Palwaukee can be a challenge in the windy city when the runway is wet and the "windy" gives you a strong crosswind.
Summer: UTC -5 CDT (Summer)
Winter: UTC -6 CST (Winter)
The only suitable runway is fairly short, there is an ILS to one and and an RNAV(GPS) with LPV minimums to the other, the departure procedure from Runway 16 is aggressive.
The arrival from the east will more than likely be from FIYER to OBK to the ILS.
The arrival from the east will more than likely be from FIYER to OBK to the ILS-16 circle to 34. (As shown in the video: KPWK Rwy 16 Circle Rwy 34 (2013-10-21).)
The circle has more than a few constraints that can bite you if you don't plan properly. You will have to be no higher than 1900 feet MSL because of the KORD Class B overhead which begins at 1900 feet. You will have to keep your base within a bit less than 3 miles to avoid the part of the Class B which starts at the surface. There is a very large landmark, the AON building, about halfway through the base turn:
If you plan your downwind to be just a mile east of the building and then plan to turn right on top of it, you will be able to avoid the Class B and still roll out on final to Runway 34 about 500 feet AGL.
Departing 16 you can expect the Palwaukee Departure, requiring a fairly aggressive turn right after takeoff. You should ask for a turn east instead, you might get it. I've done the procedure and just made it:
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