We made the jump from the East Bay to Northern suburbs with 2 grade school kids in 1990! I will just make a couple of general thoughts. While Lake Forest and Deerfield are nice areas, you pay a premium to be on the east side of 294. There are many good school districts on either side of the highway.
The closer you live to a Metra train station, you will also pay a premium for- Barrington, Palatine, Lake Forest, you will pay a premium. If your work will put you downtown, you definately want to be closer to a train station, but no reason to pay the premium if that is not in the cards.
Last, be VERY aware of property taxes- We pay $13,000 in 60060 and it tends to trend up every year. Lake County, many feel, is a better zip code than Cook County.
Best of luck! We would move out of IL in a heartbeat if all our kids and grandkids where not settled very close by.