Why make Chicago another state? Why not cede it to Venezuela as its capital? They are both in the same financial straits
2016 Election:
Illinois voted as it usually does, with a pronounced Chicagoland/downstate split. Though the majority of Illinois appears to be Republican. Cook County and the six collar counties hold 65 percent of the state’s population. The area’s dense, primarily Democratic population brought Clinton ahead by more than 800,000 votes. Cook County held the largest margin for Clinton, where she outperformed Trump by more than 50 percentage points. On the other end, the county with the largest percentage of Trump voters was downstate Wayne County, where more than 80 percent of voters chose Trump.
See Map @ link
https://www.chicagotribune.com/data/ct-illinois-president-results-20161108-htmlstory.html
If there was only a way to force California on Mexico since they are at least 75% Mexican anyways
Or they could simply run candidates in all of the races. The Democrats ran unopposed in roughly 1/3 of General Assembly seats.
Hard to control the state when you give up that many seats.