Windy City @ChicagoObserver
Observations from the great City of Chicago Chicago, IL Joined November 2012-
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Windy City retweeted
Day off vibes. 😌 Happy Labor Day, Chicago! 📸: waywelling via IG #NeverOutdoneChi
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Windy City retweeted
Love ya, Chicago.
Windy City retweeted
“Being able to put on that uniform as a home player … it’s just the most special thing you’ll ever do.” Kyle Hendricks loved playing at Wrigley as a Cub 💙
Windy City retweeted
It is a brutally pretty city. And I DON’T CARE if those are actually Bauhaus style! That joke doesn’t work architecture nerds!
Windy City retweeted
Life's a Beach at Oak Street in Chicago. August in the Windy City.
Windy City retweeted
When you sweep a doubleheader, you fly two W flags.
Windy City retweeted
Justin Turner’s pinch-hit walk-off home run is the first by a Cub since David Bote in 2018 🤯
Windy City retweeted
In a recent article for The Atlantic, David Brooks relayed a wonderful story about the devotion that Chicago Cubs legend Ryne Sandberg had for baseball. Sandberg was a phenomenal player and a truly decent person. RIP, Ryno.
Windy City retweeted
In Wrigleyville this weekend there were kids holding a lemonade stand to raise $ so one of them could get their hair done like PCA (bleached with blue stars). #Cubs PCA heard about it and showed up to meet the kids & give them enough $ to get the hairdo 🥹
Windy City retweeted
Rest in peace to Ozzy Osbourne Your 7th inning stretch at Wrigley will never be forgotten
Windy City retweeted
Windy City retweeted
Paul Konerko got a special signed Pope Leo XIV jersey to kick off the 2005 World Series celebration
Barry Butler captures Chicago like few others 👏
Barry Butler captures Chicago like few others 👏
Windy City retweeted
This is some pretty cool research by @zillow about home price affordability and median incomes in different cities. Chicago is the only city in the top 10 where a median income can afford a median home. This confirms what we know: Chicago is THE major city to live in if you…
Windy City retweeted
Windy City retweeted
An incredible debt of gratitude to Officer Krystal Rivera - only 36 years old and a mother to a young daughter. She dedicated her life every day to protecting our city and served bravely until the end of her watch on 6/5/2025. My deepest condolences to her family and partner.…
Windy City retweeted
On this day in 1985, Ferris Bueller took the day off.
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