Skip to main content
Filters

Used Pickup Trucks in Chicago, IL for Sale

8,102 Matches

2017 GMC Sierra 2500 Denali

$60,998•98K mi

Free Shipping from CarMax Schaumburg, IL

Key Features
Bed Cover, 4WD/AWD, Leather Seats, BOSE Sound System, Satellite Radio Ready, Parking Sensors
Location: CarMax Schaumburg in Chicago, Illinois 60173
Description: Used 2017 GMC Sierra 2500 Denali for sale - $60,998, 97,710 miles with Bed Cover, 4WD/AWD, Leather Seats, BOSE Sound System, Satellite Radio Ready, Parking Sensors
Transmission: Automatic Color:Black Interior Color: Black Average Vehicle Review: (0 reviews)

2015 Chevrolet Silverado 1500 High Country

$37,998•103K mi

Free Shipping from CarMax Naperville, IL

Key Features
Bed Cover, 4WD/AWD, Leather Seats, BOSE Sound System, Satellite Radio Ready, Parking Sensors
Location: CarMax Naperville in Naperville, Illinois 60563
Description: Used 2015 Chevrolet Silverado 1500 High Country for sale - $37,998, 102,487 miles with Bed Cover, 4WD/AWD, Leather Seats, BOSE Sound System, Satellite Radio Ready, Parking Sensors
Transmission: Automatic Color:Black Interior Color: Brown Average Vehicle Review: (4.470588235294118 reviews)

2014 Chevrolet Silverado 1500 Work Truck

$27,998•36K mi

Free Shipping from CarMax Naperville, IL

Key Features
Flex Fuel Vehicle, Satellite Radio Ready, Running Boards, Auxiliary Audio Input, Overhead Airbags, Traction Control
Location: CarMax Naperville in Naperville, Illinois 60563
Description: Used 2014 Chevrolet Silverado 1500 Work Truck for sale - $27,998, 35,059 miles with Flex Fuel Vehicle, Satellite Radio Ready, Running Boards, Auxiliary Audio Input, Overhead Airbags, Traction Control
Transmission: Automatic Color:Black Interior Color: Gray Average Vehicle Review: (4.352941176470588 reviews)

2020 Ford F350 XLT

$63,998•91K mi

Free Shipping from CarMax Schaumburg, IL

Key Features
FX4 Package, Long Bed, Fifth Wheel Tow Hitch, 4WD/AWD, Satellite Radio Ready, Rear View Camera
Location: CarMax Schaumburg in Chicago, Illinois 60173
Description: Used 2020 Ford F350 XLT for sale - $63,998, 90,100 miles with FX4 Package, Long Bed, Fifth Wheel Tow Hitch, 4WD/AWD, Satellite Radio Ready, Rear View Camera
Transmission: Automatic Color:White Interior Color: Gray Average Vehicle Review: (0 reviews)

2018 Ford F350 Lariat

$62,998•37K mi

Free Shipping from CarMax Schaumburg, IL

Key Features
Gooseneck Tow Hitch, Leather Seats, Satellite Radio Ready, Parking Sensors, Rear View Camera, Navigation System
Location: CarMax Schaumburg in Chicago, Illinois 60173
Description: Used 2018 Ford F350 Lariat for sale - $62,998, 36,518 miles with Gooseneck Tow Hitch, Leather Seats, Satellite Radio Ready, Parking Sensors, Rear View Camera, Navigation System
Transmission: Automatic Color:Red Interior Color: Black Average Vehicle Review: (0 reviews)

2017 Ford F250 Lariat

$56,998•55K mi

On hold at CarMax Naperville, IL

Key Features
Flex Fuel Vehicle, 4WD/AWD, Leather Seats, Satellite Radio Ready, Parking Sensors, Rear View Camera
Location: CarMax Naperville in Naperville, Illinois 60563
Description: Used 2017 Ford F250 Lariat for sale - $56,998, 54,174 miles with Flex Fuel Vehicle, 4WD/AWD, Leather Seats, Satellite Radio Ready, Parking Sensors, Rear View Camera
Transmission: Automatic Color:White Interior Color: Tan Average Vehicle Review: (5 reviews)

