Home
Search
Saved
Research
More
Home
Search
Saved
Guides & Reviews
News & Analysis
Sell My Car
Settings
Get the App
Pickup Trucks for Sale in Chicago, IL
sort
filter
Truck
50 Miles Away
Clear filters
Clear filters
Save search
Location & Radius
Select location
50 miles
Select location
50 miles
Vehicle 1
All makes & models
Select Trim
All makes & models
Select Trim
Clear
Vehicle 2
All makes & models
Select Trim
All makes & models
Select Trim
Clear
Vehicle 3
All makes & models
Select Trim
All makes & models
Select Trim
Clear
Year Range
to
Price Range
to
Hide listings with no price
Max Mileage
0 mi.
Body Styles
Doors
2
3
4
Body Types
Convertible
(1,599)
Coupes
(2,915)
Crossover
(27,689)
Hatchbacks
(1,760)
Minivans
(3,597)
Passenger/Cargo Vans
(2,832)
Sedans
(19,523)
SUVs
(54,665)
Trucks
(14,136)
Wagons
(504)
Engine & Fuel
Fuel Efficiency
Any MPG
Any MPG
Fuel Type
Electric
(214)
Diesel
(1,422)
Gasoline
(10,253)
Hybrid
(652)
Hydrogen fuel cell
(0)
Natural gas
(0)
Plug-in hybrid
(0)
Cylinders
2
3
4
5
6
8
10
12
Transmission
Automatic
(13,843)
Manual
(39)
Drivetrain
Front wheel drive (FWD)
(74)
Rear wheel drive (RWD)
(579)
All wheel drive (AWD)
(1,583)
Four wheel drive (4WD)
(11,811)
Features & Technology
Backup camera
(9,671)
Bluetooth
(9,031)
Entertainment/DVD
(626)
Handicap accessible
(0)
Leather
(6,014)
Navigation system
(7,288)
Sunroof / Moonroof
(4,323)
3rd row seats
(7)
Towing
(8,131)
Condition
New
(7,950)
Used
(5,432)
CPO (Certified Pre-Owned)
(754)
colors
exterior
White
(4.2k)
Gray
(2.7k)
Black
(3.1k)
Yellow
(15)
Orange
(44)
Brown
(177)
Red
(1k)
Green
(229)
Blue
(1.1k)
Purple
(2)
Silver
(945)
Gold
(18)
interior
White
(13)
Gray
(2.1k)
Black
(9.3k)
Brown
(514)
Red
(74)
Blue
(539)
Vehicle Category
Any Category
Any Category
Truck Options
Cabin Type
Extended
(944)
Regular
(1,098)
Crew
(11,740)
Rear Wheel
Single
(13,774)
Dual
(285)
Bed Type
Short
(185)
Regular
(5,209)
Chassis
(0)
Step-Side
(0)
Long
(199)
Search Options
Hide 'online only' listings
location
Select location
radius
50 miles
sort by
Distance (Closest first)
sort
filter
14,136
vehicles found
Truck
50 Miles Away
Clear filters
Need help finding the right vehicle?
