Chicago's a very nice city. There are basically three main factors keeping the cost low currently:

1. Population decline. 2. A very large amount of good housing stock. Chicago's completely flat with solid public transit reaching out to the suburbs. 3. Lower proportion of tech and startups. Similar to how tech has driven up the CoL in many cities, the relative lack of tech in Chicago has kept CoL down.

Winter is rough in Chicago, but the CoL in Boston has skyrocketed which invalidates that as being the _only_ reason.

Agreed, weather cannot be the only reason. What drives the population decline in Chicago despite the low CoL?

Rising tax burden and fiscal mismanagement. Check out property taxes and the debt Chicago, Cook County, and the state carry.

Your dollars go further in Tennessee, Florida, or Texas (all of which have no state income tax).

Chicago has a huge part (1M+) that's effectively a Rust Belt city like Cleveland, St. Louis, or Detroit. It has deindustrialized and suffered disinvestment, and anyone in that section that has the ability to leave does.

Chicago has a wealthy, top-tier global city of 500k inside a depressed Rust Belt city of 2.5M. There's significantly less economic and population pressure on the core global city.

Such a great place, I try to tell, particularly young people how important picking the right city is. If you pick a bad City, you're going to end up not being able to afford to live your life will be needlessly stressful, you won't be able to find a partner. But if you pick a good city live can be pretty good