IT’S hard to decide, while sipping a citrine cocktail called Sex on the Roof, what to gawk at first: the go-go dancers in crimson panties or the tallest building in the Western Hemisphere, Willis Tower, soaring like a giant glass beanstalk just beyond the windows. Either way, at Roof, the glossy club atop theWit hotel in Chicago, if you’re single you can’t lose: should a stranger fail to take your breath away, the skyline will.


As an architect’s daughter (one who built a foam core replica of a Frank Lloyd Wright house when she was 12), I’d long wanted to visit Chicago, where Wright buildings are practically as common as pizza joints. As a veteran solo traveler not content to turn in early, a spate of posh new boîtes was a bonus.


Of course, parachuting into a major city on one’s own has its perils. It’s not like lolling on a beach or rafting through the Grand Canyon. In a city, there are dodgy neighborhoods, dodgier men and jammed bars and restaurants where you’ll be parked at a table for one. Chicago, though, is hardly as high-voltage as Tokyo or New York, even though it still has the big-city qualities solo travelers crave: culture, night life and a mass transit system to explore it all. It even has white sandy beaches beneath all those skyscrapers. Indeed, friends had described Chicago as a more leisurely and hospitable New York, a city where getting into some hot spots is a breeze compared with lining up outside clubs in Manhattan’s meatpacking district.


Not that I don’t love my hometown. But a little more hospitality wouldn’t hurt. Having spent the winter slogging through a dizzying calendar, it was time for a change of pace. I packed a bag and grabbed my iPod, already loaded with Frank Sinatra. Chicago was calling.


I ARRIVED on a chilly spring evening, wondering why I hadn’t chosen Miami. There was rain. There was wind. Yet outside my hotel, there were dashing porters with umbrellas and bright smiles.


Swoosh! They opened a door and I was inside theWit, instantly warmer but taken aback by the man perched on a tiny balcony high above my head, strumming a guitar like a folk-rock angel. This nearly 300-room Doubletree by Hilton, with a lightning bolt zigzagging across its exterior and jam sessions in the lobby, sure doesn’t feel like a Doubletree.


Opened in 2009, theWit bills itself as a splashy party stop amid the downtown bustle — advertisements for Roof show women in bikinis and stilettos, and bare-chested men brandishing Super Soaker water guns — precisely the kind of place I typically avoid. But my curiosity about this much-ballyhooed club won out. And you can’t beat the location. Sure, I could have stayed in the tony Gold Coast amid lavish town houses, or in artsy Wicker Park with its laid-back bars, or in another of the city’s dozens of neighborhoods. But since this was my first visit I chose the Loop, a constellation of theater, night life and shopping in the heart of Chicago, near Millennium Park, the Art Institute and public transportation.


It’s here, at the State and Lake Street rail station, that you’ll find theWit. At the front desk the staff was so friendly I suspected they were overcompensating for some unpleasant news they were about to spring. But all I got was a warm cookie and a key. Even later, when I gravely pointed out that I had been charged for the minibar “intimacy kit,” which I did not use (really), the fee was removed with a smile. The geniality was almost unnerving.


My king room, reasonably priced for downtown Chicago at $229 a night, was airy and modern, with a bird’s-eye view of the nearly six-story vertical C-H-I-C-A-G-O Theater marquee. Speaking of birds, I feared that one was trapped in the hallway, but it turns out that chirping is piped in through speakers. I swear I also heard frogs. Or crickets. It was oddly soothing, like the iPad app I use for insomnia. While such touches are fun, I was there for convenience, including easy access to Roof — my first stop.


There on the 27th floor was a smattering of casually dressed couples and klatches of friends. No half-naked women. Yet.