Great plan! Many great thing to see in Chicago. Don’t forget to schedule a side trip to Minneapolis-St Paul (twice the fun!). Plenty of direct flights to NYC, closer to Grinnell than St Louis, and way cooler place to visit (minus the pretty, giant arch thing!) 
Plus you said youve already been to St L before!!
How did I miss this thread in my obsessive CC searches during the application and waiting process? (Though I do recognize many of the posters from other threads.) S and I heading to Grinnell Sunday. Applied to many of the schools discussed here, and happily ended up with more choices than expected. It’s down to Grinnell, Oberlin, or state flagship. He visited Grinnell last spring with H, and liked it – hoping this visit makes the decision!
One final update here.
Friday was move in day at Grinnell. 10.5 hours door to door with an enormous amount of stuff. We shipped a large duffel ahead of time, which helped. Wound up picking up 11 packages from the mail room. No, the distance is not ideal, but everything else seems to be. Daughter has found all these people she had been taking to on Facebook, plus meet at ny meetups. The reports so far are nothing but positive. She’s meeting so many different people and doing all of the freshman activities. She wound up with an international roommate from South Korea who had lived in the US for many year. Very nice girl. So far all of the reports are glowing.
We turned the long trip into a little vacation by driving to Chicago and staying 2 nights after the drop off.
We are going back in less than a month for family weekend and can’t wait to see what’s going on.
I’m very proud of how our daughter has adapted to this big step. I’m also very proud at how the whole family went about the process. A lot had to go right to wind up here, but i think we did all could to help the odds go in our favor. Everything has worked out perfectly so far. I’m sure there will be some bumps and a homesick call or two, but we all know she wound up in the perfect place.
Again, thanks for everyone’s help and i only can hope this thread helped someone else in some way and that all of your kids wind up in best place for them.
Also, great meeting some of the other Grinnell parents from this forum.
Congratulations on your new vacant room. 
So happy to hear how well it has gone for her. My daughter is equally happy, though a little homesick. I’m sorry I missed the Grinnell meet and greet for CC parents, hope that there may be another one Family Weekend . . .