CTAF/UNICOM: 123.0 = Local advisory freq
CHICAGO APPROACH: 133.1 = Air traffic control for arriving aircraft, especially IFR (instrument flight rules).
CHICAGO DEPARTURE: 133.1 = same but for departure.
WX AWOS-3 at GYY (6 nm N): 134.575 (219-944-0010) = automated weather at GYY and phone no.
WX AWOS-3 at IGQ (6 nm W): 119.275 (708-895-9526)
WX ASOS at VPZ (18 nm E): 125.875 (219-531-1770)
COMMUNICATIONS PRVDD BY TERRE HOUTE RADIO ON FREQ 123.65 ( CROWNPOINT RCO).
RCO= Remote Communications Outlet, by using this freq the pilots are talking to controllers stationed at Terre Haute. You should be able to receive this if you're nearby by (10-15 miles). Most if not all RCO's include a radar site so that the controllers can see what's happening in this airspace.
I'm a pilot and I listen to Jacksonville, Fl (Jax Center) on 127.95 through RCO which is 13 miles away using just a rubber duck. In fact the traffic on that freq is non stop. At night the controller handles all the quadrants so I can hear them talking to far off aircraft all over about a 200 mile radius from Jax. I can also hear two way conversations in about a 90 mile range of the local RCO.
Keep in mind that aircraft have the line of sight working for them so you can hear them much easier than a transmission from a ground based unit. Case in point, I live 7 miles from the major airport here but I can't receive any of their transmissions. I can however, hear all of the transmissions from airborne aircraft on both app/dep, twr, and unicom freqs. The flow is this, enroute the plane talks to Jax, then to Chas app, then to Chasn Twr, and finally to Chasn ground control after landing. Each controller clears the plane to a prescribed point and altitude and then passes it to the next controller.
Hope that I haven't confused you too much, just apply it to your area/airports.