It was a little after 2. a.m. one Friday morning two Novembers ago when I found myself on the Red Line train, on the North Side of Chicago, though I had been all the way north and south a few times already that night. I was tired, a little cold, and things were getting sketchy. I'd never been on the “L” that late before, and my plan to ride all night was seeming less and less safe the more stops we made. My car was empty, finally — the only other passengers had been two drunk men who kept asking where I was going and if they could come — and at each stop I tensed up, hoping no one else would get on.
It was a far cry from the private bungalow in Bora Bora where I had been just 24 hours earlier, but extreme contrasts were becoming the story of my life. I'm a freelance travel writer, which means I get to visit amazing places and stay in some of the world's most beautiful hotels. It also means I don't make very much money, thanks to rapidly decreasing magazine rates; so to afford my apartment in Chicago, I used to rent it on Airbnb while I was gone, which was often. This worked well. Too well, actually. So well that I found it hard to turn down guests even when I was in town.
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