Jamie, if you don't mind I'm gonna ask you a few questions, offer a few suggestions, and talk about the way I do a few things.
First, what's your approximate age? Next, what's your approximate height and size?
Those will point you to the best suggestions on what to wear for Pinkfest or for about any activity at hand.
Next, what's your skill level regarding hair and makeup? Can you do a basic face? This is usually more of a concern to those new to public exposure than is outfit selection.
If you're a beginner here, I might suggest booking an "Instructional Makeover" with Kelly, Janna, or Rori (all should be on the Big List at
http://www.geekbabe.com/annie/pinkven/) to get you up to speed.
If you have the basics down pat but want some basic to intermediate-level advice, the Bare Minerals shop in Water Tower Place is very TG-friendly and they will spend quite a bit of time with you for a modest purchase. Ditto with the various counters at Macy's on State.
Do you know where you will be staying (local? downtown? burbs? AirBnB? etc.) and will you be driving a vehicle?
This will determine how much walking you'll do and if there will be any other transportation issues.
Personally, I've tried motels in the burbs to save money, older hotels in the city to save a little bit, the "OJ Hotel" (LOL) as a compromise of cost and convenience, and major brand downtown hotels for convenience. I find that I enjoy Pinkfest (and other Chicago trips) best if I spend a little more and get a room at one of the "usual suspect" major chains, which I know will be modern and comfortable. I've learned to kind of hold my nose as I pay the bill at the desk.
(LOL, Ginger's "Junior Executive Suite" at the Red Roof Inn a few years back was the smallest hotel room I ever remember seeing!)
I find I most definitely enjoy Pinkfest best without a vehicle. Parking can be a challenge and I want to be able to enjoy a few adult beverages without risking a DUI summons.
Also, what level of participation do you plan? The full six days? Evenings only or mostly? Daytime?
The reason I'm asking is mainly because I've found it's easy to "OD" on things at Pinkfest (and DLV). I personally try to work in some down time (power nap, etc.) and I also enjoy taking the occasional day off or night off and do my own thing. I'll occasionally do a photo walk day or evening, or do something that the group is not really into.
Anyway, if you can answer the items above, we can more specifically zero in on giving you some suggestions and comments.