It is actually about a 3 hour drive from central Chicago to Madison. It is 90 minutes to Milwaukee and 90 minutes to Madison from there.
The cost of living is reasonable. Property tax is high in Wisconsin. The state sales tax is 5.5%. The state income tax is progressive. The nearest major airport is Milwaukee's General Mitchell. The biggest airlines are Southwest and Delta. The other airlines are OneJet, American, United, Frontier, Allegiant, Alaska, Volaris, and Air Canada. MKE is so much easier than ORD to navigate.
Since you are not near Lake Michigan, it is colder and more snowy than Milwaukee but it is nothing horrid. The lake keeps the area warmer in the winter. Since we are west of the lake, no major lake effect snow. Michigan gets tremendous lake effect snow.