Oprah is an obvious choice. The TV mogul has given out so many free cars that it only makes sense to put her face on the 20.
Hillary could very well be the next president, which is a big step in getting one's face published on legal tender. Born and raised on the North Side, she's brought Chicago-style politics to Washington for more than 20 years.
Brooks was the first African-American to win a Pulitzer. She hailed Chicago through and through while inspiring a generation of writers.
Out of everyone on this list, Addams probably has the most realistic chance of getting her face on the bill. She was a big player in the women's suffrage movement and the first woman to be awarded the Nobel Peace Prize.
Byrne was Chicago's first and only female mayor. She faced relentless misogyny while in office, but brought meaningful change to the city in spite of it.
While she isn't originally from Chicago and no longer lives here, Fey got her start as an improv comic at The Second City. She's regularly referenced the city in her work, including using Evanston as the setting for Mean Girls. Chicago can definitely take credit for the rise of one of America's funniest people.
The First Lady might not have the resume of her husband, but she did play a big role in creating the Task Force on Childhood Obesity. Perhaps having her face on the bill will remind Americans to stop eating garbage.
Chicago's late First Lady was a major proponent of green spaces across the city, and now has a glorious park named in her honor. If her portrait makes it onto the 20, Chicagoans will be able to remember her while they pay for rental skates at the park's ice ribbon.
Among many of Rhimes's projects is the hit series Scandal, which is partially based on a former aide to President George H. W. Bush. Politicians might be wise to put her face on the 20 as a gesture of good faith to avoid their own sexual endeavors being appropriated for a massive audience.
Crawford is originally from suburban DeKalb, but got her first big break in the city. Why would you print a picture of a crusty old dude when you have a model as an option?
Legend has it O'Leary's cow started the Great Chicago Fire in 1871 by tipping over a lantern in the family's barn. If you disregard the lives destroyed and lost in the event, the burning of the city was a blessing. It gave way to a restructuring of Chicago's infrastructure and allowed it to become the "best planned city in the world."