2021 Jeep Gladiator Sport

$43,998•15K mi

Free Shipping from CarMax Glencoe (Edens Expy), IL

Key Features
Bed Cover, 4WD/AWD, Satellite Radio Ready, Rear View Camera, Auxiliary Audio Input, Traction Control
Location: CarMax Glencoe (Edens Expy) in Glencoe, Illinois 60022
Description: Used 2021 Jeep Gladiator Sport for sale - $43,998, 14,840 miles with Bed Cover, 4WD/AWD, Satellite Radio Ready, Rear View Camera, Auxiliary Audio Input, Traction Control
Transmission: Automatic Color:Gray Interior Color: Gray Average Vehicle Review: (0 reviews)

2016 Chevrolet Colorado Z71

$31,998•89K mi

Free Shipping from CarMax Schaumburg, IL

Key Features
Bed Cover, 4WD/AWD, BOSE Sound System, Satellite Radio Ready, Rear View Camera, Front Seat Heaters
Location: CarMax Schaumburg in Chicago, Illinois 60173
Description: Used 2016 Chevrolet Colorado Z71 for sale - $31,998, 88,795 miles with Bed Cover, 4WD/AWD, BOSE Sound System, Satellite Radio Ready, Rear View Camera, Front Seat Heaters
Transmission: Automatic Color:Black Interior Color: Gray Average Vehicle Review: (4.625 reviews)

2019 Ram 1500 Laramie

$51,998•68K mi

Available at your store CarMax Hillside (Eisenhower Expy), IL

Key Features
Bed Cover, 4WD/AWD, Leather & Suede Seats, Alpine Sound System, Satellite Radio Ready, Parking Sensors
Location: CarMax Hillside (Eisenhower Expy) in Chicago, Illinois 60162
Description: Used 2019 Ram 1500 Laramie for sale - $51,998, 67,250 miles with Bed Cover, 4WD/AWD, Leather & Suede Seats, Alpine Sound System, Satellite Radio Ready, Parking Sensors
Transmission: Automatic Color:Black Interior Color: Black Average Vehicle Review: (4.818181818181818 reviews)

2014 Ford F150 STX

$37,998•12K mi

Available at your store CarMax Hillside (Eisenhower Expy), IL

Key Features
Flex Fuel Vehicle, 4WD/AWD, Satellite Radio Ready, Rear View Camera, Running Boards, Alloy Wheels
Location: CarMax Hillside (Eisenhower Expy) in Chicago, Illinois 60162
Description: Used 2014 Ford F150 STX for sale - $37,998, 11,297 miles with Flex Fuel Vehicle, 4WD/AWD, Satellite Radio Ready, Rear View Camera, Running Boards, Alloy Wheels
Transmission: Automatic Color:Red Interior Color: Black Average Vehicle Review: (4.509090909090909 reviews)

2016 Ram 1500 Tradesman

$30,998•46K mi

Available at your store CarMax Hillside (Eisenhower Expy), IL

Key Features
Flex Fuel Vehicle, Bed Cover, 4WD/AWD, Running Boards, Alloy Wheels, Auxiliary Audio Input
Location: CarMax Hillside (Eisenhower Expy) in Chicago, Illinois 60162
Description: Used 2016 Ram 1500 Tradesman for sale - $30,998, 45,023 miles with Flex Fuel Vehicle, Bed Cover, 4WD/AWD, Running Boards, Alloy Wheels, Auxiliary Audio Input
Transmission: Automatic Color:Black Interior Color: Gray Average Vehicle Review: (4.8 reviews)

2020 Jeep Gladiator Rubicon

$54,998•16K mi

Free Shipping from CarMax Naperville, IL

Key Features
Cold Weather Package, Bed Cover, 4WD/AWD, Leather Seats, Satellite Radio Ready, Rear View Camera
Location: CarMax Naperville in Naperville, Illinois 60563
Description: Used 2020 Jeep Gladiator Rubicon for sale - $54,998, 15,591 miles with Cold Weather Package, Bed Cover, 4WD/AWD, Leather Seats, Satellite Radio Ready, Rear View Camera
Transmission: Automatic Color:Gray Interior Color: Black Average Vehicle Review: (5 reviews)

