Well they are quite similar aren't they? ... I was introduced through Chronicles, and I do like it because it's got the songs in chronological order (and my fondness for Lakeside Park is a factor) ... but hardcore Rush fans will probably tell you that the addition of By-Tor and Xanadu tips the scale in favour of Retrospective ... (they'd also insist on individual albums) 
So if pushed, I'd say Retrospective ...
Chronicles
Track listing Disc one: 73:47 1. Finding my way (5:05) 2. Working man (7:09) 3. Fly by night (3:19) 4. Anthem (4:22) 5. Bastille Day (4:37) 6. Lakeside Park (4:07) 7. 2112: overture / Temples of Syrinx (6:44) 8. What you're doing (live) (5:38) 9. A farewell to kings (5:21) 10. Closer to the heart (2:53) 11. The trees (4:38) 12. La Villa Strangiato (9:34) 13. Freewill (5:23) 14. Spirit of the radio (4:47)
Disc two: 69:03 1. Tom Sawyer (4:34) 2. Red Barchetta (6:08) 3. Limelight (4:20) 4. Passage to Bangkok (live) (3:45) 5. Subdivisions (5:32) 6. New world man (3:40) 7. Distant early warning (4:56) 8. Red sector A (5:10) 9. The big money (5:34) 10. Manhattan Project (5:04) 11. Force ten (4:32) 12. Time stand still (5:08) 13. Mystic rhythms (live) (5:40) 14. Show don't tell (5:00)
Retrospective I
Track listing 1. The spirit of radio (4:56) 2. The trees (4:42) 3. Something for nothing (3:59) 4. Freewill (5:21) 5. Xanadu (11:04) 6. Bastille Day (4:37) 7. By-Tor and the snow dog (8:37) 8. Anthem (4:21) 9. Closer to the heart (2:51) 10. 2112: overture (4:17) 11. temples of Syrinx (2:13) 12. La Villa Strangiato (9:34) 13. Fly by night (3:21) 14. Finding my way (5:06)
Retrospective II
Track listing 1. The big money (5:34) 2. Red Barchetta (6:08) 3. Subdivisions (5:32) 4. Time stand still (5:08) 5. Mystic rhythms (5:53) 6. The analog kid (4:46) 7. Distant early warning (4:56) 8. Marathon (6:39) 9. The body electric (4:59) 10. Mission (5:46) 11. Limelight (4:21) 12. red sector A (5:09) 13. New world man (3:41) 14. Tom Sawyer (4:34) 15. Force ten (4:31)
------------- "Death to Utopia! Death to faith! Death to love! Death to hope?" thunders the 20th century. "Surrender, you pathetic dreamer.”
"No" replies the unhumbled optimist "You are only the present."
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