Chicago Magazine has a list of the Top 40 Music Albums by Chicago Artists, defined by them as "We classify a Chicago record as a nonclassical recording by an artist who is local by birthright or who adopted Chicago as home—or at least lived in town at the time the recording was made."
The top 10 are:
10. Kanye West: The College Dropout (2004): Wherein the Oak Lawn kid fulfilled his tremendous promise with intelligent, tongue-twisting rhymes and versatile MC skills.
9. Andrew Bird: The Mysterious Production of Eggs (2005): Bird’s mellow, atmospheric tour de force gleefully thumbs its nose at any genre labels — and mesmerizes for 53 minutes.
8. Louis Armstrong: The Complete Hot Five and Hot Seven Recordings (2000): If you want to know where jazz came from, this treasure-trove of recordings from 1925 to 1929 (when Chicago was the jazz epicenter) is a good place to start.
7. Liz Phair: Exile in Guyville (1993): Equal parts cryptic and desperately blunt, this New Trier grad’s lo-fi indie classic pulses with a deadpan humor and anger that few have ever matched on record.
6. Curtis Mayfield: Superfly (1972): Mayfield’s funky grooves and gritty stories — reflecting his upbringing in the Cabrini-Green projects — captured the sound of inner-city streets without moralizing or glorifying.
5. Muddy Waters: The Chess Box (1989): This 72-song boxed set spanning 25 years is the only way to do justice to the man who, in all his swampy slide-guitar glory, basically invented Chicago blues.
4. Naked Raygun: All Rise (1986): Spawning imitators around town, this artsy, hardcore album throbs with old-school, muscular punk rock—and brains to boot.
3. Smashing Pumpkins: Siamese Dream (1993): Billy Corgan’s attempt to one-up Nirvana resulted in one of the decade’s definitive discs: heavy, dreamy, and layered in sonic noise, it nearly succeeded.
2. Willie Dixon: The Chess Box (1988): The definitive Chicago blues compilation: 36 Dixon-penned classics played by Chess Records’ legendary performers, including Dixon—the best blues songwriter ever.
1. Wilco: Yankee Hotel Foxtrot (2002): Wilco overcame drug problems, infighting, and record-label drama to create an unforgettable album that will define Chicago for generations of music fans. A lush, chaotic record that only gets better with time (and repeated spins), YHF’s weary forays into psychedelia and noise inadvertently caught the post-9/11 anguish better than any other album.