GA pilot reported possibly flying too close to obstacles during a flight.

Narrative

I was on a flight to see the Chicago skyline with a plan to traverse from North to South along the lakeshore and then turn West to follow the Eisenhower expressway beneath the 1;900' shelf of the O'Hare Class B airspace and immediately to the North of the Midway Class C airspace. I was using the VFR flyway chart on Foreflight for navigation; where the Willis tower is depicted as a 2;325' MSL obstacle more than 4;000' North of the Class C boundary. I intended to pass South of the Willis tower with more than 2;000' of horizontal clearance while remaining clear of the Class C. As I flew the route visually; it appeared that there were other obstacles in between the Willis tower and the Class C boundary that I might not have cleared by 1;000' vertically and 2;000' horizontally.Upon landing; I checked the VFR sectional chart and terminal area chart; where there are buildings depicted as obstacles just West of the lakeshore and on the Class C boundary at 1;381' MSL (788' AGL). These obstacles are not depicted on the VFR flyway chart. Had they been depicted on the flyway chart; I would have flown higher over the lakeshore while remaining below the 3;000 Class B shelf. Since these obstacles/buildings are not shown on the VFR flyway chart I flew at a lower altitude and may not have maintained adequate horizontal and vertical clearance.I should have checked the obstacle database in Foreflight; VFR sectional; and terminal area chart in addition to the VFR flyway chart before following this course. Ideally; the buildings depicted on the sectional and terminal area charts could also be depicted on the VFR flyway chart since they lie along a popular transition route to the West from the lakeshore.