Scanner/Airplanes Question

Hi.

I ran a bunch of searches but all I keep getting is a bunch of discussions
about taking a scanner onboard a plane.

What I am trying to figure out is what the sequence is for airplane
frequencies. I am near both MKE and MWC.

So, a plane wants to take off from MWC (Timmerman).
They contact clearance (same as the ground frequency) to get the OK or the
changes in the route they need to take.

1. They contact ground and are told to move into position.

2. They contact the tower and are cleared for takeoff.

3. The tower then hands them off to ???? Is that "Milwaukee Departure?"

4. Once they are handed off to that frequency from #3 above, I suppose it
depends on the destination as to the next step. Where does "Milwaukee
Departure" end on the map, the first purple circle, the purple circle with
the gradient, or the next (big) purple circle? There are some areas that
are not included in any of the purple circles. Does this mean the plane
does not talk to any controller while in that area?

5. If the plane was, instead, a regular passenger plane (as in, "We're
flying to Florida to visit grandpa") taking off from MKE, what would the
steps be (on the radio)? Would it be the same as above except they would
switch from "Milwaukee Departure" to one of the Low/High/Ultra High
frequencies? Is that all printed on the Low/High charts?

Basically what I am looking for is to "follow" a plane on the radio, not
any specific, exact location but from one frequency to the next.

Thanks in advance.

P. S. Delete the necessary part of my e-mail address if you want to
respond directly.

The typical sequence at a large airport is:

1) listen to ATIS frequency... note pertinent info.
2) contact clearance delivery with ATIS code... get clearance and Departure freq.
3) contact ground get taxi clearance
4) contact tower when ready to go for TO clearance
5) on climbout tower has you contact departure in freq assigned by (2)
6) departure hands you off to center (if IFR or sometimes VFR with FF)

This sequence would be the same for all aircraft departing.