The situations cannot reasonably be compared legally. In Wynn v. Vilsack, a motion for preliminary injunction was granted (and the program was not ruled unconstitutional). In the ruling, the court found that the evidence "does not support a finding that USDA continues to be a participant, passive or active, in discrimination", and does find that there were past successful remediation efforts, thus "the Court expresses serious concerns over whether the Government will be able to establish a strong basis in evidence warranting the implementation of Section 1005's race-based remedial action", moreover "Plaintiff has convincingly shown that the relief provided by Section 1005 is not narrowly tailored to serve that interest". The court finds that there is a good-enough case that the law fails strict scrutiny. Incidentally, Congress repealed that law.
On the other hand, in Evanston, we have no facts or concrete legal allegations (e.g. drafts of a legal complaint). The cited memorandum is a recommendation, not a law. There does exist at least one available council action from 2019 which says that
The Chief Financial Officer is hereby authorized to divert all adult
use cannabis funds received by the Illinois Department of Revenue for
sales of adult use cannabis to a separate fund in a City account for
local reparations. SECTION 3: The City may receive donations to this
fund from separate organizations, corporations, and individuals
established herein by the City Council.
The city also has a page referring to Ordinance 102-O-20 (not available) indicating that "The Committee will work with residents, City staff and experts to explore and identify programs and opportunities to be supported by the Reparations Fund". The Program Guidelines §3 indicates that a person may be eligible for money if they are an ancestor, direct descendant, or "other" who has suffered from a "City ordinance, policy, or procedure that served to discriminate against the Applicant in the area of housing". It thus does not exclude Asian and Hispanic homeowners, LGBTQIA2S+, Catholic, Muslims or anyone else, except insofar as a Catholic was not demonstrably the victim of such discrimination. The city also provides an extensive historical study of past government discrimination in housing. You may be able to eke out more concrete information on what they have done here, at the reparations committee website.
In terms of potential differentia between the USDA program and the Evanston program, the most obvious difference would be in terms of prior remediation efforts. If you sue Evanston for their program, they could defend the program as providing the remediation that justifies the program – which had already been provided in the USDA program.