Winner of a National Magazine Award in 2004 and a gold medal in 2005 from the City and Regional Magazine Association
Chicago magazine has often been singled out by its peers for top awards in its circulation category. In 2004, Chicago won the National Magazine Award for General Excellence (circulation 100,000-250,000), the first monthly city magazine ever to be so honored. In 2006, the magazine was again a finalist for this prestigious honor. In 2005, the magazine won the gold award for General Excellence (circulation 100,000 and above) from the City and Regional Magazine Association and was a finalist in 2006. Here are some other recent honors won by Chicago:
| City and Regional Magazine Association (CRMA) | ||
| 2007 | Gold | Reporting |
| Gold | Writer of the Year | |
| Silver | Special Issue | |
| Silver | Leisure Interests | |
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| Silver | Ancillary Publication |
| 2006 | Gold | Feature Story |
| Gold | Civic Journalism | |
|
| Silver | Special Issue |
| 2005 | Gold | Food/Dining Criticism |
| Gold | Spread Design | |
| Silver | Feature Design | |
| Silver | Feature Writing | |
| Bronze | Writer of the Year | |
| 2004 | Gold | Food/Dining Criticism |
| Silver | Reporting | |
| Bronze | Personality Profile | |
| 2003 | Gold | Reporting |
| Gold | Personality Profile | |
| Silver | Spread Design | |
| Bronze | Writer of the Year | |
| Peter Lisagor Awards | ||
2007 | First Place | In-depth Reporting |
| 2005 | First Place | Business and Consumer Reporting |
| First Place | In-depth Reporting | |
| 2004 | First Place | In-depth Reporting |
| First Place | Sports Journalism Reporting | |
| First Place | News Design Magazine | |
| 2003 | First Place | In-depth Reporting |
| First Place | Features | |
| First Place | Columns and Commentary | |
| John Bartlow Martin Award | ||
| 2003 | Second Place | Public Interest Journalism |
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