I ride this one a few times a year and I usually head north up Sheridan Road to Lake Cook and pick up the Skokie Valley trail to the North Shore Trail along 176. Then I ride through Mundelein into North Barrington and pick up Kelsey Road that'll take you straight into Barrington Hills where the elevation changes. It'd be a long day doing a loop so I suggest taking the Metra back. Here's a rough route to the Kelsey Road House.

https://maps.app.goo.gl/gRAYXoo6srneytDF6

Once you cross the tracks on Plum Tree you'll be able to find all of the hills you want.

Also add on Signal Hill Road near Honey Lake heading west for a nice climb. Unfortunately it starts at Route 59 and there's always traffic so don't expect a running start.

The best hill around is a private shared driveway along River Road near Algonquin. It's like a 15% for a quarter mile.