I've been trying to ask my personal circle of friends but no avail.

I am leaving on Monday from O'Hare for my one month trip to Jordan, Israel, and Southeast Asia.  

1. I'm flying from Chicago to Amman, Jordan and getting issued a single entry tourist visa upon arrival.
    Time in Amman: 5 days
2. I'm then traveling by land from Amman, Jordan to Tel Aviv, Israel where I don't need a visa.  
    Time in Tel Aviv: 4 days

*3. This is the trickiest part and I've read about a lot of horror stories and people being denied entry. On my travel by land back from Tel Aviv to Amman, this is where is the issue gets tricky.  

    Time in Amman: 2 days until my outbound flight to Southeast Asia

From Israel to Jordan, I am allowed to use the same single entry visa that I receive from the Amman airport. The conditions include making sure that the visa was granted fairly recently (I think within past 30 days) and that I only use the King Hussein/Allenby bridge. That is the technically the rule but I'm worried about still being barred because I've heard nothing but bad things about Jordanian immigration officials.  

For those who have experienced thus travel, what do you recommend? Should I just apply for a multiple entry visa from the Jordanian Embassy in Tel Aviv (as no visas can be issued at border crossings)? Should I just not worry about it

I have had similar issues in other contentious parts of the world.  Although I have never been there, I highly recommend a multiple entry visa.  I would also try to get it before I leave the US.  Embassy's in other countries are not near as efficient (tend to operate on island time, if you know what I mean.)  Sounds like a great trip, have fun and stay safe

Having traveled in the middle east and in Africa, I would suggest leaving nothing to chance. I echo what was previously stated. This is a different part of the world and you want to make sure that everything is in order.
 Even if everything is in order, there can be problems, they are trying to shake you down for dash (bribe as it is known in Africa).  
There are lots of things to do and see in Jordan and Israel, it will be a great trip, but leave nothing to chance.

You should leave nothing to chance, it is hard to predict what will happen at the Jordanian/Israel border. Expect to be interrogated on your travels in Jordan, who you saw, who you were with. Israel (for many good reasons) is extremely cautious about who enters the country and can delay you no matter what visas or other paperwork you might have. I have traveled to Israel on more than one occasion and have experienced trying to enter from Jordan. It is doable, just be patient and respectful.

You should go downtown and get a 2nd passport. If you had asked early enough I would have recommended one of another country if applicable.

I just made this crossing (both ways) recently. If my experience and the experience of many of my friends who did the same is any indicator, it was pretty easy. I would not anticipate any problems. If you'd like to troubleshoot potential issues or if you have any questions, please feel free to email or chat me, though!  Are you flying Royal Jordanian from O'Hare? It's non-stop!

Could you fly from Israel to Jordan and avoid the border?

Thank you. This has been very helpful! I will definitely PM you. The six legs of transport makes it feel like I'm on the Amazing Race!

Yes I am flying Royal Jordanian nonstop to Amman. -- Modified on 11/2/2013 11:17:31 PM

I'm leaving on Monday night and it's too late for me to apply for a multiple-entry visa. Traveling by air would definitely require a multiple entry visa to go back into Jordan.