https://maps.google.com/maps?q=Chesapeake,+VA&hl=en&ll=36.753224,-76.263957&spn=0.006619,0.011373&sll=27.698638,-83.804601&sspn=7.407541,11.645508&oq=chesap&t=h&hnear=Chesapeake,+Virginia&z=16&layer=c&cbll=36.75348,-76.264223&panoid=D9EpE8OYbUxbv6_SFR4iVA&cbp=12,315,,1,0
This one here I find very interesting. Northbound on VA 168 in Chesapeake, VA; Richmond is signed via I-64 (EB) to NB I-664 instead of its right way of I-64 WB because its actually shorter and more direct this way then to follow the one route only.
I think it is so fascinating the fact that in this rare case, a place is signed opposite of the actual way of direction of where the place literally is. One other place (sort of) is leaving Orlando International Airport where signage on the North Exit signs EB FL 528 for Disney World where in actuality FL 528 EB heads away from Disney totally. Its the Orlando Airport using the road temporarily to reach FL 417 that accesses Disney by looping around to the south of the Airport in an attempt to reduce congestion along FL 528.
Any such other place where a city would be signed in the opposite way of its course?
No actual examples, but a few that get partway there:
In the future, I-41 and I-43 will wrong-way overlap south of Milwaukee. Since both go to Green Bay, any use of this as a control city would be wrong-way on one of the routes (but currently it doesn't seem to be used).
Following the IL 110 Chicago-Kansas City signs eastbound will take you westbound on I-80 near Moline, but signs don't actually point Chicago that way (it's the control city on I-80 east).
Another could-have-been example that might help find similar situations that do work: I-20 west at I-55 near Jackson. If I-55 had significant problems through Jackson that warranted bypassing on I-220, Memphis might be signed with I-20 west/I-55 south.
I-95 north of Trenton almost works similarly to your I-64 example, with signs for Camden via I-95 north to I-295 south. But Camden isn't Philly.
There are probably many examples of this where Interstates intersect the parallel U.S. Route, and you go the wrong way on the U.S. Route to reach the Interstate.
In the southern suburbs of St Louis, Chicago is signed along I-270 north, but the signs tell you that it's in fact quicker to take the I-255 loop instead.
I think that I-270 north needs a different control city.
NB Broadway at 880 in Oakland has a sign directing San Francisco traffic to go EAST on 980. I'm assuming it's a relic of the Cypress Freeway detour.