The average asking price for a used 1999 Chevrolet Silverado 2500 is $16,162, with 124,190 miles on average, across 11 cars for sale at U.S. dealers as of Nov 10, 2026.
Used 1999 Chevrolet Silverado 2500s for sale at U.S. dealers ask $16,162 on average (half ask less than $15,999), across 11 cars. The cars for sale have 124,190 miles on average: one with fewer miles is worth more, and one with more is worth less. To check one car's price against cars of its trim and mileage, enter its VIN in OttoQuest's free Deal Check.
The 1999 asks $16,162 on average with 124,190 miles; the 1998 asks $11,586 with 166,106 miles, and the 2000 asks $10,291 with 174,482 miles.
Used and certified cars for sale at US dealers, each car counted once. Days listed are the dealer’s own days on market where they publish it. Price moves compare the same cars at both ends of the window.
| $24,271 |
| 153,564 |
| 185 |
| 2014 | $21,622 | 158,219 | 35 |
| 2013 | $18,340 | 162,456 | 86 |
| 2012 | $16,190 | 182,771 | 48 |
| 2011 | $16,506 | 189,459 | 68 |
| 2010 | $17,751 | 158,632 | 14 |
| 2009 | $11,890 | 174,787 | 34 |
| 2008 | $15,321 | 181,637 | 43 |
| 2007 | $17,073 | 172,574 | 69 |
| 2006 | $16,951 | 185,018 | 50 |
| 2005 | $17,671 | 165,683 | 73 |
| 2004 | $15,742 | 174,774 | 61 |
| 2003 | $13,611 | 172,759 | 40 |
| 2002 | $13,908 | 161,554 | 34 |
| 2001 | $10,215 | 182,847 | 22 |
| 2000 | $10,291 | 174,482 | 16 |
| 1999 | $16,162 | 124,190 | 11 |
| 1998 | $11,586 | 166,106 | 6 |
| 1997 | $24,450 | 79,279 | 2 |
| 1996 | $15,647 | 211,987 | 2 |
| 1995 | $12,900 | 157,224 | 6 |
| 1994 | $13,266 | 194,574 | 3 |
| 1993 | $15,000 | — | 1 |
| 1992 | $9,369 | 168,989 | 5 |
| 1989 | $19,900 | 116,000 | 1 |
| 1988 | $9,247 | 151,512 | 2 |
