IMHO SimBrief is not always correct. The routing SimBrief has given you is strange. The STAR route exit is in the opposite direction of the ILS approach entry. This means the aircraft flies by KORD outbound, turns around, flies back over KORD to the ILS entry, and then turns around again to enter to ILS. Try calculating the TOD with all these turns! This even looks strange to me on the SimBrief pdf map.
This route is imported and loaded into the 787 FMC as-is. And the autopilot will fly the aircraft as directed.
To “fix” this route, in the FMC I deleted the STAR, added waypoint BYLAW after RYELY, and deleted the discontinuity. The TOD was recalculated to descend from 37,000 ft to 9,000 over 96 nm which seems about right.
I always compare the SID, STAR, and approach charts to the flight plan. Does everything make sense? Would I plan the route differently?
I have no idea WHY SimBrief chose the routing it gave you. I think SimBrief (and SkyVector) use a different flight planning algorithm not used by other flight planners. It chooses the most recent routes flown IRL between the departure and destination. These routes would reflect any weather or ATC traffic flow routing which may not be the optimal time or distance. The various flight planners are good tools for creating routes but they always should be checked using the actual charts.
Both in MSFS and IRL the ATC climb/descent instructions often do not match the calculated VNAV path. In general, the pilot has to decide to fly according to ATC instructions or to VNAV although the climb/descent speeds are used for fuel economy and engine efficiency.