If you love Chicago, check out Denver. Its not similar in any respect, but I have found a lot of people who love Chicago love Denver.
Seattle is awesome. I take the Seattle or Denver weather any day over Chicago. I cannot stand wind and humidity in the winter.
Really depends on whats important to you and where you can get a decent job though. You'll be able to settle down in the burbs anywhere… the big question you want to know is what is easily accessible to those burbs. Mountains, water, weather, sports teams, entertainment?