Originally Posted by EmailKid

UA is pretty good about protecting you IF it's from another UA flight on separate reservations. They also have an unpublished "flat tire rule." Of course this may not help if Biz class is sold out for next day.

Now a serious concern, because many travel wit checked luggage. On separate tickets you may be OK if it's UA, as they *should* be able to check through, though there were reports in United forum that it could sometimes be a problem. Of course if it's a different carrier, you would have to leave secure area and pick up and then check the luggage for the next flight and then clear security.

There is also the option of driving to ORD only and flying back to Detroit as domestic OW flights tend to be half of RT (unlike Int'l flights).

I've done these positioning flights several times for good fares, though for me it pretty much always involved an overnight stay - which was OK back in the day when AirBNB did not charge exuberant prices for cleaning in addition to the room fee

And I can tell you that ORD is pretty easy to get around (past security) - at least in the UA area. Not sure about the area where other airlines are located.