It’s Always Sunny In... Chicago? In October? #FlytheW Edition | The Odyssey Online
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It’s Always Sunny In... Chicago? In October? #FlytheW Edition

Pumpkin and spice and everything red, white, and blue?

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It’s Always Sunny In... Chicago? In October? #FlytheW Edition
Wikipedia Commons

Pumpkin and spice and everything red, white, and blue? Confusing… yes. Much like Chicago’s weather during the month of October, hitting record-breaking temperatures. (but *cough cough* apparently global warming still isn’t real?). Don’t worry though hoodie season is right here, this week temperatures are supposed to cool down. Meanwhile, though, we can’t even get too shaken up about the offset temperatures when it is the absolute best time of the year in Chicago. That’s right. Baseball playoff season. City go’ers are eating, sleeping, and BREATHING red, white, and blue.

Coming from someone who was fortunate enough to live through last year’s 108th year ending drought, the experience of that entire process is something I’ll talk about at my wedding during my “Oh my gosh I can’t believe how fast the time went,” cliche speech. But that feeling, that rush, and electric city feel, the entire city of Chicago is just yearning for more. Our blood is starting to boil for that feeling again. A time when the city comes together like you’ve never seen anything come together. I mean our city is recorded as being the 7th largest human gathering in history. HISTORY. But that’s not enough for us. We need more. And we’re gonna get it. Fly the W flags fill the streets, buildings, and homes of this eclectic city. Scarecrows are dressed as Cubs players. Kids skipping back to their Lincoln Park apartments after a long day at school are screaming the ‘Go Cubs Go’ lyrics all the way home from the bus stop. This city is literally bleeding red, white, and blue. This past week, the Cubs were able to close out a series with the Washington Nationals, moving on to their next series against the Los Angeles Dodgers this week. Looking to further their playoff time, and eventually getting another chance at a World Series title.

It’s hard to forget during all of the beautiful madness of playoff season, that it’s also (in my opinion) the best and spookiest month of the year. October. Between the magical colors of the leaves changing colors and flooding the city streets, and the smell of pumpkin spice and sweet, delicious apple pie, Chicago has so much to offer during this wonderful time. This city is known to have some of the scariest, and haunted buildings and hotels known to man. (here are some of my favorites, because I do love a good scare).

  1. Congress Plaza Hotel - The Congress Plaza Hotel, located in the heart of Chicago’s loop is known for being Chicago’s famously haunted hotel. It has been known in past years to have the longest employee strike in history, due to its workers never feeling quite safe because of the hotel’s past. The twelfth floor has a room so haunted that his been personally sealed, and locked off. Brides have gone missing from the main piano room during pictures, and guests have sworn they’ve seen a one legged man in the elevator. The Congress Plaza Hotel is open to the public. So… enter if you dare. (At your own risk of course).
  2. Holy Family Church - Holy Family Church, located in Chicago’s Little Italy is known for being one of the main buildings that survived the Chicago Fire. Coming all the way from the late 1850’s, church go’ers swear they see ghosts late at night when closing the church down. At the forefront of the church, bears two statues of boys, each holding a candle over the altar. These two statues are said to be believed that the two statues of the boys that held spirits leading a priest to a woman that was dying, who needed to receive a lasting ritual. Witnesses have also seen several figures standing in the loft of the choir, even after the church had been closed off for years. The Holy Family Church is also open to the public… again, at your own risk of course.
  3. The Drake Hotel - The Drake Hotel, located in Streeterville along Chicago’s Lakeshore Drive, holds one of the most tragic stories to ever be told. Otherwise known as the night that the “Woman in Red,” ended her very own life. It happened on the night of New Year’s eve in 1920. A young woman accompanied by her fiance attended a huge gala located in the hotel’s famous Gold Coast Room. During the middle of the night, the woman lost sight of her fiance, and in return went through the hotel looking for him. Only to find him fooling around with another woman. In agony, the woman climbed to the roof of the hotel and jumped to her death. Guests have reported seeing the ghost of her not only on the top floor of the hotel, but in the Gold Coast Room as well. The Drake Hotel, also open to the public is all yours if you need a good scare. Quite tragically romantic...I would say.

Between the beautiful fall city streets, inescapable Chicago sports spirit, and enough haunted buildings and hotels to fill all of your spookiest needs... Chicago is the place to be this October. So hang your #FlytheW flags high, and keep your heads and spirits even higher. Because it's only just the beginning for The Windy City. And as always never forget... GO CUBS GO.

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This article has not been reviewed by Odyssey HQ and solely reflects the ideas and opinions of the creator.
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