Help me search
2020 Chevrolet Silverado 1500 LT Trail Boss
77,300 Miles
Chicago, IL
HIGH PRICE
High Quality Auto Sales
HIGH PRICE
282
days on market
$36,995
Fees may apply
est. $640/mo
HIGH PRICE
Request Info
Request Info
Year:
2020
Make:
Chevrolet
Model:
Silverado 1500
Body type:
pickup
Doors:
4
Drivetrain:
4X4
Exterior color:
silver
Combined gas mileage:
17
Fuel type:
gasoline
Interior color:
black
Transmission:
automatic
Mileage:
77300
VIN:
1GCPYFEL0LZ200275
2023 Chevrolet Silverado 1500 LT Trail Boss
49,368 Miles
Chicago, IL
NO RATING
High Quality Auto Group
NO RATING
24
days on market
$44,995
Fees may apply
est. $778/mo
NO RATING
Request Info
Request Info
Year:
2023
Make:
Chevrolet
Model:
Silverado 1500
Body type:
pickup
Doors:
4
Drivetrain:
4X4
Exterior color:
brown
Combined gas mileage:
17
Fuel type:
gasoline
Interior color:
brown
Transmission:
automatic
Mileage:
49368
VIN:
3GCUDFED9PG162431
2014 Ram 1500 Laramie
150,045 Miles
Chicago, IL
OVERPRICED
USA Auto And Truck
OVERPRICED
28
days on market
$19,990
Fees may apply
est. $346/mo
OVERPRICED
Request Info
Request Info
Year:
2014
Make:
Ram
Model:
1500
Body type:
pickup
Doors:
4
Drivetrain:
4X4
Exterior color:
brown
Combined gas mileage:
22
Fuel type:
diesel
Interior color:
brown
Transmission:
automatic
Mileage:
150045
VIN:
1C6RR7NM1ES355800
2026 Toyota Tacoma TRD Sport
7,530 Miles
Chicago, IL
FAIR DEAL
High Quality Auto Group
FAIR DEAL
5
days on market
$46,875
Fees may apply
est. $811/mo
FAIR DEAL
Request Info
Request Info
Year:
2026
Make:
Toyota
Model:
Tacoma
Body type:
pickup
Doors:
4
Drivetrain:
4X4
Exterior color:
brown
Combined gas mileage:
Fuel type:
gasoline
Interior color:
black
Transmission:
automatic
Mileage:
7530
VIN:
3TMLB5JN0TM214552
2022 Chevrolet Silverado 1500 Limited RST
55,743 Miles
Chicago, IL
OVERPRICED
High Quality Auto Group
OVERPRICED
24
days on market
$43,995
Fees may apply
est. $761/mo
OVERPRICED
Request Info
Request Info
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500 Limited
Body type:
pickup
Doors:
4
Drivetrain:
4X4
Exterior color:
black
Combined gas mileage:
17
Fuel type:
gasoline
Interior color:
black
Transmission:
automatic
Mileage:
55743
VIN:
1GCUYEED6NZ191753
2022 Chevrolet Silverado 1500 ZR2
74,175 Miles
Chicago, IL
HIGH PRICE
High Quality Auto Group
HIGH PRICE
24
days on market
$45,995
Fees may apply
est. $796/mo
HIGH PRICE
Request Info
Request Info
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
pickup
Doors:
4
Drivetrain:
4X4
Exterior color:
blue
Combined gas mileage:
15
Fuel type:
gasoline
Interior color:
black
Transmission:
automatic
Mileage:
74175
VIN:
3GCUDHEL0NG684414
2018 Chevrolet Silverado 1500 LT
101,339 Miles
Chicago, IL
OVERPRICED
High Quality Auto Group
OVERPRICED
47
days on market
$24,995
Fees may apply
est. $432/mo
OVERPRICED
Request Info
Request Info
Year:
2018
Make:
Chevrolet
Model:
Silverado 1500
Body type:
pickup
Doors:
4
Drivetrain:
4X4
Exterior color:
gray
Combined gas mileage:
18
Fuel type:
gasoline
Interior color:
black
Transmission:
automatic
Mileage:
101339
VIN:
1GCVKREC8JZ214142
2023 Chevrolet Silverado 1500 Custom Trail Boss
39,517 Miles
Chicago, IL
NO RATING
High Quality Auto Group
NO RATING
14
days on market
$39,995
Fees may apply
est. $692/mo
NO RATING
Request Info
Request Info
Year:
2023
Make:
Chevrolet
Model:
Silverado 1500
Body type:
pickup
Doors:
4
Drivetrain:
4X4
Exterior color:
blue
Combined gas mileage:
17
Fuel type:
gasoline
Interior color:
black
Transmission:
automatic
Mileage:
39517
VIN:
3GCUDCED8PG135803
fresh
fresh
2019 Chevrolet Silverado 1500 LT Trail Boss
38,738 Miles
Chicago, IL
UNCERTAIN
High Quality Auto Group
UNCERTAIN
1
day on market
$45,995
Fees may apply
est. $796/mo
UNCERTAIN
fresh
