Roadways
Public Transportation
Architecture
Arts and Entertainment
Food
100

This is the name of Interstate I-55

What is the Stevenson Expressway

100

This is the number of rapid transit lines that make up the “EL”

A. 6

B. 7

C. 8

D. 10

C, What is 8. The eight lines span 224 miles and serve an average of 620,000 people per workday, in the pre-COVID era.

100

Which building is famous for having survived the Great Chicago Fire of 1871?

What is The Water Tower.  Along with the pumping station across the street, The Water Tower, built in 1869 out of large limestone blocks, was the only building in the area to survive the fire.

100

What is the proper name of the iconic Anish Kapoor sculpture in Millennium Park?

A. The Bean

B. The Pritzker

C. Cloud Gate

D. Crown Fountain

C, What is Cloud Gate.  Made entirely of stainless steel, it stands 33 feet high and 66 feet long, weighing 110 tons.

100

When a Chicagoan wants to purchase a carbonated beverage, what term do they use to describe it?

A. Pop

B. Soda

C. Soda pop

D. Coke

E. Cola

A, What is Pop.  Pop is most common throughout the Midwest and the Pacific NW.  Soda is used most commonly on the East and West coasts, as well as in St Louis and Milwaukee.  Coke and Cola are used generically to refer to any type of soft drink in the Southern US.    

200

This is the name of Interstate I-290

What is the Eisenhower Expressway

200

Which of these is not an EL line:

A. Green

B. Orange

C. Gray

D. Pink

E. Yellow

C, What is Gray.  The oldest structure remaining on the EL lines is the Garfield station on the Green line, which dates to 1892.  It was part of the line that connected downtown with the 1893 World’s Columbian Exposition.

200

The Merchandise Mart is so big it used to have its own:

A. Hotel

B. Zipcode

C. Moon

D. Marshall Field's 

What is B, Zipcode.  It spans two city blocks and houses 4 million square feet of space.  It had its own zipcode until 2008. It also has it’s own train station.

200

Which of these famous works is in permanent collection of the Art Institute of Chicago?

A. Nighthawks, Edward Hopper

B. American Gothic, Grant Wood

C. Water Lilies, Claude Monet

D. All of the above

D, What is All of the above.  There are 250+ paintings in the Water Lilies series.

200

Which classic American snack food was first invented in the Chicago area?

A. Ho-Hos

B. Oreos

C. Twinkies

D. Cracker Jack

C, What are Twinkies, invented in River Forest, IL.  Despite urban legends of an infinite shelf life, they actually have a shelf life of 45 days.

300

This is the name of Interstate I-355

What is the Ronald Reagan Memorial Tollway

300

In 1993, the CTA unveiled new designations that used color coded signage rather than street names.  Which of these was not the former name of an elevated line?

A. Howard

B. Evanston Line

C. Ravenswood

D. Southwest Route

D, What is the Southwest Route. The Orange Line was referred to as the Southwest Route only during planning.  The Orange Line was the first EL line to be opened with just a color coded name.

300

Which Chicago museum’s building was built for the World’s Columbian Exposition in 1893?

A. Art Institute of Chicago

B. Field Museum of Natural History

C. Museum of Science and Industry

D. All of the Above

C, What is the Museum of Science and Industry.  The building was originally constructed as the Palace of Fine Arts for the 1893 World’s Fair.

300

Which of these bands did NOT get their start in the Chicago area?

A. Earth, Wind & Fire

B. The Smashing Pumpkins

C. Fall Out Boy

D. Chicago

E. Pearl Jam

E, Who is Pearl Jam.  Lead singer Eddie Vedder was born in Evanston, but the band was formed in Seattle. Fall Out Boy is from Wilmette.

300

How many toppings go on a standard Chicago style hot dog?

A. 5

B. 7

C. 10

D. 12

C, What is 7:  Yellow mustard, Neon green relish, chopped onions, tomato wedges, pickle spear, sport peppers, celery salt

Notably absent?  

400

Which of these is NOT another name for Interstate I-90

A. Chicago Skyway

B. Dan Ryan Expressway

C. Kennedy Expressway

D. Edens Expressway

E. Jane Addams Memorial Tollway

D, What is the Edens expressway

400

In terms of ridership, this is the busiest EL line

A. Blue

B. Brown

C. Red

C, What is the Red Line (234K weekday rides), followed by the Blue Line, and the Brown Line

400

Everyone knows the Willis Tower is the tallest building in Chicago.  How many years was it the tallest in the world?

A. 1

B. 10

C. 15

D. 25

D, What is 25 years.  The Sears Tower was the tallest building in the world from 1973 to 1998, until the Petronas Towers in Kuala Lumpur were completed in Malaysia.

400

Which of these popular Chicago area music festivals is the longest running?

A. Ravinia Festival

B. Chicago Jazz Festival

C. Chicago Blues Festival

D. Lollapalooza

E. Dillo Day

A, What is Ravinia.  Created in 1904 as an amusement park, it hosted it’s first orchestral performance in 1905.

Jazzfest 1979, Bluesfest 1984, Lollapalooza 1991, Dillo Day 1972. 

400

Which of the following is NOT a decision you need to make when ordering an Italian Beef sandwich?

A. Dry, wet, or dipped

B. Sweet or Hot (peppers)

C. Cheese or no cheese

D. Toasted or not toasted

What is D, toasting is not an option.  Ex:  Beef, Dipped, Sweet, Provolone.

500

Which of these is NOT another name for Interstate I-94

A. Bishop Ford Memorial Freeway

B. Dan Ryan Expressway

C. Kennedy Expressway

D. Edens Expressway

E. Jane Addams Memorial Tollway

E, What is the Jane Addams Memorial Tollway.

500

Which two CTA lines descend from elevated tracks just outside the Loop into subways in the downtown area?

A. Red and Blue

B. Blue and Brown

C. Black and Blue

D. Orange and Red

What A, the Red line and the Blue line.  The Red and Blue lines go 35 feet underground in the downtown area.  The subways were built in (1943 and 1951 respectively) to minimize train traffic on the Loop tracks and speed traffic through the downtown area.

500

Frank Lloyd Wright had some of his most prolific years in the Chicago area.  What architectural style is he most closely connected to?

A. Modern

B. Colonial

C. Prairie

D. Art Deco

C, What is The Prairie Style, which is exemplified by strong horizontals on low lying buildings and houses. There are actually four FLW designed buildings in Evanston:

1014 Hinman Street

1300-02 Davis Street

2420 Harrison Street

2614 Lincolnwood Drive

500

Which of these stage and screen actors were NOT once part of the cast at Second City Chicago?

A. Steve Carrell

B. Stephen Colbert

C. Alan Alda

D. Jimmy Fallon


D, Who is Jimmy Fallon.

Steve Carrell 1991

Stephen Colbert 1993

Alan Alda 1960



500

Which Chicago pizzeria invented deep dish pizza?

A. Pizzeria Uno

B. Lou Malnati’s

C. Giordano’s

D. Gino’s East

What is A or B, it’s still unclear.  Uno’s founder says he is the inventor, but his original pizza chef, Rudy Malnati said it was his idea.