Meadowhawk dragonflies are found in a number of places in Chicago. You can read more about them at UW Milwaukie's Field Station website; they were actually a featured "bug of the week" there.
Also, here's a video taken of one at the West Chicago Prairie Nature Preserve:
Meadowhawk Dragonfly at the West Chicago Prairie Nature Preserve from Bill on Vimeo.
Sightings
(1) Andersonville (8/1/14)
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(Creative Commons Attribution Share-Alike license)
I found a meadowhawk dragonfly in the Andersonville neighborhood of Chicago.
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