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What's the better time to visit Chicago: end of May or early August?

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Keep in mind Chicago has like a week of high humidity every summer. It never occurs in May :)

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This year, August. More vaccinations, more people comfortable going out, and the city should be 100% opened (meaning no government closings or capacity restrictions) in June.

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Either one- but hopefully more things will be open in August 🤞🏼🤞🏼

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I would say fall (mid-Sep thru mid-Oct) - but this year august.

May can be a toss up with colder weather. August will be hot. It all depends what you want to do.

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