For a trip that long from Chicago, I would probably fly and rent a car unless the RV drive itself is part of the vacation for you.
Big Bend is huge, so having a normal vehicle once you are there makes things much easier. I would not want to move a 32 foot Class C every time I wanted to explore a different part of the park. If you do take the RV, having a separate vehicle would be high on my list.
I would also look at El Paso as an airport option. No matter where you fly into, you are still going to have a decent drive, but I would compare the total rental cost and driving time before settling on San Antonio, Albuquerque or Tucson.
As for a Jeep, I would only pay extra for one if you already know you want to drive some of the rougher roads. For most of the main sights a regular rental car or SUV should be enough.
Big Bend is one of those places where the distances surprise people, so I would spend more time planning where you stay than worrying about having the perfect vehicle. A decent route and the right base can save you far more hassle than extra gear. I think about online platforms the same way. With Tropical Casino
https://tropical-casino.com/ I would rather know where the slots, live tables, promos and account settings are before jumping around at random. Good navigation matters more than having every possible feature. Plan the route first and the rest usually gets easier.