New to Roadtrip America... looking for help!

I'm a writer, researching an overnight roadtrip from Boston to Chicago. (This is for a work of fiction.) I've driven this route during the day but never at night, and I'm looking for help with some memorable landmark someone might have seen at night or other special considerations for this route at night. The driver would prefer not to be seen (why she's driving at night) but is not on the run. So she can/will stay on I-80 and I-90 for the fastest trip possible.

Any help with rest stops, bridges, buildings, light features, etc., that someone would especially notice at night along this route would be most appreciated!

Thank you,
JM