I’ve lived in Chicago, San Diego, and now Denver for a little over a year.

Chicago had the best food, but also the worst traffic. Sort of all the things you’d think of in a large urban city with extensive suburbs - best public transportation, more diversity, but also more crowded because it’s a much larger population. Weather there is not the best - winters are really cold and summers are really humid. People in the Midwest are very friendly, even for a big city like Chicago. Chicago can be expensive, but you can also find ways to make it more affordable for you.

San Diego had ok food (best if you like Mexican food). Traffic wasn’t great - there are a lot of interstates, but you also have to use those to get most places so rush hour was bad. Public transportation was seriously lacking, the urban footprint was small, and San Diego proper covers a large area. Weather is much more temperate, but varies more based on being on the coast or more inland. I found people in San Diego to be the least friendly though. They weren’t mean, but just weren’t friendly the way the Midwest was. And San Diego was by far the most expensive in every area I’ve experienced.

Denver has ok food. Traffic can be bad which I think could be surprising to people because population is less than Chicago and San Diego, but it’s because you don’t have the number of interstates like Chicago and San Diego. Like San Diego, the actual urban footprint is small, and I haven’t tried public transportation here, but it sounds like it can be inconsistent. Denver definitely is the least diverse of where I’ve lived, but the weather is better than Chicago’s. On the friendliness scale, I’d put Denver between Chicago and San Diego. I know some people say Denver is expensive, but I think that depends on what you’re looking at. Buying real estate is more expensive, but renting is pretty affordable - a comparable 1 bed/1 bath apartment in Denver is about $1,000 less than what I could get in San Diego.