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Who is the tricycle knife sharpener? I think he's from OakPark but he takes his mobile workshop to many Chicago neighborhoods once a year.

Asked by Chris Robinson

I keep hearing about all these people who are leaving Chicago despite all this housing being built. Who are they and why are they leaving?

Asked by Jed

Do the skyscrapers in Chicago get their windows washed? Is window washing a relatively safe job? How does one even get into the trade?

Asked by David Lauer

I have read there are four public pay phones in NYC. Are there any remaining public pay phones in the City of Chicago which accept coins?

Asked by Don Meckley

I'd like to hear from people in Chicago who have started businesses, or changed careers later in life. What were their "oh shit" moments and...

Asked by Tina Iglesias

How did the city choose the man who announces stops on the CTA?

Asked by Anonymous

What is it like to live in the city?

Asked by John Fine

Why does Chicago have a glut of mattress stores - often many on the same corner? How is this sustainable? Who's buying all these mattresses?

Asked by Steve Gadlin

Why did people decide to build wooden little free libraries and put them on their lawns?

Asked by Anonymous

Who is the Santa on the CTA holiday train? Is it always the same actor? Is it a CTA worker? I’m really interested in the Santa specifically

Asked by Bee

How are the spiritual and emotional needs of Muslim female service members in the U.S. Military met?

Asked by Saleha Jabeen

Do skyscrapers and other buildings downtown have a master light switch to turn on and off all the lights on all the floors?

Asked by Sean T. Boudreau

With the rise of digital billboard on the highways, how has the job of billboard artist change over the years?

Asked by Anonymous

How do you drive a CTA train?

Asked by Anonymous

What happens to the millions of little toiletry bottles and partial used soaps that are left behind each day in our city's hotels?

Asked by Lisa Greyhill

Every day I see a growing number of homeless on the streets and on trains begging. What options do we Chicagoans have to help?

Asked by Elise Glickman

What does it like to be a snow plower?

Asked by Diane

If I flush a toilet on the top floor of the Sears Tower, how long does it take for the contents to get to a waste treatment facility?

Asked by Fred Weber

I've heard that PR people used to send press releases in pneumatic tubes under the Chicago River to the Tribune. What happened to the tubes?

Asked by Grant Fuller

Why is there always an artificial sweet(ish) almost incense-like smell coming from Union Park?

Asked by Grace

How do you get a job selling ice cream from a rolling cart? And where do you have to go?

Asked by Samuel Osorio

When's the best week this summer to avoid crowds? I'm semi-handicapped and could do without all the conventions, etc. but want to visit

Asked by Walt Jackemuk

How many CHA housing vouchers get used on the Northside and why?

Asked by Anonymous

Why does the Chicago Fire Department have boats, what is their history and what is a typical day for a boat firefighter (if that's a thing)?

Asked by Aisha A

How old are the cribs out in the lake that bring us water, what is their lifespan, what is the upkeep like on the crib and underwater?

Asked by teresa elward

How does the CTA wrap L cars and buses with advertising? Is there a special facility? How long does it take? Who decides what ads get OKed?

Asked by Drew Steele

Is baked mostaccioli a regional dish? Specifically, the kind you'd get at a graduation party with beef, chicken, and salad.

Asked by Conor

"GetyourworldsfinestchocolateHOWYADOINTODAY" Saleslady outside at Madison and Clark *sings* it over and over. What's her background/profit?

Asked by Mary

Who puts those clothing "donation" boxes on the corner of gas station lots, what happens to the clothes, and who benefits?

Asked by Carl Segal

What is the background of the singing World's Finest Chocolate saleswoman outside at Clark & Madison? She's famous in that part of the l...

Asked by Mary

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