Request Info
Request Info
Year:
2019
Make:
Chevrolet
Model:
Silverado 1500
Body type:
pickup
Doors:
4
Drivetrain:
4X4
Exterior color:
white
Combined gas mileage:
17
Fuel type:
gasoline
Interior color:
red
Transmission:
automatic
Mileage:
38738
VIN:
1GCPYFED3KZ357743
2019 Ford F-150 XL
137,554 Miles
Chicago, IL
GREAT DEAL
USA Auto And Truck
GREAT DEAL
37
days on market
$16,990
Fees may apply
est. $294/mo
GREAT DEAL
Request Info
Request Info
Year:
2019
Make:
Ford
Model:
F-150
Body type:
pickup
Doors:
4
Drivetrain:
4X4
Exterior color:
red
Combined gas mileage:
21
Fuel type:
gasoline
Interior color:
gray
Transmission:
automatic
Mileage:
137554
VIN:
1FTEW1EP9KFB91689
2014 Ram 1500 Sport
167,135 Miles
Chicago, IL
GREAT DEAL
USA Auto And Truck
GREAT DEAL
177
days on market
$10,990
Fees may apply
est. $190/mo
GREAT DEAL
Request Info
Request Info
Year:
2014
Make:
Ram
Model:
1500
Body type:
pickup
Doors:
4
Drivetrain:
4X4
Exterior color:
black
Combined gas mileage:
17
Fuel type:
gasoline
Interior color:
black
Transmission:
automatic
Mileage:
167135
VIN:
1C6RR7UT2ES462539
2014 Chevrolet Silverado 1500 LT
149,539 Miles
Chicago, IL
FAIR DEAL
USA Auto And Truck
FAIR DEAL
91
days on market
$14,990
Fees may apply
est. $259/mo
FAIR DEAL
Request Info
Request Info
Year:
2014
Make:
Chevrolet
Model:
Silverado 1500
Body type:
pickup
Doors:
4
Drivetrain:
4X4
Exterior color:
silver
Combined gas mileage:
13
Fuel type:
flex fuel
Interior color:
black
Transmission:
automatic
Mileage:
149539
VIN:
3GCUKREC3EG475664
2015 Chevrolet Colorado Z71
144,179 Miles
Chicago, IL
FAIR DEAL
USA Auto And Truck
FAIR DEAL
58
days on market
$14,990
Fees may apply
est. $259/mo
FAIR DEAL
Request Info
Request Info
Year:
2015
Make:
Chevrolet
Model:
Colorado
Body type:
pickup
Doors:
4
Drivetrain:
4X4
Exterior color:
silver
Combined gas mileage:
20
Fuel type:
gasoline
Interior color:
black
Transmission:
automatic
Mileage:
144179
VIN:
1GCGTCE33F1122591
2016 Chevrolet Silverado 1500 Work Truck
162,579 Miles
Chicago, IL
GOOD DEAL
USA Auto And Truck
GOOD DEAL
188
days on market
$10,990
Fees may apply
est. $190/mo
GOOD DEAL
Request Info
Request Info
Year:
2016
Make:
Chevrolet
Model:
Silverado 1500
Body type:
pickup
Doors:
4
Drivetrain:
4X4
Exterior color:
white
Combined gas mileage:
18
Fuel type:
gasoline
Interior color:
gray
Transmission:
automatic
Mileage:
162579
VIN:
1GCVKNEC2GZ202201
2015 GMC Sierra 1500 SLE
158,149 Miles
Chicago, IL
GOOD DEAL
USA Auto And Truck
GOOD DEAL
135
days on market
$12,990
Fees may apply
est. $225/mo
GOOD DEAL
Request Info
Request Info
Year:
2015
Make:
GMC
Model:
Sierra 1500
Body type:
pickup
Doors:
4
Drivetrain:
RWD
Exterior color:
black
Combined gas mileage:
19
Fuel type:
gasoline
Interior color:
black
Transmission:
automatic
Mileage:
158149
VIN:
3GTU1UECXFG124919
2016 GMC Canyon SLT
133,616 Miles
Chicago, IL
GOOD DEAL
USA Auto And Truck
GOOD DEAL
15
days on market
$14,990
Fees may apply
est. $259/mo
GOOD DEAL
Request Info
Request Info
Year:
2016
Make:
GMC
Model:
Canyon
Body type:
pickup
Doors:
4
Drivetrain:
RWD
Exterior color:
gray
Combined gas mileage:
21
Fuel type:
gasoline
Interior color:
black
Transmission:
automatic
Mileage:
133616
VIN:
1GTG5DE38G1183243
2020 GMC Sierra 1500 Elevation
79,881 Miles
Chicago, IL
UNCERTAIN
High Quality Auto Group
UNCERTAIN
89
days on market
$39,995
Fees may apply
est. $692/mo
UNCERTAIN
Request Info
Request Info
Year:
2020
Make:
GMC
Model:
Sierra 1500
Body type:
pickup
Doors:
4
Drivetrain:
4X4
Exterior color:
blue
Combined gas mileage:
19
Fuel type:
gasoline
Interior color:
black
Transmission:
automatic
Mileage:
79881
VIN:
1GTU9CED5LZ133972
2016 Ram 1500 Big Horn
109,215 Miles
Chicago, IL
GOOD DEAL
Blue Sky Automotive - Ch...
