Originally Posted by bgriff

What is bringing you to Chicago? I don't know how many SPG points you have or what else you might do with them, but if you are there on vacation / tourism, then spending a long ride on the blue line every day really won't be all that fun. It will also make it much harder to run back to the hotel during the day to change clothes, relax for a bit, etc. If you are traveling for work or something (which seems unlikely if using points, but possible) and already know Chicago and don't plan to be doing much in the evenings, then maybe it would be okay to stay out at the airport, but certainly not desirable.

Have you checked for cash & points availability at any of the more centrally located properties? If you are short on SPG points, that could be a good deal. It also somewhat eases the pain of missing out on the 5th night free (since 5th night free is not offered on cash & points rates).

Up to you but if your Starpoints balance is low, going for C&P could be a better deal than going to the Sheraton just for the club lounge access. The club lounge won't be anything too amazing (and there is plenty of great food to eat outside the hotel in Chicago) so don't choose a central Chicago property on that basis alone.

The Tremont is a bit cheaper at 10,000 points per night in a central location though it gets mixed reviews. I haven't stayed there myself but frankly based on everything I've read if you were going to do that you probably might as well go for one of the nicer properties at 12K per night at that point.