Some of the ugliest looking district ducklings are beautiful swans in the eyes of the courts. For example, the Illinois 4th Congressional District drawn in the 2000's decade is often called the "earmuff" district for obvious reasons. The western portion of this district actually travels along the northbound lane of Interstate 294! But, this district has a very important purpose. It was initially created in the 1990s to elect the first Latino representative to Congress from the Midwest.

The 4th congressional district has its funny shape because there is an African-American community sandwiched between two Latino communities. The African-American community is represented by the 7th Congressional district, which is designed to elect an African-American candidate of choice. The 4th district was wrapped around the 7th district so that both African-American and Latino communities could have congressional representation.

The Chicago example is famous, but the case earlier this year with several districts in North Carolina revolved around race and disenfranchisement (as partisan gerrymandering is common and exceedingly difficult to make unconstitutional). These were created in a partisan way, but with hopes that it would be within the law. In any case replacing North Carolina's districts algorithmically without respect to race would be illegal.

Some background https://ballotpedia.org/Majority-minority_districts