The 2nd zone for that award really bumps up the amount of points needed (30,000), so I guess we either pay the difference from TOL to say Chicago, or else we just plan a trip further out and get our "points worth" - like Denver or somewhere out on the edge of zone ll.
If you're heading East you can go to basically anywhere between Ohio and Florida, the longest trip East to Toledo would be to Miami....
In any event going East what you need to do is redeem a reward from TOL- your destination. Most likely your room won't be sold between CHI-TOL so you can then call the regular Amtrak ticket agent, explain what is going on, and book the exact same room you're given by the AGR agent. This means you don't have to switch rooms mid-trip and you also get to earn AGR points for that ticket.
This principle works going West too. Redeem TOL-CHI and wherever in the Central zone you wanted to go-- after you get your assigned room TOL-CHI get transferred to a regular booking agent, tell them what car/room AGR put you in TOL-CHI and book it from WAS-TOL.
However it may be better to buy the WAS-TOL segment first and redeem the AGR award next. This is because it is more likely that somebody will purchase the same room WAS-TOL than TOL-CHI, so you run the risk of getting sold out. If all ten bedrooms on the CL are booked between WAS-TOL, you won't be able to purchase one for that segment.
(There's probably a sparknotes version of this somewhere).
If you're going West you can then go to any number of places on the same reward. Remember that your reward stays the same even if you transfer trains. By redeeming a bedroom you'll have bedrooms the entire way (or BC seating on non-sleeper trains). You could head to NOL, DEN, Texas, ect. Anywhere in the Central region.
If you knew where you were starting and where you were planning on going, this would be a lot easier to tailor to your individual needs.
