The Greatest City in the USA
American Animals
The American Language
America's Northern Neighbor
US Territories
100
A US state whose largest city is Chicago
What is Illinois?
100
An American mammal famous for stealing garbage and washing its food in water
What is a raccoon? 
100
A sound which is pronounced in every position in most American accents, but dropped at the end of words or before a consonant in most British accents
What is the "r" sound?
100
The country which borders the United States to the North
What is Canada?
100
The most populous US territory, located on an island in the Caribbean Sea
What is Puerto Rico?
200
The river that runs through the city of Chicago (don't overthink it)
What is the Chicago River?
200
A canine predator similar to a wolf (but smaller), which often lives in cities
What is a coyote?
200
In certain dialects from the American South, all sweetened, carbonated beverages (sodas) are referred to using the name of this specific, famous soda
What is Coke?
200
Candidates for Canadian Prime Minister are required to know how to speak this language in addition to English
What is French?
200
An important democratic right which residents of US territories do not have
What is voting in presidential elections?
300
A former president of the United States who lived in Chicago's south side and represented Illinois in the US senate prior to taking office
Who is Barack Obama?
300
A large, brown-haired, furry bovine species which once lived in enormous numbers on the American great plains
What is the American Bison?
300
The Pittsburgh version of "y'all"
What is "yinz"?
300
A tree whose leaf appears on the Canadian flag, and whose sap is often poured over pancakes or waffles
What is a maple tree?
300
The US Territory of the Northern Mariana Islands (located in the Western Pacific Ocean) were captured by the US military from this empire in 1944
What is Japan?
400
A distinctive sandwich from the city of Chicago, consisting of roast beef and pickled peppers (giardiniera) on a bun, dunked in beef broth
What is Italian Beef?
400
The North American continent's only marsupial, a small creature with a naked, rat-like tail, which often carries its young on its back
What is an opossum?
400
A dialect of American English which is non-rhotic (doesn't pronounce all of its 'r' sounds) (there are a few of these; just name one)
What is a Boston accent? (Or AAVE, the New York accent, the Transatlantic accent, etc.)
400
Canada's largest city (population approx. 2.8 million)
What is Toronto?
400
The last two states to be admitted to the Union (both in 1959)
What are Alaska and Hawaii?
500
A US department store chain (now defunct) which once owned the tallest building in Chicago
What was Sears?
500
What opossums do when faced with a threat (and the origin of the American phrase "playing possum")
What is pretending to be dead?
500
A distinctive name for a drinking fountain used in parts of Wisconsin
What is a bubbler?
500
A political party in Algeria, whose name inspired a 60s-era militant, left-wing Quebecois separatist terrorist group to call itself the FLQ (Front de libération du Québec)
What is the FLN?
500
A country which was colonized first by Spain, then by the United States, before being conquered by Japan during World War II and finally granted independence in 1946
What is the Philippines?