Valentine’s Day Specials and Romantic Events in Chicago
Valentine’s Day in Chicago arrives with extra momentum this year, stretching across a whole weekend and inspiring restaurants, hotels, rooftops, and spas to go all in on romance. From candlelit steakhouse dinners and ingredient-driven tasting menus to skyline views, dance floors, and indulgent overnight packages, the city offers countless ways to celebrate love from February 11 through February 15. Whether you are planning a classic dinner date, a high-energy night out, or a full weekend escape, these Valentine’s Day specials in Chicago set the scene for something memorable.
Rooftop Romance and Nightlife Experiences
Dinner and Dancing at ROOF on theWit
High above the city, ROOF on theWit turns Valentine’s weekend into a whole sensory experience. On February 13 and 14, couples are invited to enjoy a three-course dinner paired with Champagne, skyline views, and DJ-led dancing 27 stories above downtown. The evening blends romance with energy, complete with thoughtful touches like floral gifts and sweeping city vistas that make the night feel elevated in every sense.
Pilates Pink Party at ROOF
For couples or friends who prefer a wellness-forward celebration, ROOF’s Valentine’s programming also includes a themed Pilates event on February 14. The DJ-driven workout pairs movement with music and finishes with a festive brunch bite, creating a playful alternative to the traditional dinner date while still leaning into the spirit of the holiday.
Classic Steakhouse and Elevated Dining Destinations
The Barn Steakhouse, Evanston
A longtime favorite for romantic occasions, The Barn Steakhouse embraces Valentine’s Day with seasonal additions alongside its regular menu. Expect refined steakhouse classics, dramatic shared entrées designed for two, and decadent desserts that linger long after the last course. The intimate Evanston setting and timeless approach make it ideal for couples who appreciate tradition done well.
Gene & Georgetti
Few places feel as inherently romantic as Gene & Georgetti, and Valentine’s Day only heightens its old-school charm. Across the long weekend, diners can explore notable additions to the menu alongside signature steaks, housemade pastas, and classic cocktails. The experience is rooted in nostalgia, comfort, and indulgence, perfect for couples seeking a timeless Chicago date night.
Ingredient-Driven and Contemporary Valentine’s Menus
Eden
At Eden, Valentine’s Day takes on a more modern, seasonal tone. The kitchen leans into thoughtful sourcing and balanced flavors, offering refined dishes that highlight winter ingredients without feeling heavy. A carefully crafted dessert program rounds out the experience, making Eden a strong choice for couples drawn to creativity and restraint rather than excess.
FireLake Grill House & Cocktail Bar
Located inside the Radisson Blu Aqua Hotel, FireLake Grill House & Cocktail Bar presents a multi-course Valentine’s menu built for sharing. Guests move through elegant starters, comforting soups or salads, and polished main courses before ending with a choice of decadent desserts. A complimentary bottle of Champagne adds a celebratory note to the evening.
LeTour Social Kitchen & Bar, Evanston
Throughout Valentine’s week, LeTour Social Kitchen & Bar offers a cozy, candlelit atmosphere paired with special dishes designed for sharing. From rich starters to indulgent entrées and playful desserts meant for two, the menu encourages lingering and conversation, making it a relaxed yet romantic option just outside the city.
Romantic Hotel Packages and Staycation Ideas
Hotel EMC2 and The Albert
Couples looking to turn Valentine’s Day into a complete getaway can book the Be Mine Package at Hotel EMC2, which pairs a stylish overnight stay with dinner at The Albert, wine, and a late checkout. The Albert also offers a standalone three-course Valentine’s menu inspired by Italian flavors, blending comfort and elegance in a setting that feels intimate and warm.
theWit Chicago: Dining, Spa, and Overnight Escapes
At theWit Chicago, Valentine’s Day unfolds across dining, wellness, and overnight experiences. Couples can enjoy special three-course dinners at State and Lake Chicago Tavern, unwind with a Valentine-themed spa treatment infused with strawberry and Champagne notes, or book winter packages designed around theater nights or extended stays. Together, these offerings create a layered celebration that moves seamlessly from dinner to relaxation to rest.
Why Chicago Shines on Valentine’s Day
With its mix of iconic dining rooms, creative new menus, skyline rooftops, and thoughtfully designed hotel experiences, Valentine’s Day in Chicago offers something for every type of couple. Whether your ideal celebration involves dancing above the city, lingering over a steakhouse classic, or escaping into a cozy staycation, these Valentine’s Day specials make it easy to turn February into a celebration of connection, indulgence, and time well spent together.
