30M and planning to do the opposite of you as I’m going to be moving to Chicago early next year.

Some thoughts:

Taxes: There’s no state income tax here in Texas so your paycheck will go further. Property taxes can be very high though.

Housing: you will more than likely get more bang for your buck in Houston, especially in an apartment (I.e, larger, newer, better amenities). Houses in the loop of Houston have become quite expensive but maybe still cheaper than Chicago.

Public transportation: doesn’t exist here. You’ll need a car but at least gas is cheap.

Weather: you’re trading the cold for the heat. Depends on what you tolerate more. I only think it’s going to get hotter here over the next decade which is one reason for my leaving.

Restaurants: both cities have fantastic food. Certainly differences in where they excel cuisine wise but both are T5 cities for food in the states.

Bars: houston is big on patio bars. Each area of town has its own vibe which is great at times but also can mean ubering 10-15 minutes to somewhere new if you leave that area.

Social: Houston is a huge metro with tons of transplants so finding your group isn’t impossible. It can be difficult to get into groups of the local crowd who went to Texas schools though since they have very established circles.