinner for couples. The menu features heart-shaped cheese ravioli and coconut shrimp appetizers, a selection of filet & lobster, seabass, or crabcake entrees, two bottles of wine, and the Valentino Tronchetto dessert with mixed berries.

• Date: Wed., Feb. 14th
• Time: Varies
• Location: Multiple locations
• Price: $175 per couple
• Website: RosebudRestaurants.com

Valentine’s Day Weekend at Acanto Restaurant + Wine Bar

Across from Millennium Park, Acanto is celebrating Valentine’s Day with a special four-course prix fixe menu, offering dishes like lobster spaghetti, garlic-crusted rack of lamb, frambozen panna cotta and an option for expertly paired wines. This is the perfect spot for an intimate atmosphere with authentic Italian cuisine.

• Date: Wed., Feb. 14 through Sun., Feb. 18
• Time: Varies
• Location: 18 S. Michigan Ave.
• Price: 4-course prix fixe menu for $125
• Website: AcantoChicago.com

Valentine's Day at Color Factory

Immerse yourself in color during an evening at Color Factory and take a stroll through the Colors in Bloom spring activation. For this special night, only ages 21+ will be allowed. 

• Date: Wed., Feb. 14
• Time: 5-8 p.m.
• Location: 320 W. Jackson Blvd.
• Price: $33-$39
• Website: Colorfactory.co

"Sweet on Rush Street" at Chicago Marriott Downtown Magnificent Mile

Book a romantic overnight staycation at Chicago Marriott Downtown Magnificent Mile to experience its exclusive Valentine's Day couples package, including a special sweet treat upon arrival, a champagne toast that evening at Reviver Bar, and breakfast for two in Harvest Restaurant. Use code LVU or ROM when booking online.

• Date: Fri., Feb. 9 - Sat., Feb. 17
• Time: Varies
• Location: 540 N. Michigan Ave.
• Price: $250+
• Website: Marriott.com

Valentine's Day at Carnivale

Carnivale is hosting a Valentine's Day celebration with a special menu on February 14th and an all-day, all-you-can-eat Cupid’s Brunch on February 11th. Enjoy a blend of Latin-inspired dishes and brunch classics in a vibrant setting.

• Date: Sun., Feb. 11 and Wed., Feb. 14
• Time: 11 a.m. - 6 p.m. (Sun.) and 5-9 p.m. (Wed.)
• Location: 702 W. Fulton Market
• Price: $55/adults, $25/kids (Sun.) and $149 per couple (Wed.)
• Website: CarnivaleChicago.com

Valentine’s Day at FONDA Cantina

At FONDA Cantina, Chef Miguel Escobar is offering a vibrant menu featuring traditional Mexican cuisine, with dishes like mole risotto and trout pibil. These dishes are available as a three-course prix-fixe with the regular a la carte menu also available for guests.

• Date: Wed., Feb. 14th
• Time: Varies
• Location: 1735 Benson Avenue, Evanston
• Price: $49 per person
• Website: EatAtFonda.com

Valentine's Day Dinner at Proxi

Indulge in a lavish three-course dinner this Valentine’s Day at Proxi, located in Chicago's West Loop. Chef Andrew Zimmerman offers a menu with eclectic choices like Fanny Bay Oysters, Thai-style Beef Tartare, Lamb Kofta Kabob, and Dark Chocolate Marquis, elevating the evening with culinary finesse.

• Date: Wed., Feb. 14th
• Time: Varies
• Location: 565 W. Randolph St.
• Price: $95 per person
• Website: ProxiChicago.com

Valentine’s Day at Mercadito

Enjoy Mercadito’s Valentine’s Day tasting for two, featuring a variety of choices, from guacamole to tacos. The offerings include special add-ons like the “LOVE-ster taco” with butter-poached lobster and the “La Vida Rosa” cocktail.

