[Pahaska]

A jeep with 5500# towing capacity will only tow a very small and/or very old Airstream, when loaded as you describe. A good rule of thumb is to stay below 75% of the rated towing capacity to have reasonable performance. Airstreams tow quite easily, but they are not very lightweight except the very old ones.

You will not find a lot of folks on this forum that advise towing with a jeep because they are high, short wheelbase, and narrow. I would not personally advise the combination of the jeep and a 25' Airstream regardless of what Chrysler says it will tow.