Aranjuez is only 50 minutes from the Plaza Mayor in Madrid as is Chinchón. Consuegra is about 1.5 hours away and not far off the E-5. Easy off and back on the highway. Manzanares Is just about in the middle and just under 2 hours from the Plaza Mayor.
I used the Plaza Mayor only as a guide since you didn’t say where in Madrid you’d be departing from. The times from the airport are about the same.
If you stopped at Consuegra for lunch and see the castle and windmills and you had a little more free time, then you could head over to Campo de Criptana to see its windmills made famous in Cervantes’ Don Quixote.
If you opted for Chinchón, you could easily make your way back to the E-5, by Aranjuez, and still stop at Consuegra to see the windmills and castle. Aranjuez is 30 minutes from Chinchón.
Consuegra’s windmills and castle are great to see, while Chinchón’s plaza mayor is very pretty. I’ve never stopped in Aranjuez or Manzanares. I do think Chinchón has more restaurants than Consuegra and there are a couple free parking lots. The town of Consuegra doesn’t see nearly as many tourists since most people just visit the windmills.
I will add that there is no real spectacular scenery along that route. For pretty scenery you’d be better off taking smaller roads and that would require more time.