Which Software Converts Chm To Pdf With Bookmarks?

I like simple, reliable tools when I need bookmarks to survive the trip from CHM to PDF. If I’m lazy I open Calibre, import the CHM and convert while ensuring the Table of Contents options are set — Calibre often keeps the TOC as PDF bookmarks and it’s cross-platform, so that’s my default first try. When Calibre messes up the structure, I extract the CHM contents with 7-Zip and then use wkhtmltopdf or run the HTML through pandoc to produce a LaTeX/PDF build that properly generates bookmarks from headings.

A handy middle ground: kchmviewer on Linux can export to PDF and sometimes preserves the TOC, so it’s worth a quick attempt before doing full extraction. Avoid using a virtual PDF printer if you need clickable bookmarks — those typically flatten the outline. In short: test Calibre first, then chm2pdf or an extract+wkhtmltopdf/pandoc pipeline for the most faithful bookmarks, and remember to spot-check the PDF in your reader to confirm the outline looks right.

Okay, here’s what I usually reach for when I want a CHM to PDF conversion that actually keeps a usable bookmark/outline: Calibre, chm2pdf (the CLI tool), and a two-step extract-then-render workflow with wkhtmltopdf or pandoc. I tinker with ebooks in my free evenings, so I’ve tried the sloppy one-click printers and the fancier approaches — the difference shows most when you need the PDF outline to mirror the CHM table of contents.

If you want something simple and cross-platform, try Calibre. Import the CHM, then use Convert books → PDF and pay attention to the “Structure detection” / “Table of contents” settings: tell it to build the TOC from the CHM’s built-in navigation or from headings. Calibre often writes that TOC into the PDF as bookmarks, though you should always check the resulting file in a PDF viewer. For a more deterministic result on Linux, the command-line tool chm2pdf (usually in distro repos) is made specifically to convert CHM into PDF and can preserve the CHM TOC as PDF outlines — check your package docs for the exact flags on bookmarks.

If you want full control and don’t mind a longer route, extract the CHM contents (7-Zip or extract_chmLib), then render the site to PDF with wkhtmltopdf (it has options to create an outline/toc) or run the HTML through pandoc to LaTeX and export with hyperref so the TOC becomes PDF bookmarks. This takes more steps but gives the best fidelity and lets you fix CSS, fonts, or broken links first. Quick tip: always verify encoding and images after conversion, and if the CHM is huge, split sections before converting to avoid memory issues.

Short version: multiple tools work, but my go-to choices are 'Calibre' for convenience and 'chm2pdf' or an extract+wkhtmltopdf flow for reliability. I’m the type who prefers the command line for reproducible results, so I’ll sketch a clean workflow.

First, try Calibre if you want a GUI and quick results. It usually preserves a TOC that becomes PDF bookmarks if you configure the conversion settings under Structure/TOC. If you’re on Linux or comfortable with terminals, install chm2pdf from your package manager — it’s designed to convert CHM to PDF and can export a PDF outline matching the CHM navigation. If chm2pdf isn’t available or you want more control, extract the CHM files (7-Zip or chmlib tools), tidy up the HTML/CSS, then use wkhtmltopdf (or pandoc → LaTeX) to generate a PDF with an explicit table-of-contents that becomes bookmarks. Note that printing to a PDF printer often loses bookmarks, so avoid that method if outlines matter. Also watch out for special encodings and embedded fonts — those are usual troublemakers.