Lucky for you, at O’Hare the transportation center allows you to just bring an air mattress and blow it up right there in the airport! Very convenient, I’ve seen some really nice setups with pillows, sheets, blankets, hanging clothes, open suitcases, mini tables… probably coolers and fridges too. Plus you get that community feeling with others to hang out with and talk to.

Win-Win…

Do the hitch-hikers he picks up tell on him to the CHP?

Defintely seen a few sleepers in the employee lots over the years, through it's verboten. You could probably stealth camp by night with a topper or big enough van/SUV, but probably have a plan to be mobile during the day.

Well, this thread went sideways in a hurry. ;) The SWA pilot who converted an old service truck into an off-road RV is talented!

Sounds like my best play is a well-worn crashpad beside the Blue line. Thanks for the replies!

Suggest you find someone looking for a caretaker for their yacht at the marina. Marinas generally have break rooms, with showers, TV ,wifi, and sometimes fitness centers. A buddy did this at Ala Wai for years.

Great way to enjoy the waterfront.
I did this for almost a year in a Chauffeur's quarters at a mansion in Ladue (St. Louis),,while the family was overseas. No waterfront though.