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Chicago's November Weather: A Rollercoaster of Sunshine, Showers, and Crisp Air

  • Nishadil
  • November 05, 2025
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  • 2 minutes read
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Chicago's November Weather: A Rollercoaster of Sunshine, Showers, and Crisp Air

Well, hello there, Chicago! It seems our beloved city is about to put on another one of its classic, unpredictable weather shows. After a delightful — dare I say, almost unseasonably mild — start to November, you might be tempted to keep those light jackets out just a little longer. And for a brief moment, you’d be right!

This past weekend, truly, was a pleasant send-off to what felt like an extended autumn. Saturday, November 4th, began a bit coyly, perhaps with a few sprinkles playing hide-and-seek in the clouds early on. But, and this is the important part, it graciously cleared up, giving us highs well into the 50s. Sunday, then, really rolled out the red carpet; sunny skies and temperatures flirting with the 60-degree mark made it a picture-perfect day. Oh, and yes, don't forget we "fell back" as Daylight Saving Time drew to a close – a little extra morning sleep, perhaps, before the inevitable chill set in.

But alas, as all good things often do, this stretch of autumnal grace is poised to take a distinct turn. As we usher in the new work week, particularly by Monday, November 6th, the forecast has a rather different story to tell. Expect cloudier skies, for one, and a much higher likelihood of rain making a definite appearance. Temperatures, in truth, will begin their more significant descent, struggling to climb much past the mid-40s. So, that lighter jacket? You might want to layer up a bit more, or perhaps reach for a proper coat.

The rest of the week, honestly, settles into a fairly consistent, cooler pattern. Tuesday and Wednesday, November 7th and 8th respectively, look to offer a bit of a reprieve from the persistent rain, granting us partly sunny conditions. But don't be fooled by those peeks of sun; the air will remain crisp, with highs stubbornly staying in the mid to upper 40s. It’s that quintessential Chicago late-autumn chill, the kind that reminds you winter isn't too far off.

Then, as we lean into Thursday, November 9th, and head towards the end of the week, expect more of the same — partly sunny skies, yes, but still quite cool, holding steady in the upper 40s. And just when you thought you might be able to put away the umbrella, Friday, November 10th, looks set to bring back those clouds and, you guessed it, a good chance of more rain, keeping temperatures once again in the mid-40s. So, for once, it’s not entirely a surprise: Chicago's November weather is reminding us who's boss, offering a classic mix of brisk air and refreshing showers after a delightful, yet fleeting, mild spell. Time to embrace the layers, perhaps, and definitely keep that rain gear handy!

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