2018 Ram 1500 Tradesman

$31,998•8K mi

Free Shipping from CarMax Glencoe (Edens Expy), IL

Key Features
Flex Fuel Vehicle, Rear View Camera, Bed Liner, Auxiliary Audio Input, Overhead Airbags, Traction Control
Location: CarMax Glencoe (Edens Expy) in Glencoe, Illinois 60022
Description: Used 2018 Ram 1500 Tradesman for sale - $31,998, 7,640 miles with Flex Fuel Vehicle, Rear View Camera, Bed Liner, Auxiliary Audio Input, Overhead Airbags, Traction Control
Transmission: Automatic Color:Gray Interior Color: Gray Average Vehicle Review: (4.8125 reviews)

2018 Toyota Tundra SR5

$41,998•46K mi

Free Shipping from CarMax Naperville, IL

Key Features
Flex Fuel Vehicle, Bed Cover, 4WD/AWD, Satellite Radio Ready, Parking Sensors, Rear View Camera
Location: CarMax Naperville in Naperville, Illinois 60563
Description: Used 2018 Toyota Tundra SR5 for sale - $41,998, 45,785 miles with Flex Fuel Vehicle, Bed Cover, 4WD/AWD, Satellite Radio Ready, Parking Sensors, Rear View Camera
Transmission: Automatic Color:Silver Interior Color: Black Average Vehicle Review: (5 reviews)

2020 Jeep Gladiator Sport

$43,998•11K mi

Available at your store CarMax Hillside (Eisenhower Expy), IL

Key Features
Bed Cover, 4WD/AWD, Rear View Camera, Bed Liner, Running Boards, Alloy Wheels
Location: CarMax Hillside (Eisenhower Expy) in Chicago, Illinois 60162
Description: Used 2020 Jeep Gladiator Sport for sale - $43,998, 10,207 miles with Bed Cover, 4WD/AWD, Rear View Camera, Bed Liner, Running Boards, Alloy Wheels
Transmission: Manual 6 Speed Color:Tan Interior Color: Black Average Vehicle Review: (5 reviews)

2014 GMC Sierra 1500 SLE

$35,998•62K mi

Free Shipping from CarMax Schaumburg, IL

Key Features
Flex Fuel Vehicle, Bed Cover, 4WD/AWD, Satellite Radio Ready, Parking Sensors, Rear View Camera
Location: CarMax Schaumburg in Chicago, Illinois 60173
Description: Used 2014 GMC Sierra 1500 SLE for sale - $35,998, 61,989 miles with Flex Fuel Vehicle, Bed Cover, 4WD/AWD, Satellite Radio Ready, Parking Sensors, Rear View Camera
Transmission: Automatic Color:Red Interior Color: Gray Average Vehicle Review: (4.733333333333333 reviews)

2016 GMC Sierra 1500 Denali

$44,998•60K mi

Available at your store CarMax Hillside (Eisenhower Expy), IL

Key Features
Bed Cover, 4WD/AWD, Leather Seats, BOSE Sound System, Satellite Radio Ready, Parking Sensors
Location: CarMax Hillside (Eisenhower Expy) in Chicago, Illinois 60162
Description: Used 2016 GMC Sierra 1500 Denali for sale - $44,998, 59,417 miles with Bed Cover, 4WD/AWD, Leather Seats, BOSE Sound System, Satellite Radio Ready, Parking Sensors
Transmission: Automatic Color:Black Interior Color: Black Average Vehicle Review: (5 reviews)

2021 Toyota Tacoma TRD Off Road

$46,998•8K mi

Free Shipping from CarMax Schaumburg, IL

Key Features
Premium Package, Bed Cover, 4WD/AWD, Satellite Radio Ready, Rear View Camera, Running Boards
Location: CarMax Schaumburg in Chicago, Illinois 60173
Description: Used 2021 Toyota Tacoma TRD Off Road for sale - $46,998, 7,517 miles with Premium Package, Bed Cover, 4WD/AWD, Satellite Radio Ready, Rear View Camera, Running Boards
Transmission: Automatic Color:Gray Interior Color: Gray Average Vehicle Review: (0 reviews)