GOOD DEAL
84
days on market
$16,353
Fees may apply
est. $283/mo
GOOD DEAL
Request Info
Request Info
Year:
2016
Make:
Ram
Model:
1500
Body type:
pickup
Doors:
4
Drivetrain:
4X4
Exterior color:
Combined gas mileage:
17
Fuel type:
gasoline
Interior color:
gray
Transmission:
automatic
Mileage:
109215
VIN:
1C6RR7LT2GS117161
2019 Chevrolet Silverado 1500 LD LT
134,590 Miles
Chicago, IL
GOOD DEAL
Blue Sky Auto Sales - Br...
GOOD DEAL
20
days on market
$16,995
Fees may apply
est. $294/mo
GOOD DEAL
Request Info
Request Info
Year:
2019
Make:
Chevrolet
Model:
Silverado 1500 LD
Body type:
pickup
Doors:
4
Drivetrain:
4X4
Exterior color:
black
Combined gas mileage:
Fuel type:
gasoline
Interior color:
black
Transmission:
automatic
Mileage:
134590
VIN:
2GCVKPEC2K1156172
2019 Ram 1500 Classic Tradesman
209,305 Miles
Chicago, IL
FAIR DEAL
Blue Sky Auto Sales - Br...
FAIR DEAL
104
days on market
$7,995
Fees may apply
est. $138/mo
FAIR DEAL
Request Info
Request Info
Year:
2019
Make:
Ram
Model:
1500 Classic
Body type:
pickup
Doors:
2
Drivetrain:
RWD
Exterior color:
white
Combined gas mileage:
14
Fuel type:
flex fuel
Interior color:
gray
Transmission:
automatic
Mileage:
209305
VIN:
3C6JR6DG3KG709368
1
2
3
...
707
Chicago, IL DEALER RATINGS & REVIEWS
Be the first to write about your experience!
Write a review
TRUCK
Used Pickup Trucks for Sale
TRUCK BY PRICE
Pickup Trucks for Sale under $1,000
Pickup Trucks for Sale under $10,000
Pickup Trucks for Sale under $100,000
Pickup Trucks for Sale under $11,000
Pickup Trucks for Sale under $12,000
Pickup Trucks for Sale under $13,000
Pickup Trucks for Sale under $14,000
Pickup Trucks for Sale under $15,000
Pickup Trucks for Sale under $16,000
Pickup Trucks for Sale under $17,000
Pickup Trucks for Sale under $18,000
Pickup Trucks for Sale under $19,000
Pickup Trucks for Sale under $2,000
Pickup Trucks for Sale under $20,000
Pickup Trucks for Sale under $25,000
Pickup Trucks for Sale under $3,000
Pickup Trucks for Sale under $30,000
Pickup Trucks for Sale under $35,000
Pickup Trucks for Sale under $4,000
Pickup Trucks for Sale under $40,000
Pickup Trucks for Sale under $45,000
Pickup Trucks for Sale under $5,000
Pickup Trucks for Sale under $50,000
Pickup Trucks for Sale under $6,000
Pickup Trucks for Sale under $60,000
Pickup Trucks for Sale under $7,000
Pickup Trucks for Sale under $70,000
Pickup Trucks for Sale under $8,000
Pickup Trucks for Sale under $80,000
Pickup Trucks for Sale under $9,000
Pickup Trucks for Sale under $90,000