- - u.s. city that was stylish in the past?
- - A city fashionable in the past
- - Large city in Illinois
- - City served by O'Hare and Midway airports
- - city smart and fashionable in former times
- - Largest U.S. city starting with "C"
- - City displaying stylishness in the past
- - Smart attempt to circle a US city
- - stylish silver ring from a city in illinois
- - City in a whirl
- - Silver in elegant old US city
- - The "Windy City" of Illinois
- - US city fashionable in the past
- - Sophisticated earlier city
- - Fashionable to travel round a windy city
- - Illinois city, home to the Lincoln Park Zoo, and host of two International Conferences on Climate Change
- - McDonald's Thanksgiving Parade is celebrated in this city of U.S.
- - Attorney General, initially in elegant old US city
- - US city that was smart in the past
- - City cold: greeting Charlie an effort
- - us city known as 'the windy city'
- - US city — musical featuring All That Jazz
- - City of the Bears and the Bulls
- - Al Capone's city
- - City on Lake Michigan
- - Windy City cutely elegant in the past
- - Windy City
- - Most-populous city of Illinois, the third-largest in the USA
- - City of Illinois
- - The windy city
- - US city showing elegance in the past
- - City in Illinois
- - City said to have big shoulders
- - Fine journey beyond a US city
- - 15 across gets a big job at the bar going around city in America
- - Smart move, going around a city in US
- - Illinois city
- - Trendy barman finds love in American city
- - City's elegance gone
- - US city
- - Smart answer -- leave city!
- - City once fashionable, in a contrary sort of way
- - Trendy in the past in American city
- - New Soldier Field home
- - Illinois city where 18-Across was born
- - Wrigley Field city
- - City for cartoonist Young in the past?
- - Site of Marina City
- - Convention city for 1952.
- - "City of the Big Shoulders."—Sandburg.
- - City where Playboy was founded
- - 1975 musical set in an Illinois city
- - Musical taking its name from an American city
- - Fashionable before Windy City
- - Marx accepted a key to the city
- - musical featuring cell block tango
- - basketball team that won the nba finals three times in a row twice, from 1991-93 and 1996-98
- - "If You Leave Me Now" rock band and recipient of the Grammy Lifetime Achievement Award in 2020
- - once in pursuit of stylish us metropolis
- - kim kardashian's youngest daughter
- - most recent musical to win best picture [2002]
- - band with horns
- - illinois port which houses the sears tower
- - Where Michelle Obama was born
- - 2002 film starring Renee Zellweger as Roxie Hart
- - Musical featuring the song All That Jazz
- - Michigan port appealingly elegant in the past
- - Geographically named band with the 1984 hit "You're the Inspiration"
- - Band with the 1984 hit "Stay the Night"
- - 2002 Oscar-winning musical
- - 1975 Broadway musical that earned Bob Fosse three Tony nominations
- - 1970s' John Kander/Fred Ebb musical
- - Oscar-winning musical
- - Michigan port
- - Where Bulls and Bears are cheered
- - Only musical to win Best Picture since 'Oliver!' in 1968
- - Where the term 'jazz' as applied to jazz music originated
- - Most of the literature previously in America
- - 'All That Jazz' Broadway show
- - Musical fashionable in years gone by
- - With 38-Across, 2016 headline that ended a 108-year streak
- - Musical was fashionable in the past
- - Best Picture of 2002
- - Elegant, a turn in show
- - Lake Michigan metropolis
- - Loop site
- - Running Bear's home
- - Longtime pop group with mostly self-named albums
- - Award-winning Fosse musical
- - "25 or 6 to 4" band
- - 1893 World's Fair setting
- - Hit musical with the song "Razzle Dazzle"
- - "My Kind of Town" subject
- - "You're the Inspiration" rockers
- - Fosse hit
- - 2002 23-Across nominee
- - Hull House home
- - 2002 winner of six Oscars
- - Cubs' home
- - Site for Bulls and Bears
- - Fosse musical
- - ".......... Poems" (Sandburg's first book)
- - Loop locale
- - Bears' home
- - "That Toddling Town"
- - "Hog butcher for the world"
- - Pool game
- - U.S. port.
- - Sandburg poem.
- - Where Comiskey Park is.
- - 4-deal bridge game.
- - Poem by Carl Sandburg.
- - Site of Adler Planetarium.
- - Greatest rail center of U. S.
- - Where Mrs. O'Leary lived.
- - Scene of recent political doings.
- - Victim of Mrs. O'Leary's cow, October, 1871.
- - Former fur trading station near Fort Dearborn.
- - County seat of Cook County, Ill.
- - "Saturday in the Park" band
- - Theme of this puzzle
- - Al Capone's notorious town
- - Birthplace of deep-dish pizza
- - musical that includes the song mister cellophane
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