2019 Ford F150 XLT

$38,998•56K mi

Free Shipping from CarMax Schaumburg, IL

Key Features
4WD/AWD, Rear View Camera, Bed Liner, Alloy Wheels, Auxiliary Audio Input, Overhead Airbags
Location: CarMax Schaumburg in Chicago, Illinois 60173
Description: Used 2019 Ford F150 XLT for sale - $38,998, 55,287 miles with 4WD/AWD, Rear View Camera, Bed Liner, Alloy Wheels, Auxiliary Audio Input, Overhead Airbags
Transmission: Automatic Color:Red Interior Color: Black Average Vehicle Review: (4.4375 reviews)
New Arrival

2017 Ram 1500 Bighorn

$37,998•44K mi

Available at your store CarMax Hillside (Eisenhower Expy), IL

Key Features
Bed Cover, 4WD/AWD, Satellite Radio Ready, Parking Sensors, Rear View Camera, Navigation System
Location: CarMax Hillside (Eisenhower Expy) in Chicago, Illinois 60162
Description: Used 2017 Ram 1500 Bighorn for sale - $37,998, 43,809 miles with Bed Cover, 4WD/AWD, Satellite Radio Ready, Parking Sensors, Rear View Camera, Navigation System
Transmission: Automatic Color:Silver Interior Color: Gray Average Vehicle Review: (4.2631578947368425 reviews)
New Arrival

2022 Toyota Tacoma SR

$32,998•1K mi

Free Shipping from CarMax Naperville, IL

Key Features
Satellite Radio Ready, Rear View Camera, Bed Liner, Auxiliary Audio Input, Overhead Airbags, Traction Control
Location: CarMax Naperville in Naperville, Illinois 60563
Description: Used 2022 Toyota Tacoma SR for sale - $32,998, 392 miles with Satellite Radio Ready, Rear View Camera, Bed Liner, Auxiliary Audio Input, Overhead Airbags, Traction Control
Transmission: Automatic Color:White Interior Color: Gray Average Vehicle Review: (0 reviews)
New Arrival

2018 Ford F150 XLT

$40,998•14K mi

Free Shipping from CarMax Schaumburg, IL

Key Features
Sport Package, Flex Fuel Vehicle, Satellite Radio Ready, Parking Sensors, Rear View Camera, Navigation System
Location: CarMax Schaumburg in Chicago, Illinois 60173
Description: Used 2018 Ford F150 XLT for sale - $40,998, 13,757 miles with Sport Package, Flex Fuel Vehicle, Satellite Radio Ready, Parking Sensors, Rear View Camera, Navigation System
Transmission: Automatic Color:Silver Interior Color: Black Average Vehicle Review: (4.633333333333334 reviews)

2016 Chevrolet Silverado 1500 LT

$35,998•76K mi

Free Shipping from CarMax Schaumburg, IL

Key Features
4WD/AWD, Satellite Radio Ready, Bed Liner, Running Boards, Alloy Wheels, Auxiliary Audio Input
Location: CarMax Schaumburg in Chicago, Illinois 60173
Description: Used 2016 Chevrolet Silverado 1500 LT for sale - $35,998, 75,184 miles with 4WD/AWD, Satellite Radio Ready, Bed Liner, Running Boards, Alloy Wheels, Auxiliary Audio Input
Transmission: Automatic Color:Black Interior Color: Black Average Vehicle Review: (4.666666666666667 reviews)

2020 Ford F150 King Ranch

$62,998•6K mi

Free Shipping from CarMax Glencoe (Edens Expy), IL

Key Features
Technology Package, 4WD/AWD, Turbo Charged Engine, Leather Seats, Satellite Radio Ready, Parking Sensors
Location: CarMax Glencoe (Edens Expy) in Glencoe, Illinois 60022
Description: Used 2020 Ford F150 King Ranch for sale - $62,998, 5,033 miles with Technology Package, 4WD/AWD, Turbo Charged Engine, Leather Seats, Satellite Radio Ready, Parking Sensors
Transmission: Automatic Color:Black Interior Color: Brown Average Vehicle Review: (4.4 reviews)

This price does not include tax, title, and tags. Additional fees may also apply depending on the state of purchase.