Flying into Chicago to get to "The Loop" or downtown is somewhat of an expensive hassle, or had been for me until I discovered Gary, IN (GYY). Rather than going into Midway or Palwaukee and incurring about $50 in fees and 100LL at $8 per gallon in addition to ATC delays I tried using GYY on my last trip. No landing, ramp or parking fees at the FBO I used (B.Coleman)- not sure about Gary Jet Center as I didn't check with them. Fuel less than $5/gal. FBO drives you the mile to the train station and the train to downtown is $6 each way. They also pick you up if you call from a couple stops before the Gary Airport station. There are now 2 FBO's there thus the lower price on fuel and services. Gary Jet Center and B-Coleman Aviation (the new kid on the block). B-Coleman is slightly less costly on fuel and is constructing a new, large facility. In the meantime their temporary facility is quite nice. GYY is not very busy, tower folks are friendly, good approaches, and the train ride is quiet and comfortable. About an hour each way to downtown. MDW is closer to downtown but more of a hassle and with ride by FBO to station and train (often crowded local transit) it is just a little less than an hour. Also can take a taxi from MDW for more $$. Rental car available at GYY or MDW if that is your preference. Train schedule here: http://www.nictd.com