Harry & Sally leave for Florida by car from The University of Chicago which is on the south side of the city. The very next scene shows them driving southbound on Lake Shore Drive approaching The Drake Hotel which is on the north side of the city.
To drive to Florida from the South Side of Chicago, one would head south; not drive 8 miles north and then turn around and go south again.
Correction: They went to New York. However, the same comment applies. To get to New York from The University of Chicago, you STILL would head SOUTH since you would need to drive south of Lake Michigan to go EAST to New York.
You WOULD NOT drive 8 miles north on Lake Shore Drive and then turn around and go south again.
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