City in the midwest also known to claim deep dish as their own, except in a SQUARE shape.
Detroit
The history of Chicago's Windy City nickname is dotted with controversy, but the first repeated effort to label Chicago with this nickname comes from an 1870s rivalry with what other Midwestern city that starts with a C?
Cincinatti
If you had been to Game 3 of the 1932 World Series at Wrigley Field, you would have seen this famous baseball player make a gesture that would go down as one of the most timeless sports moments of all time. Who is he?
Babe Ruth, famous for "Calling His Shot"
What notorious gangster was gunned down at the Biograph Theater?
Al Capone
Also known as "The Chairman of the Board," who sang that Chicago was his "kind of town?"
Frank Sinatra
A lot of the reason for deep dish's popularity came from necessity - from what impoverishing world conflict in history does Chicago credit the reason for such a high-in-calorie, pie-like form of pizza?
World War II!
With a lack of ingredients around for the working class, this was an easy alternative as a cook-what-you-have-and-a-lot-of-it food.
Within 4 percent, what percent of the total population of Illinois lives in Chicago?
21%
17% - 25% acceptable range
The Chicago Bulls are named after this place, famous for being the engine of the renowned Chicago meatpacking industry.
Chicago Union Stockyards
There are 40 restaurants and chefs who have won the ___ ____ award in Chicago for outstanding work in the restaurant industry. Who is the award named after?
James Beard
'Chicago Freestyle' by Drake features another silky smooth R&B vocalist, notorious for the "2:30 baby won't you meet me by The Bean" sample?
What was the first restaurant in Chicago to serve deep dish pizza?
Pizzeria Uno, 1943
Named after a French priest from the 17th century, what Chicago university claims to be the largest Catholic university in the United States?
DePaul
The Chicago Blackhawks most recently won the Stanley Cup in 2015, defeating what Eastern Conference team in the finals?
The Tampa Bay Lightning
Initials J.P. met his comedy partner at Second City In Chicago in 2002. They eventually used their last names as the title for a sketch series that rose to fame. What are the initials of his partner?
"Jesus Just Left Chicago" is a track from the 1973 album "Tres Hombres" by what American rock band that comes at the end of the alphabet?
ZZ Top
Lou Malnati's has establishments in Illinois, Wisconsin, Indiana, and one other state, home to many expat Chicagoans. What is it?
Arizona!
The name "Chicago" is derived from a French rendering of the Native American word Shikaakwa, which is what type of food?
Onion
Mike Ditka played what position for the Chicago Bears?
Tight end
Who technically invented the skyscraper after designing the Home Insurance Building in 1884-85?
William Le Baron Jenney
Lonnie Rashid Lynn, Jr was born in Chicago's Hyde Park neighborhood to a former professional basketball player and educator. After almost a dozen years in the music industry, he earned his first (of many) acting credits in 2003, appearing on the sitcom "Girlfriends." What one-word moniker is he better known by?
Common
One of the most talked about food deals in town is a $7.95 individual pizza lunch special from this pizzeria on N Clybourn with a cult-like following.
Pequod's
The Red Line is Chicago's busiest 'L' rail every day. What is the busiest STOP in terms of foot traffic?
95/Dan Ryan
How long was the Chicago Cubs' World Series drought before they won in 2016?
108 years
The 1909 Plan of Chicago recommended new and widened streets, parks, new railroad and harbor facilities, civic buildings, and much more. The document had a massive influence on the field of city planning. One of the co-authors lent his name to the Plan. What was this man's surname?
Burnham
What founding member of the band Chicago left the group in the 1980s to pursue a solo career, scoring a number-one hit on his own with "Glory of Love," the theme from "The Karate Kid?"
Peter Cetera (good luck getting this one Gavin)