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Chicago is about 400 miles/6 hours away by car. Only about 45 minutes by plane. We will fly. It will be the three of us meeting about 10 people in Chicago.
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So pretty quick flight
. Have you met those 10 people before?
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I can see why that would be easier.
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Especially considering the different accents and all of that
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I hear you and completely understand. 
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How do you deal in such cases when you know that something will happen and you want to prevent it?
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1 AM and have some insomnia. Although, maybe it's because I got more sleep than usual last night. Hope I get tired soon, though.
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Ah this sucks
. I hope that you will fall asleep quick!