I have no idea on the 787 but I hear the 777 box is about the same as the 744. On the fix page, can you enter ORD/5 and then get a 5 mile circle around ORD? Then enter 3000 on R6 and it shows you where along your path you'll reach 3000?
Most of the time leaving there I'll do a close in NADP. And in the summertime I'll just tell clearance we'll be unable the restrictions.