Too Haute to Trot: Chicago’s Most Extravagant Valentine’s Day Plans

Want to go the extra mile for Valentine’s Day? Give the gf or bf the royal (or saintly) treatment? These once in a lifetime packages, weekends, and specials will make your sweetie swoon. And we mean completely over the top, in the unforgettable sort of way.

Once in a Lifetime Night at the Trump

Designed to assist men or women in executing an elaborate surprise proposal, this unique overnight celebration starts from $250,000/night and includes one night accommodation in a Grand Deluxe Lake View suite, coordinated proposal from the 89th floor penthouse, a diamond engagement ring from the Ivanka Trump Jewelry Collection at Marshall Pierce & Company, air transportation to/from Chicago, as desired, transportation in a Rolls Royce limousine to/from hotel, diamond cuff links from Marshall Pierce & Company, La Perla lingerie, In-suite private dinner for two prepared by Executive Chef Frank Brunacci, welcome bottle of Dom Perignon Champagne, two dozen, long-stemmed red roses, full morning of couples treatments at The Spa at Trump, in-room American breakfast for two, and complimentary late check-out.

Trump International Hotel & Tower Chicago. 312.588.8000.

All You Need is Love

Gentlemen, the Elysian did the work for you—all you need is love to complete this ultimate Valentine’s Day package. A car and driver will pick you up (anywhere in the Chicagoland area) and whisk you away for a night in a Premier Gold Coast Suite, where, upon arrival a beautiful bouquet awaits. Cozy up to the fireplace with your sweetheart, then, head to RIA, two-star Michelin restaurant, for a romantic, four-course dinner for two. During dinner, surprise your beloved with a gift of either an afternoon of beauty at the Elysian Spa or a shopping excursion with our renowned fashion stylist. Before settling in for the evening, enjoy an after-dinner toast in Bernard’s, the intimate hotel bar. Wake to breakfast in bed or in Balsan and head to the spa for relaxing Elysian massages, the perfect ending to the perfect getaway.

Become a Two Star Michelin Chef for the Day

On February 13th Chef McLeod will teach gentlemen how to cook a three-course meal for their special someone.  While enjoying canapés and wine, Chef will help the men prepare a take-home romantic dinner that is easy to put together on Valentine’s Day.  So that no romantic gesture is forgotten, Chef will even provide a to-do list that includes “turn the music on low,” “light the candles,” “set the table,” and step-by-step instructions for final culinary prepping.  Half bottles of red and white wine are included, so the pairings are perfect and worry-free.  Now, for at least one night, your beloved will think you can cook a Two Michelin Star caliber meal!  The cooking class is two and half hours and is $300 per person.

ELYSIAN. 11 East Walton. 312-646-1415.

Suite Dreams with Dom

This Valentine’s Day, sipping bubbly has its benefits, on Monday, February 14th toast to your sweetheart with a bottle Dom Pérignon, and Four Seasons Hotel Chicago will host you for an overnight stay in one of the hotel’s stylish Executive Suites. Sip with spontaneity and surprise that special someone with a luxurious overnight stay on Valentine’s Day. Or if planning is required, sip then save the stay for a future date. Four Seasons Hotel Chicago will offer a gift certificate for a return overnight stay in an Executive Suite, based upon availability.

Four Seasons Hotel Chicago. 120 E. Delaware Pl. 312.80.8800.