I think you might just need to tell Skyline to extract chromatograms.
You can use the "File > Import > Results" menu item to tell Skyline to extract chromatograms from raw files.
If you do "File > Import > Peptide Search" the import peptide search wizard guides you through creating a spectral library, importing a FASTA file, and then extracting chromatograms.
If I remember correctly, "Import Assay Library" is almost the same as "Import Transition List" except that you also end up with an iRT database. You still need to tell Skyline to extract chromatograms.
If these instructions were not helpful then you should send us your Skyline document.
In Skyline you can use the menu item:
File > Share
to create a .zip file containing your Skyline document and supporting files including spectral libraries, iRT databases and extracted chromatograms.
Files which are less than 50MB can be attached to these support requests.
You can always upload larger files here:
https://skyline.ms/files.url
-- Nick