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Used 1999 Chevrolet 2500 trucks for sale near Chicago, IL

Filters 4 Year Model Price & payment Make Mileage All filters
1 match All miles from 60608
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Est. $400 /mo*
Down Payment
$0
Net trade-in value
$0
Months
72
APR
7.0%
Sales tax
0.0%

*Estimated payments are calculated by Cars.com and are for informational purposes only. We’ve estimated your taxes based on your provided ZIP code. These estimates do not include title, registration fees, lien fees, or any other fees that may be imposed by a governmental agency in connection with the sale and financing of the vehicle. Other taxes may apply. They do not represent a financing offer or a guarantee of credit from the seller. Actual terms vary by lender.

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1999 Chevrolet 2500
1999 Chevrolet 2500
1999 Chevrolet 2500
1999 Chevrolet 2500
1999 Chevrolet 2500
1999 Chevrolet 2500 View all 48 photos

Used

1999 Chevrolet 2500

0 mi.
$24,900 $1,000 price drop
Est. $468/mo*
Get the AutoCheck Report
SuperSport Classics
Not rated Dealerships need five reviews in the past 24 months before we can display a rating. (1 review)
Largo, FL (1,005 mi.)
Call Check availability Check availability

Vehicle information

Ext. color: Indigo Blue Metallic
Int. color: Blue
Drivetrain: Rear-wheel Drive
Fuel type: Gasoline
Transmission: Automatic
Engine: Vortec 5.7L V-8 regular unleaded, engine with 255HP
Stock #: 2575
VIN: 1GCGC23R5XF005729

Reviews

SuperSport Classics review

Very impressed when I first arrived.

September 28, 2025
By Stan from Knoxville TN

Very impressed when I first arrived. Great selection, full service dealership, good prices, knowledgeable and courteous staff, also open on weekends

1999 Chevrolet 2500 review

I like this truck just wanted a diffrent color

February 12, 2020
By JDaddy from Bryan Tx
Test drove this car

I like this truck . Just want 4 dors and less miles for the price . But i will return for the customer service . IT was top notch.

There are 6 matching cars close to your year range.

1997 Chevrolet 2500
1997 Chevrolet 2500
1997 Chevrolet 2500
1997 Chevrolet 2500
1997 Chevrolet 2500
1997 Chevrolet 2500 View all 30 photos

Used

1997 Chevrolet 2500

104,078 mi.
$17,500
Est. $329/mo*
Free CARFAX Report
Stevenson-Hendrick Honda Wilmington
Wilmington, NC (749 mi.)
Call Check availability Check availability

Vehicle information

Ext. color: Summit White
Int. color: Neutral
Drivetrain: Four-wheel Drive
Fuel type: Gasoline
Transmission: Automatic
Engine: Gas V8 5.7L/350
Stock #: P12379
VIN: 1GCGK24R3VZ197701

Features

Convenience: Keyless Entry
Exterior: Tow Hooks
Seating: Leather Seats
1997 Chevrolet 2500 K2500 Silverado
1997 Chevrolet 2500 K2500 Silverado
1997 Chevrolet 2500 K2500 Silverado
1997 Chevrolet 2500 K2500 Silverado
1997 Chevrolet 2500 K2500 Silverado
1997 Chevrolet 2500 K2500 Silverado View all 21 photos

Used

1997 Chevrolet 2500 K2500 Silverado

241,108 mi.
$3,988 $1,000 price drop
Free CARFAX Report
Patriot Auto Sales LLC
Cheyenne, WY (888 mi.)
Call Check availability Check availability

Vehicle information

Ext. color: Summit White
Int. color: Gray
Drivetrain: Four-wheel Drive
Fuel type: Gasoline
Transmission: Automatic
Engine: 7.4L V-8 regular unleaded, engine with 290HP
Stock #: W1945
VIN: 1GCGK29R0VE259989

Features

Exterior: Tow Hooks
1998 Chevrolet 2500 Fleetside
1998 Chevrolet 2500 Fleetside
1998 Chevrolet 2500 Fleetside
1998 Chevrolet 2500 Fleetside
1998 Chevrolet 2500 Fleetside
1998 Chevrolet 2500 Fleetside View all 10 photos

