Which scores should I send?

My superscored SAT is a 2200: 680CR 760M 760W, single sitting is a 2130 with the writing as a 690 but CR and M the same. My ACT is a 33: 34E 33M 33R 33S.
Should I send both SAT and ACT or just ACT?

My main conflict is that i think only CR+M is primarily considered by UChicago and mine is a 1440 which is near the 25th percentile, but my writing is at a good percentile and they consider it supplemental. My ACT however is more towards the 50th I think.

Send ACT only if they do not consider writing for the SAT. If they do consider writing, you can send both. A 33 is about a 2200 (I think its actually 2180-2220). Sending only the ACT score is probably good enough (not to get you in, but to gravitate the adcoms focus away from numbers and to essays and ECs).

They don’t consider writing at all.

My understanding is that the writing score doesn’t matter, so you might as well save yourself money and just send the ACT score.