Chicago Jokes

  • Funny Jokes

    Chicago Cubs For Sale

    Hot 4 years ago

    It was reported that at the end of the season the Chicago Cubs will be sold.

    Current ownership is looking for anyone willing to piss away $5.

    Transfering to Chicago

    Hot 6 years ago

    A man was telling his co-worker one day that the company was transferring him to Chicago. He explained that he was going to quit before he had to move there.When asked why, he replied that he was just too afraid of all the crime even though he would be passing up a big salary increase and greater benefits.His co-worker said to reconsider and that Chicago was a magnificent city, with world class museums, loaded with a great history, sites, close to Canada, good public transportation, etc.Then he said: "Why I myself worked in Chicago for almost 10 years and in all that time I never ever had a problem with crime while I was working."The first asked, "What did you do there?"To which the other replied, "I was tail-gunner on a bread truck."

    Speedy Flight

    Hot 5 years ago

    Not realizing that Indianapolis is on Eastern Standard Time and Chicago on Central Standard, a blonde inquired at the Indianapolis airport about a flight to Chicago.
    "The next flight to Chicago departs at 1:00 PM," the ticket agent said, "and arrives at 1:01 PM."
    "Would you mind repeating that, please?" asked the blonde.
    The agent repeated the information and then asked, "Would you care to make a reservation, sir?"
    "No, thank you," replied the blonde, "but I do think I'll stick around and watch that thing take off."

    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...

    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...

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