29 Funny Conversations From The ‘Overheard In Chicago’ IG Account


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We love Chicago! The windy city is a great place to live, or at least to spend a week admiring this amazing part of the USA. There are countless things to praise about it, but the best part is surely the quality of living that comes from the people around you. There are many things we could say to describe locals, but the conversations overheard in Chicago that we listed below are a better way to do it, as they speak for themselves. All of them come from a brilliant Instagram account. You can read more in Instagram.

1. The situation 

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Well, we are not sure about this, but we do believe that such witty things can be heard in every part of the city! It is an amazing way to show how amusing this account is.

2. The reaction 

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Now, this is what we call an open-minded person, and we need to admit that only a few people would react in such a manner. It is a brilliant way to get even.

3. The saying 

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Sure enough, not all people would require you to tell them you love them often, but some insist on it. Still, it is better to show it, as actions speak louder than words.

4. The fireworks 

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This is sarcasm at its finest, and we guess that some people would not get it at first and would probably assume something different. Such “games” are typical of other places, too.

5. The temperature 

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Here is yet another post that is witty and describes a situation in the best possible way. We believe that this is the most accurate comparison we have seen lately.

6. The couples 

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This is not something that could be easily discussed in a single sentence, but we still believe that this is an honest opinion based on facts that we agree with.

7. The boyfriend 

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We can all hear this conversation, probably, as the reason for the situation described here is obvious. This person’s boyfriend did not handle the sarcastic question well.

8. The work 

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This is yet another funny conversation that we loved a lot. It is an awesome way to describe how a highway is constantly under repair that motorists struggle with.

9. The turkey 

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Now, this is one way to celebrate the holiday, and we think that it should be turned into a tradition. This would be a hilarious topic on social media, we believe.

10. The club 

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Wow, this is one way to show that some people take adulting seriously, and we are sad to agree with this post. We cannot endure all-night parties anymore.

11. The bartender 

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Here is yet another witty line that most of us could agree with. We have seen this happen a lot, and we can confirm it could be utterly annoying.

12. The weather 

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Yes, this is correct. Those who are not entirely acquainted with the weather in Chicago would probably despise it, but we liked this comparison anyhow.

13. The girl 

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Now, this is probably the scenario we have all seen at least a dozen times. Girls who say this line usually do not have a valid ID to enter.

14. The scooters 

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Well, this is a problem that most big cities across the world have, and we understand that something needs to be done to ensure a quick transit. Scooters would hardly do the trick.

15. The date 

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People need to understand that dating is not what it used to be. You can see how deceiving a person could be, and we would never be able to accept this is their behavior sometimes.

16. The tornado 

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We are not entirely sure if this is a joke, a real situation that happened to this person, or a hypothetical scenario worthy of a movie, but, either way, it sounds funny.

17. The snow 

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Here is how one person decided to be cheeky while explaining why snow melted this fast. We guess that such an example is quite relevant for some people.

18. The camera 

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Seeing how this line turned out to be, we need to admit that it made us chuckle at first, but we thought about the times we looked at the camera and felt intimidated.

19. The weather 

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Here’s yet one more post about Chicago’s unpredictable weather, and you can see that it is a bit exaggerated, but we understand the reasons behind it.

20. The night 

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Now, this is the kind of thing that we would really love to have printed out to give to someone who lives in Chicago and knows all of it is true.

21. The day 

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We see nothing wrong with this post, and we can even relate to it. We guess that even if it was meant to be a funny sentence, it is still a fairly accurate one as well.

22. The country 

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Now, this is something that only locals would understand, and it has a lot to do with their preferences about food, particularly one famous local restaurant.

23. The boat

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Here is yet another very accurate sentence that we guess is true not only for the life in Chicago as we know it, but for other parts of the country as well.

24. The woman 

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Wow, this is one episode that we imagined, and we need to say it is a brilliant one. It is worthy of featuring in a comedy show somewhere, and it would be a success for sure!

25. The delivery 

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Here is a post that some people would think is too exaggerated, but we are convinced that some delays surely neared a few weeks or even a month.

26. The ladies 

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Wow, this is one of the posts on the list that could serve as a dating advice and a red flag at the same time. We know how this works, and the post is correct.

27. The spot 

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This is something very specific, and we guess that such a comment must have been provoked by something in particular that we would never know.

28. The posts 

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Well, there are many things in people’s lives they are proud of, and we guess that a sandwich should not be on top of that list, even if it is from Portillo’s.

29. The group 

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This post is more than enough to make us call our friends and go for a really long trip to Chicago because the described actions sound like a whole lot of fun.


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Patrick Bennet
I love reading and writing. I am a full time student and I study Philosophy in Oxford.

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