Help Caitlin with her own Amazing Race Episode!

A plea from Caitlin, a six time race pool player, who recently begun a new job that requires her to do some travel planning. She will be going to Chicago for a conference and needs a bit of assistance on the planning side.

She'll offer a case of beer for the first person to make sense and give a good travel plan. I'll throw bonus points your way. And here's the scenario:

Plane into Midway or O'Hare? Must find hotel for under $200 close to
the El. Rent a car. Find parking for the car. Stay in the suburbs?
(No way.) Is Lincoln Park technically a ring suburb or a
neighborhood? How to see friends and get drunk with them while
working early the next morning? Okay ... get up at 5 to beat traffic
to college fair at Navy Pier ... or catch the El? El to Adlai
Stevenson High School... where's the train schedule? How much would a
cab cost? What's faster? Shoot, high school visits only at noon.
Okay ... El to Benito Juarez High School ... how far is that from the
El stop? Is that the school in the scary neighborhood or the one near
Boystown? Is it off Halsted? How far out is Hyde Park? Deerfield?
How did those admitted kids test last year? Can I overnight 400 road
pieces to Navy Pier? Or carry them on the El? Crap. How to get out
of the city and to Milwaukee and back in two days? Crap crap crap.
Oh, and I'm gonna need a martini at the top of the Hancock Tower,
because otherwise why go to Chicago? I can expense the martini,
right? All three of them?

Have fun.