Chicago Bob
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History! Trivia! Hilarity!
08/15/2026
📚 MEET THE AUTHOR this Sunday!
I’ll be signing A Century of Hilarity at The Book Loft’s Local Author Takeover in Oak Park.🗓️
Sunday, August 16
⏰ 11 AM – 1 PM
📍 1047 Lake Street, Oak Park
Come say hi, grab a signed copy, and let’s talk the real (and hilarious) Chicago. Free to attend!
See you there 👋
BookSigning LocalAuthor WindyCity IndieBookstore ChicagoAuthor
CTA priority seating announcement just got an update 😆
“Priority seating is intended for the elderly, passengers with disabilities, and people who voted for Brandon Johnson.”
Just me looking bored on the actual Chicago ‘L’ while the voice stays honest.
Agree or disagree? 👇
08/11/2026
Get you signed copy this Sunday!
08/09/2026
Family day on the Comical History Tour along the Chicago Riverwalk.
Loved sharing the stories, the skyline, and a few laughs with my favorite people.
Private or group tours available — DM me or check the link in bio.
08/06/2026
Shrog the cat is not impressed with Chicago’s jibarito… he calls it a gross banana taco 🍌Until the bananas fight back.
In this short animated skit, Chicago Bob tells the real story of how the jibarito was born in 1996 at Borinquen Restaurant in Humboldt Park. Juan Figueroa ran out of bread, smashed twice-fried plantains instead, and accidentally created one of Chicago’s most beloved sandwiches.
Puerto Rican pride in plantain form — pure Chicago food history with a side of chaos.
Have you tried a jibarito? And be honest… Italian beef or jibarito?
Drop your answer in the comments 👇
Chicago's Jibarito: Not a Taco, Not a Banana Disaster! 😱 🍌 Link to My new book! https://a.co/d/0j82ZMHKShrog the cat thinks C...
I think the CTA announcement needs to be updated 😂
“Please be considerate when listening to the Beastie Boys in your boom box…
so as not to disturb other homeboys.”
Just me looking bored on the actual Chicago ‘L’ while the voice stays stuck in the ‘80s.
What year should this be from? 👇
NBC Tower Chicago looks fancy…
…but let’s be real 😂
Built in 1989 by the same architect who later designed Trump Tower.
It’s “Echo Deco” architecture — basically Art Deco revival trying to look like 30 Rockefeller Plaza in New York (home of SNL, The Tonight Show, Late Night…).
Except no iconic late-night shows were ever made here.
The closest this building got?
The Jerry Springer Show.
Jerry! Jerry! Jerry!
Chicago Bob dropping the real history.
Would you rather watch SNL or Springer in this building? 👇
Always Trust Your First Instinct… Except When Plugging In a USB 🔌
Always trust your first instinct…
…except when plugging in a USB.
Then trust your third instinct.
The universal struggle, finally explained with wisdom.
07/30/2026
The Chicago Theatre has the most photographed marquee in the entire city. 📸
That giant red “CHICAGO” sign stops people mid-sidewalk, creates human pile-ups, nearly causes avalanches on the ‘L’ stairs, and maxes out phone storage with endless nearly-identical photos.
It opened in 1921 as a lavish $4 million movie palace during the golden age of silent films and vaudeville. After nearly being demolished in the 1970s, it was saved and reopened in 1986 with Frank Sinatra headlining the comeback.
Today it’s still pure Chicago glitz — and the ultimate “I was here” photo spot.
What’s your favorite landmark to photograph in Chicago? Drop it in the comments below! 👇
The Iconic Chicago Theatre Sign: Why Everyone Stops (and Almost Causes Chaos!) in Downtown Chicago Link to My new book! https://a.co/d/0j82ZMHKChicago is photogenic ...
The CTA train voice said what a lot of people are thinking 😆
“Anyone who attacks a CTA worker or customer can face up to 10 years in prison…
but will probably face zero years because laws aren’t enforced in Chicago.”Just me looking bored on the actual ‘L’ while the announcement hits different.
Agree or disagree? 👇
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