Where are you guys from?

As far as outdoors, Chicago's offerings are pretty basic: our parks and beaches are nice, and you can find a bike tour or two, but you wont find any mountains or wild and crazy trails to explore.

Here are two hipster recommendations for you:
Wicker Park = roughly the Portland of Chicago. Food. Good bars, hipsters. Some stores.

Pilsen = The Mission (SF) of Chicago. Mixed community, good interesting food, lots of artists and some stores as well. I can elaborate more on those if you would like.

For Mosquito:
Favorite bars/restaurants: Big Star (Wicker), Simones and Skylark (Pilsen). Violet hour is good though a bit overrated -- and expensive. DMK in Lakeview is good, and Kumas is good though the wait may not be worth it (and it's far).

Favorite Cafe(s): Intelligentsia (all over), Jumping Bean (Pilsen)

Etc.

In summary: Lots to see here, good easy public transportation, not too expensive. I like it.