I loved Indian Trail as a kid - my aunt waitressed there (long story associated with that, which I won't go into).
That space is now La Bella Winnetka, a good Italian place with one of the most outgoing, entertaining owners you'll ever stumble upon anywhere.
La Bella Winnetka
505 Chestnut St.
Winnetka
847-441-6002
For American, my go-to place in Lake Forest has always been South Gate Cafe - especially if the weather's nice, the patio is a great place to dine.
South Gate Cafe
655 Forest Ave.
Lake Forest
847-234-8800