Earlier quoted context omitted.
Chicago is having significant population loss, so that gap will only grow. I believe Houston is about to pass Chicago.
Why is Chicago losing people?
Houston has seen tremendous growth primarily through annexation. It is now more than 3 times the geographical size of Chicago. But annexation of residential land in Texas is now far more difficult, so the geographic size growth of Houston has dramatically slowed [1]. Once all the undeveloped land is used, Houston will have to rely on densifying for population growth. Current restrictions make it unlikely to ever be as dense as NYC, Chicago or LA, but with its massive size it wouldn't need to be to attain 5 or 6 million residents. On the other hand, it is already facing growth challenges that may reduce the carrying capacity of the city [2].
I'd guess that Houston surpasses Chicago in population within 15 or 20 years, but it remains to be seen if that is going to be permanent or not.
[1] https://www.houstontx.gov/planning/Annexation/docs_pdfs/Hous...
[2] https://www.houstonchronicle.com/news/transportation/article...