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

I took a seat. Panoramic views from the deck and floor-to-ceiling windows made it easy to be simultaneously present and miles away. Gazing out at Marina City’s towers, rising like two corncobs (as the locals call them) from the banks of the Chicago River, I daydreamed about what it might be like to live there. Had I peered through the telescope, I might have lingered even longer, zooming in on one real estate fantasy after another.

On a different evening at Roof, this time well past midnight, two go-go dancers twirled like woozy tops, flanking a D.J. who was blasting Paula Abdul’s “Straight Up.” It was more lively than the night I arrived, which suits the space: it’s too sprawling for tête-à-têtes. Still, I later wondered aloud to a man I met why a lounge with fire pits, a 12-foot-wide HDTV monitor, and million-dollar views felt it also needed to throw in a couple of dancers in panties.

“Are you visiting from New York?” he asked.

I nodded.

“It’s the Midwest,” he said. “Welcome.”

JUST because you travel to a city on your own doesn’t mean you have to explore it on your own. One often overlooked way to connect with other solo travelers is to join a MeetUp group. For the uninitiated, MeetUp is a Web site through which people with shared interests can participate in free local activity groups all over the world. During a recent week in Chicago, there were more than 1,400 MeetUps, including ones offering happy hours, beach volleyball and live jazz. If I could have squeezed it into my itinerary, I would have attended a Windy City Explorers MeetUp, which organizes visits to different neighborhoods and historical sites. Or I might have tried 312 After Hours Nightlife Social Scene, whose coming events include an after-work party at a W hotel, an art walk and a wine tasting. Another popular MeetUp, MingleAround, is specifically for singles.

Offline, Chicago goes the extra mile to help tourists get their bearings (something Los Angeles and other sweeping cities would greatly benefit from doing). The Chicago Greeter service, for instance, provides free personalized tours of a neighborhood or special interest (food, African-American heritage, gay-friendly areas), but, sadly for me, requires reservations at least 10 days in advance. So I thought I’d try the next best thing: An InstaGreeter, the Ramen Noodles of tour guides. Local volunteers, they lead free hourlong walks, no reservations required.

Unfortunately, I arrived at the Chicago Cultural Center’s Visitor Information Center, home of the InstaGreeter, to discover that he or she was out on another tour. Luckily, exploring Chicago on your own is not like wandering around Turks & Caicos, my previous solo adventure: no one looks at you sideways when you dine alone, and there’s more to do than stick a straw in a coconut and work on your tan.