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The software that I have mentioned till now do a pretty good job in converting CHM to PDF. But if you already have a virtual printer software installed, then you can actually use them to do this conversion. One such software is doPDF. It is a simple and easy to use PDF making software. You can also use it to create PDF from CHM (Compiled HTML Help File) files. First install this virtual PDF printer in your PC. Now you can open the CHM file and go to the top most level of the "Contents" of this help file. Now you can click Print button on the toolbar and choose "Print the selected heading and all subtopics" from the shown dialog box. You can click OK and choose doPDF from the printer list.
After selecting the doPDF as printer, you can control various useful settings by clicking Preferences button. Here you can change the page size of the output PDF by choosing from Predefined page size list or by applying the custom Width and Height. You can change the Orientation of the pages, like Portrait or Landscape. Graphic Resolution can also be controlled in dpi (Higher the resolution, higher the quality, but big file size, similarly lower the resolution, low quality, but small size). There is a scaling option also present with resolution setting and you can control it percent wise of the original.
After making the desired changes, you can click Print button and browse for a location and give the name to PDF and click OK button to start creating PDF file. Your converted PDF will open automatically after conversion if you check "Open PDF in reader" button. By using doPDF, you can convert almost any type of printable document into PDF. Home Page Download Page
PDF24 Creator is another PDF Printer in the list that lets you convert CHM to PDF. It works in exactly the same manner as doPDF, that I explained above. Just open the CHM file and go to the topmost level of the Contents. Click Print button on the main toolbar and choose "Print the selected heading and all subtopics" from the radio button. Now choose "PDF24 PDF" as a printer from the Printer dialog box. Just click Print button if you do not want any additional settings.
If you are an advanced user or want to control more settings, then you can click Preferences button after selecting the above said printer. Here you can choose layout tab to apply settings like Page Orientation (Portrait, Landscape, or Rotated Landscape), Page Order (Front to Back or Back to Front). Pages per sheet can also be controlled (from 1 to 16).
For more settings, you can click Advanced button. Here you can control Paper Size, Graphic Quality, Scaling, Color Management and many more. You can click OK to apply the changes and finally click Print button. Now PDF24 Assistant dialog box will open. You can click "Save as PDF" button to start saving the PDF file in the desired location.
Further more if you want to control the PDF properties, like: Meta Info, Compression, Resolution, Security (Password to open, Encryption, Signature etc.), then you have to click "Save As" button instead of "Save as PDF" as stated above.
This PDF Printer also supports creating of PDFs from almost any printable document. Home Page Download Page
arCHMage is the most complicated CHM to PDF software in this list, and meant for geeks / developers only. It is a completely command line software that needs Python to run. It is basically a CHM decompiler that comes with option to compile contents of CHM into some other format. So, you can use it decompile CHM to HTML, and then compile the HTML contents to PDF. Apart from Python, you will also need PyCHM, BeautifulSoup, etc. You can see complete list of dependencies here. Due to my lack of knowledge of Python, I couldn't try it out. If you are one of those who was able to make it work, do share your feedback in comments below. Home Page Download Page