Ted Greene wrote a couple of good books for jazz chord progressions, as well as Chord Chemistry which is a long project to master.
Learning tunes from The Real Book - standards like Autumn Leaves, All Blues, Equinox, Freddie Freeloader, etc, is a good start.
Other useful things to learn:
- Rhythm Changes - "I Got Rhythm" was a huge hit in the 1920s and a large number of jazz standards are built on those changes - including "The Flintstones." Learn rhythm changes and you'll know enough for lots of songs - "Ain't Misbehaving," for example, is rhythm changes at root. It expands your repertoire pretty fast
- Learn some jazz blues with complex turnarounds. Start with something straightforward like "Stormy Monday" which, while not dead simple, has a very comprehensible pattern and turnaround which is different from V-VI-I. "Freddie" will also help here, as will Monk's wonderful "Straight No Chaser"
- Learn how to use passing chords. Rather than playing A-7, D7, Gmaj7 (for example), play an A-7 to D7#9 to d7b9 to G7.....the two D chords add some voice leading for helping tune up your ears and hands.
And listen to solo Joe Pass and Lenny Breaux to get an idea of what is possible.
This is just the barest start and is chord-focused rather than solo-focused but I hope it helps.