Because every man needs a plan, and some of us need that plan with a flowchart, we present Where to Take Her: a series that answers a gentleman's most pressing lifestyle questions and recurs whenever we get around to it. This go-round: The Local Holiday. Do it to it.
Hilton Hotel – South Loop – All out, you say? Aim your sights atop the Hilton Hotel to the Conrad Hilton Suite — a palatial two-floor manse so grand it has its own helipad. Recently renovated to the tune of $1.8 million. Moneyed flourishes throughout. A well-appointed library with a billiards table. Lakeview balconies. A baby grand piano, natch. And a winding staircase that brings you downstairs to three private sleeping dens. Price tag: $10K a night.
Langham Hotel – River North – A Club Level Suite Room gives you exclusive access to the hotel’s butler service and the 12th-floor Club Lounge. Worth it. You can’t go wrong with the Mediterranean eats at Travelle. And Chuan Spa — just awarded Chicago’s only five-star spa rating by Forbes Travel Guide — is always a welcome respite. All of this amid a mid-century modern aesthetic that would meet the high standards of even the dandiest English gent.
Loews Hotel – Streeterville – The newest hotel to grace our skyline (opened yesterday), the Loews offers spacious rooms with impeccable modern taste. Close enough to Downtown without the bustle. Why you’re really here: splurging at Rural Society, the hotel’s Argentine steakhouse helmed by Iron Chef Jose Garces. The wood-fired grill fills the dining room with the smell of sweet wood. Wine list leans South American.
The Peninsula – Gold Coast – Classic luxury. One of the best spas in the city. That’s The Peninsula. We particularly love their premium treatments because they take place way up on the 19th and 20th floors. Means peace and quiet. Indulge in full body scrubs and the Pen’s much lauded aromatherapy massages. Make it a full-day journey.
Soho House – Fulton Market – The always entertaining Soho House is the perfect answer if you frequent Randolph Street. Besides access to members-only areas like the fifth-floor bar and rooftop pool, every room comes with Cowshed toiletries and Marshall Stanmore speakers. Plus: you’ll not want for action — there’s always something happening ‘round here.
Virgin Hotel – The Loop – When you fly, luxury takes form in the little things. The details. That’s basically the country’s first ever Virgin Hotel in a nutshell: everything’s made with the traveler in mind. Bluetooth soundbars. Bedside clocks that project the time on the ceiling. Televisions that control everything from room service to the thermostat. Room bars stocked at street prices. Like flying First Class in your own city.
Waldorf Astoria – River North – Tucked away in the Waldorf you’ll find The Elysian, a polished spa retreat where you can treat her to a deep-tissue massage and mud treatments while perusing a full roster of treatments geared just for the fellas. The property itself: all things you’d expect from a luxury hotel, minus the snobbishness.