Orlando Jokes / Recent Jokes

On the WBAM FM morning show in Chicago, the DJs play a game where they award winners great prizes. The game is called "Mate Match." The DJs call someone at work and ask if they are married or seriously involved with someone. If the contestant answers yes, he or she is then asked 3 random yet highly personal questions.

The person is also asked to divulge the name of their partner (with phone number) for verification. If their partner answers those same three questions correctly, they both win the prize.

One particular game, however, several months ago made the City of Big Shoulders drop to its knees with laughter and is possibly the funniest thing I've heard yet. Anyway, here's how it all went down:

DJ: "Hey! This is Edgar on WBAM. Have you ever heard of' Mate Match'?"

Contestant: (laughing) "Yes I have."

DJ: "Great! Then you know we're giving away a trip to Orlando,Florida if you win. What is more...

The following are actual stories provided by travel agents:
I had someone ask for an aisle seat so that their hair wouldn't get messed up by being near the window.
I got a call from a woman who wanted to go to Capetown. I started to explain the length of the flight and the passport information then she interrupted me with, "I'm not trying to make you look stupid, but Capetown is in Massachusetts." Without trying to make her look like the stupid one, I calmly explained, "Capecod is in Massachusetts, Capetown is in Africa." Her response... click.
A man called, furious about a Florida package we did. I asked what was wrong with the vacation in Orlando. He said he was expecting an ocean-view room. I tried to explain that is not possible, since Orlando is in the middle of the state. He replied, "Don't lie to me. I looked on the map, and Florida is a very thin state."
I got a call from a man who asked, "Is it possible to see England from more...

The following are actual stories provided by travel agents

I had someone ask for an aisle seat so that their hair wouldn't get
messed up by being near the window.
A client called in inquiring about a package to Hawaii. After going
over all the cost info, she asked, "Would it be cheaper to fly to
California and then take the train to Hawaii?"
I got a call from a woman who wanted to go to Capetown. I started to
explain the length of the flight and the passport information when she
interrupted me with "I'm not trying to make you look stupid, but Cape
Town is in Massachusetts." Without trying to make her look like the
stupid one, I calmly explained, "Cape Cod is in Massachusetts, Capetown
is in Africa." Her response... click.
A man called, furious about a Florida package we did. I asked what was
wrong with the vacation in Orlando. He said he was expecting an
ocean-view room. I tried more...

A man called, furious about a Florida package we did. I asked what was wrong with the vacation in Orlando. He said he was expecting an ocean-view room. I tried to explain that is not possible since Orlando is in the middle of the state. He replied "Don't lie to me. I looked on the map and Florida is a very thin state."

Here is some funny, and supposedly true stories from travel agents.

I had someone who wanted to stay at the Bob Newhart Inn in Connecticut. When I explained that the inn was fictional, the customer became very irate and insisted "I know it is real, I see people check in every week!"

Also, I really did have someone ask for an aisle seat on an airplane so their hair wouldn't get messed up by being near the window.

A client called in inquiring about a package to Hawaii. After going over all the cost info, she asked, "would it be cheaper to fly to California and then take the train to Hawaii?"

I got a call from a woman who wanted to go to Capetown. I started to explain the length of the flight and the passport information when she interrupted me with "I'm not trying to make you look stupid, but Capetown is in Massachusetts." Without trying to make her look like the stupid one, I calmly explained, "Cape Cod is more...