If you don't mind a podcast or two, you can get a lot of context from these: Stephen West's "Philosophize This!" as the light-weight option, and Peter Adamsons' "History of Philosophy Without Any Gaps" as the more academic option.

Both go chronologically, from pre-socratics onward. West's podcast is a bit rough in the first episodes, but it keeps getting better.

If you are American I would recommend “Democracy in America” by Alexis de Tocqueville. Very easy to read and has some really mind opening lines. “Americans are cartesians without ever having read Descartes” still sticks with me to this day and I last read it over ten years ago.

I generally don't like summaries, as you just get a contemporary interpretation of what the translator/academic thinks the philosopher was saying. Far better to go straight to the source.

Eventually you'll need to read the original works, but I'd recommend starting with philosophical fiction. Crime and Punishment, The Plague, Zen and the Art of Motorcycle Maintenance, etc. Plato's dialogues are pretty readable, too, as is Thus Spoke Zarathustra by Nietzsche.

I think in many cases the old philosophers are still very readable, but make sure you get a modern translation. Publishers like to reprint 60-100 year old public domain translations, which often makes the material very inaccessible. Get a good copy from a still-breathing translator of anything like Plato and You'll likely enjoy it. Other more modenish ones:

Descartes - "Meditations"

Rawls - "lectures on the history of moral philosophy"

Or some modern ones like Alain de Botton

I found "on the suffering of the world" by Schopenhauer to be eye opening, especially his thoughts on death.

I very much enjoy Richard David Precht for a nice summary of philosophy with ancient and modern context.

The Problems of Philosophy by Russel is maybe useful here.