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How Far Does $1,000 Take You on a Trip to Chicago? We Found Out.

How Far Does $1,000 Take You on a Trip to Chicago? We Found Out.

I have lived in New York most of my life, but I was born in Chicago and I try to get back at least once a year. I was overdue, and so when The Wall Street Journal asked me to see how far I could stretch $1,000 in my hometown, I jumped at the opportunity, though I saw one wrinkle to the plan. I had a physical booked for when I returned to New York, so I introduced an additional catch. I'd eat cheaply—but also healthy. Here's how I fared.
Upon landing, I bought a $15 3-day unlimited public transit pass. An Uber from the airport can cost $100 with surge pricing. On the L train from O'Hare, I zipped past clogged traffic on the expressway.
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