I was also going to recommend the Airport Hilton. It’s just so convenient, and since I’m mainly an American Airlines person I’ve been stuck overnight in Chicago more than once.
I didn’t note whether you said you’re flying American, but just note that the Admiral’s Club will ONLY be available to you if you’re flying American or one of its code share partners.
Tried to get her to join me in LaCrosse this summer; the only flight had a 35 min connection in ORD. Why do they even offer nearly impossible connections like that?
I’m a photographer & I do a lot of night photography. I did read an article about someone who got stuck there overnight about how the terminals were both nearly empty & relatively dark as they apparently turn out a good percentage of the lights. I haven’t done it but I want to book a flight so that I get ‘stuck’ there overnight just for the photo op. Tripod & long exposure to compensate for the low light so if there is someone walking they appear ghostlike. Oooooh, a haunted airport!
Or fly in to (or out of) Rochester, which is only 70 miles from La Crosse. I don’t kbow what time you need to be at O’Hare, but AA has a few flights throughout the day, mainly serving Mayo Clinic patients and staff.