So from watching the latest trailers and footage, there's apparently mountains and hills in Chicago, all of which are visible from the city. As a Chicagoan, this baffles me. But I guess that answers my question considering there are not pilot-able flying vehicles.

Maybe The Taste of Chicago takes place during Watch Dogs, cutting you off from the Lake Front. Not because of the crowds of people, but because you'll get stabbed and mugged for your tempura shrimp.

GeoMod 2.0.

They just have an infinite loop a la the Matrix subway.

"I still have work to do here"

I'd love it if, at the edge, his hat flies off and he automatically runs back to grab it.

Alternatively, sharks always work. Just spawn a shark in the middle of the road. Or a literal watch dog that does that "I'm watching you" gesture with his paw. Not sure how that would stop you, but combine it with the hat and shark ideas, and you're golden.

That is genius.

Hackers

giant horrific Dave Lang face at each cardinal point

I agree. It's silly. It's one of the things that makes GTA feel like a cartoon wanting to be taken seriously.

Hey, this topic exists! What the hell! Why are there mountains and why is Chicago an island that lacks its Northside? I want Wrigleyville, damnit!

I think it's just that Chicago has not been represented very often, so I'm all exicted and then it looks like it's surrounded by the sierra nevada. There are so many better solutions than this....

The Northside has been flooded by global warming. And then they had to build a dam and wind turbines. And the continental plates shifted, causing mountain formations.

Not really. It seems like they just got the basic gist of downtown and determined that the rest of Chicago was too flat and boring to explore. I mean, I'd be fine with them just recreating downtown if they had more key landmarks. I expected the Art Institute to be there, but nope. None of the museums seem to be there. No field museum, planetarium, or aquarium. Museum of Science and Industry would have been a cool place to set a mission. It has tesla coils and mini tornado/wind vortex simulators! It would have been nice to see a Chinatown in their version of the south side as well.

I'm kinda disappointed, but it's still a fun and intricate city to explore, even if it is an inaccurate recreation.

@minipato: Sucks to hear it's not exactly accurate :/ Still love the game though