Used

1998 Chevrolet 2500 Fleetside

274,097 mi.
$10,950
Est. $206/mo*
Free CARFAX Report
Tavern Motors
Laurens, SC (589 mi.)
Call Check availability Check availability

Vehicle information

Ext. color: Copper
Int. color: Tan
Drivetrain: Rear-wheel Drive
MPG: 14-18
Fuel type: Gasoline
Transmission: Automatic
Engine: Vortec 7.4L V-8 regular unleaded, engine with 290HP
Stock #: 98chv2500
VIN: 1GCGC29J1WE117806
No photo available

Used

2000 Chevrolet 2500 Crew-Cab Short-Bed 4X4 - LBZ DURAMAX DIESEL SWAP!

214,798 mi.
$22,997
Est. $432/mo*
Get the AutoCheck Report
Thiel Motor Sales Inc.
De Witt, IA (149 mi.)
Call Check availability Check availability

Vehicle information

Ext. color: White
Int. color: Charcoal
Drivetrain: Four-wheel Drive
Fuel type: Diesel
Transmission: Automatic
Engine: 6.6L LBZ Duramax Diesel
Stock #: 451945
VIN: 1GCGC23R9YF451945
No photo available

Used

1998 Chevrolet 2500 Fleetside

176,040 mi.
$7,800
Est. $147/mo*
Free CARFAX Report
Coughlin Chevy, GMC, Buick
London, OH (260 mi.)
Call Check availability Check availability

Vehicle information

Ext. color: Indigo Blue Metallic
Int. color: Gray
Drivetrain: Four-wheel Drive
Fuel type: Gasoline
Transmission: Automatic
Engine: 7.4L V-8 regular unleaded, engine with 290HP
Stock #: GA26541B
VIN: 1GCGK29R4WE237141

Features

Convenience: Keyless Entry
Entertainment: CD Player
Exterior: Tow Hitch, Tow Hooks
1997 Chevrolet 2500 Silverado
1997 Chevrolet 2500 Silverado
1997 Chevrolet 2500 Silverado
1997 Chevrolet 2500 Silverado
1997 Chevrolet 2500 Silverado
1997 Chevrolet 2500 Silverado View all 7 photos

Used

1997 Chevrolet 2500 Silverado

0 mi.
$7,750
Est. $146/mo*
Get the AutoCheck Report
CAP Enterprises
Sioux Falls, SD (475 mi.)
Call Check availability Check availability

Vehicle information

Ext. color: White
Int. color: Gray
Drivetrain: Four-wheel Drive
Fuel type: Gasoline
Transmission: 4-Speed Automatic
Engine: 5.7L V8 16V MPFI OHV
Stock #: 216328
VIN: 1GCGK24R5VZ216328
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About the 1999 Chevrolet 2500

FAQs

How much does the 1999 Chevrolet 2500 cost?

The 1999 Chevrolet 2500 price depends on several factors, including the trim level, optional features, mileage, vehicle history and location. The nationwide average price for a 1999 2500 is $24,900, with pricing starting at $24,900.

What are some similar vehicles and competitors of the 1999 Chevrolet 2500?

The 1999 Chevrolet 2500 compares to and/or competes against the following vehicles:

Is the 1999 Chevrolet 2500 reliable?

The 1999 Chevrolet 2500 has an average reliability rating of 4.3 out of 5 according to Cars.com consumers. Find real-world reliability insights within consumer reviews from 1999 2500 owners.

Ratings (4 reviews)

100% of drivers recommend this car

Rating breakdown (out of 5):
  • Comfort 4.8
  • Interior 4.5
  • Performance 4.8
  • Value 4.5
  • Exterior 4.5
  • Reliability 4.3

*Estimated payments are calculated by Cars.com and are for informational purposes only. We’ve estimated your taxes based on your provided ZIP code. These estimates do not include title, registration fees, lien fees, or any other fees that may be imposed by a governmental agency in connection with the sale and financing of the vehicle. Other taxes may apply. They do not represent a financing offer or a guarantee of credit from the seller. Actual terms vary by lender.

**Your Saved Vehicles list will be shared along with your contact information when you submit a vehicle request to a dealership. To opt out of this sharing, please view your options on Cars.com Privacy Notice.

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