• Date: Wed., Feb. 14
• Time: Varies
• Location: 108 W. Kinzie
• Price: $50 per person
• Website: MercaditoRiverNorth.com

Valentine's Day at Michael Jordan's Steakhouse

Celebrate love this Valentine's Day in the upscale ambiance of Michael Jordan’s Steakhouse on the Magnificent Mile. Enjoy a luxurious pre-fixe menu featuring Lobster Bisque, Beet Salad, Petite Filets with Lobster Butter, and a Chocolate Extravagance dessert. Opt for Booth 23 for an intimate dining experience, and consider staying at the InterContinental Chicago Magnificent Mile for a complete romantic evening.

• Date: Wed., Feb. 14
• Time: Varies
• Location: 505 N. Michigan Ave.
• Price: $195 per person
• Website: MichaelJordansSteakhouse.com

A month of Valentine’s Day at Alma Hotel Zachary

Alma’s ‘Love, Alma globes’ return, offering a unique way to celebrate loved ones while enjoying panoramic views of Wrigley Field and Gallagher Way. Indulge in sparkling rose, macaroons and chocolate-covered strawberries, or savor shareables like bacon-wrapped dates and surf and turf, while enjoying vinyl love songs, games and Polaroids to capture memories. 

• Date: Thurs., Feb. 1 through Thurs., Feb. 29
• Time: Varies
• Location: 3630 North Clark Street
• Price: $35 per person on weekdays, $50 on weekends
• Website: AlmaHotelZachary.com

​​"Palentine's Day" at Whirlyball

Bring along six pals for an exciting outing at Whirlyball, and receive a free classic pizza, large gutter balls, or pretzel bites when you book a whirlyball court, bowling lane, or laser tag arena. Promotion must be mentioned during advanced bookings.

• Date: Mon., Feb. 12 - Sun., Feb. 18 
• Time: Varies
• Location: 1825 W. Webster Ave.
• Price: $81+
• Website: Whirlyball.com

Valentine's Day Dinner at The Chicago Firehouse Restaurant

Savor a sumptuous 3-course Valentine’s Day dinner at The Chicago Firehouse Restaurant in South Loop. Guests can choose from an array of exquisite dishes including Prime Filet Mignon, Pan-Roasted Alaskan Halibut, and decadent desserts like Warm Chocolate Cake and Key Lime Pie. Additionally, a special Valentine’s Day event will occur in the Blue Room with a performance by Elaine Dame and a special menu.

• Date: Wed., Feb. 14th
• Time: 4-9:45 p.m. (regular dining room), 6:30 p.m. (Blue Room)
• Location: 1401 S. Michigan Ave
• Price: $95 per person (regular dining room), $25 (Blue Room)
• Website: ChicagoFirehouse.com

Valentine’s Day at Geja's Cafe

Geja’s Cafe will transform into a romantic destination for its annual Valentine’s Day celebration, complete with festive decor, making it one of the city’s most romantic spots. The celebration features three special dinner times, where diners can enjoy a premier three-course meal of cheese, entree and chocolate fondue, complemented by a glass of Pommeroy Rose.

• Date: Wed., Feb. 14
• Time: 4 p.m., 6:30 p.m., or 9:00 p.m.
• Location: 340 W. Armitage Ave.
• Price: $125 per person
• Website: GejasCafe.com

Valentine's Day Tasting Menu at Esmé

Celebrate Valentine's Day at Esmé with a unique tasting menu by Chef Tomaska and his partner, Katrina Bravo. Immerse yourself in a romantic and whimsical Michelin-starred experience inspired by Raspy Rivera's artwork, with the option to add luxury supplements.

• Date: Sat., Feb. 10 - Sun., Feb. 11, and Wed., Feb. 14
• Time: Varies
• Location: 2200 N. Clark St.
• Price: $310 per person
• Website: EsmeChicago.com

Valentine's Day Wine Dinner at Hyatt Lodge Oak Brook

For those in the suburbs, indulge in a 4-course Valentine’s Day Wine Dinner at the Piazza restaurant pop-up at Hyatt Lodge Oak Brook. The evening features a cocktail reception, a wine-paired gourmet meal by Executive Chef Leonard, and live-string music, creating a perfect romantic ambiance.

• Date: Sat., Feb. 10
• Time: 6 p.m.
• Location: 2815 Jorie Blvd.
• Price: $120 per person
• Website: Hyatt.com