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 2005, the magazine won the gold award for General Excellence (circulation 100,000 and above) from the City and Regional Magazine Association. Here are some other honors won by Chicago in recent years:
| City and Regional Magazine Association (CRMA) | ||
| 2012 | Gold | Food/Dining Writing |
| Gold | Reader Service | |
| 2011 | Gold | Excellence online |
| Gold | Blog Column | |
| 2010 | Gold | Reader Service |
| Gold | Special Issue | |
| Gold | Blog Column | |
| Gold | E-Newsletter Results | |
| 2009 | Gold | Community Service |
| Gold | Multimedia | |
| 2008 | Bronze | Regular Column |
| Bronze | Photo Essay | |
| Bronze | Civic Journalism | |
| 2007 | Gold | Reporting |
| Gold | Writer of the Year | |
| Gold | Writer of the Year | |
| Silver | Special Issue | |
| Silver | Leisure Interest | |
| 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 | |
| Peter Lisagor Awards | ||
| 2012 | First Place | Feature Writing |
| First Place | In-Depth Reporting | |
| 2011 | First Place | Feature Writing |
| First Place | Arts Reporting and Criticism | |
| First Place | Sports Story | |
| 2010 | First Place | Feature Writing |
| 2007 | First Place | In-Depth Reporting |
| 2005 | First Place | Business and Consumer Reporting |
| First Place | In-Depth Reporting | |
| Herman Kogan Awards (Chicago Bar Assn.) | ||
| 2011 | Award | Print Category |
| Webby Awards | ||
| 2010 | Honoree | Chicagomag.com |
| 2009 | Honoree | Chicagomag.com |
| 2008 | Honoree | Chicagomag.com |
| Media Kit |
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