Girl Scout Leader,
First and foremost, I would definitely contact Amtrak and checkout their group rates. You can click
here to be taken to Amtrak’s group reservation form. I would also check out Amtrak’s current 2 for 1 sale. If you go to Amtrak’s website and into the reservations section, enter the code H255 into the promotion code box. This will save a great deal of money, as you will get 2 tickets for every 1 that you pay for. Note: You must buy your tickets before February 15th to take advantage of this special.
Regardless of how you buy your tickets, I would still make sure that you try to make prior arrangements with Amtrak for a group that size. This would probably be easier if you’ve used the group purchase as opposed to the 2 for 1 special that I’ve mentioned. Otherwise, I can promise you that you won’t find the group sitting together, especially on the Cardinal from Cincinnati to Chicago. You might have better luck on the Zephyr out of Chicago, but even then you could get split up. So I highly recommend that you see if Amtrak can make an accommodation for your group by blocking out a bunch of seats.
Now the free meals in the diner, when you travel in a sleeper or first class, does help to mitigate some of the extra cost. However, it doesn’t offset the whole cost of the sleeper. You should also know that only the first person in a room pays for that room. The second traveler only pays railfare, so when you divide the cost of the room between two people it does go down.
If you do go with a sleeper, you may wish to consider only taking the sleeper from Chicago to Glenwood Springs. At the hour you will board in Cincinnati, it's almost not worth paying for the sleeper for that night. Plus they may not even have enough room for your group out of Cincinnati, in the sleeper. I'd ride coach that first night, and treat yourselves the next night out of Chicago.
A few final thoughts: If the kids bring radios or CD players, they must have headphones (unless they are in a bedroom and even then the volume must be kept low). If they bring electronic games to play, they must be able to turn the sound off or again have headphones. Should you decide to travel in coach, I’d still recommend having at least one breakfast in the diner. It’s a nice experience and breakfast is the cheapest meal in the dining car. By the way don't be shocked if the diner can't handle all 28 of you at once.
Last but not least you may want to check out
this page from Prodigy’s On Track On Line website. It is chocked full of hints and tips for train travel.
Please don’t hesitate to come back and ask more questions as they arise.