Chicago

Pros:

- Beautiful lakefront, architecture, & parks

- Dense, walkable, & easy to get around by train or bike

- Tons of cool things to do & people to meet (festivals, concerts, meetups, clubs, museums)

- Relatively inexpensive, especially compared to NYC or LA

- Within driving distance of my midwestern family

Cons:

- Car traffic is often bad (I don't drive in the city)

- I often have to switch CTA train cars because of people smoking on the train

- Winters are cold (I'm used to bundling up)

- Property tax rate is relatively high