Chicago is a lot more of a fun city with a lot more to do all the time but it does cost more to live there. More activities, more events every week, summertime always has something going on, Chicago sports/social is great year round with co-ed sports leagues being huge there. Fanatical sports city. Many different neighborhoods around the city with different vibes but all right next to each other and walkable, endless supply of fun non-generic places to hang out, No car needed, easy public transit around the city and to the airport via the blue line. You can walk or bike anywhere, you won't be doing that in DFW lol. North Beach in the Summer. More active city by far if you like to keep in shape and that kind of thing.

Dallas is better if you like strip malls, the Dallas Cowboys, chain restaurants, fire ants, driving forever to do just about anything, generic chain bar/grills, or have a family and want to live in a nice house in cookie cutter suburbia for cheap. Uptown/Deep Ellum and part of Ft Worth are ok for fun areas but they are small isolated areas and equivalent to ORD housing prices to be in those areas. There is literally nothing to do in DFW if you live in a suburbia area (which is 95% of the huge sprawling area) but sit around with others and drink beer, watch football and go out on the lake occasionally if you or a friend has a boat. There are some really pretty girls around DFW but the ones in ORD are much friendlier and not as stuck up and materialistic, IMO.

Single, Active = Chicago
Family ready to settle down in suburbia and put the kids in a good school = DFW

I miss Chicago. Winters are long and it sucks, but you can still have fun at least, just indoors. lol.