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| Episode | Episode Name | Air Date | | 1 | Chicago: Episode 1 | Tue Jan 15, 2002 | | 2 | Chicago: Episode 2 | Tue Jan 15, 2002 | | 3 | Chicago: Episode 3 | Tue Jan 22, 2002 | | 4 | Chicago: Episode 4 | Tue Jan 29, 2002 | | 5 | Chicago: Episode 5 | Tue Feb 05, 2002 | | 6 | Chicago: Episode 6 | Tue Feb 12, 2002 | | 7 | Chicago: Episode 7 | Tue Feb 19, 2002 | | 8 | Chicago: Episode 8 | Tue Mar 05, 2002 | | 9 | Chicago: Episode 9 | Tue Mar 12, 2002 | | 10 | Chicago: Episode 10 | Tue Mar 19, 2002 | | 11 | Chicago: Episode 11 | Tue Mar 26, 2002 | | 12 | Chicago: Episode 12 | Tue Apr 02, 2002 | | 13 | Chicago: Episode 13 | Tue Apr 09, 2002 | | 14 | Chicago: Episode 14 | Tue Apr 23, 2002 | | 15 | Chicago: Episode 15 | Tue Apr 30, 2002 | | 16 | Chicago: Episode 16 | Tue May 07, 2002 | | 17 | Chicago: Episode 17 | Tue May 21, 2002 | | 18 | Chicago: Episode 18 | Tue May 28, 2002 | | 19 | Chicago: Episode 19 | Tue Jun 04, 2002 | | 20 | Chicago: Episode 20 | Tue Jun 11, 2002 | | 21 | Chicago: Episode 21 | Tue Jun 18, 2002 | | 22 | Chicago: Episode 22 | Tue Jun 25, 2002 | | 23 | Chicago: Episode 23 | Tue Jul 02, 2002 | | 24 | Chicago: Episode 24 | Tue Jul 09, 2002 | | 25 | The Real World Chicago Reunion Special | Tue Jul 16, 2002 | | Special | A Decade of Bloopers | Tue May 28, 2002 | | Special | Lazy, Sexy, Naked, Drunk: The Real World Guide To Being the Perfect Roommate | Tue Jan 08, 2002 | | Special | The Real World Chicago Casting Special | Tue Jan 08, 2002 |
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