Pickup Trucks For Sale near Chicago, IL

Commercial Truck Sales has new and used pickup trucks for sale from leading manufacturers. Find what you need and connect directly to dealers.

Pickup trucks near Chicago, IL: 472 listings within 50 miles from 34 dealers. Prices range from $3,000 to $230,137. Average mileage is 31,929 miles. Top makes: Ford, Ram and Chevrolet.

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472 matches

$98,635

2026 GMC Sierra 2500 HD Denali Ultimate

Chicago, IL (2.1 mi)

2026 GMC Sierra 2500 HD Denali Ultimate

Pickup

Diesel · 4WD

Experience the 2026 GMC Sierra 2500 HD at Napleton Downtown Chevrolet - a versatile pickup blending power, comfort, and innovation. Schedule your test drive today.

Stock #: 1GT4UXEY4TF358846

$98,635

2.1 mi away

Chicago, IL

$80,450

2026 GMC Sierra 1500 Denali

Chicago, IL (2.1 mi)

2026 GMC Sierra 1500 Denali

Pickup

Gasoline · 4WD

Experience the 2026 GMC Sierra 1500 at Napleton Downtown Chevrolet - a versatile pickup blending power, comfort, and innovation. Schedule your test drive today.

Stock #: 1GTUUGEL9TZ330821

$80,450

2.1 mi away

Chicago, IL

2026 Chevrolet Silverado 2500 HD - Pickup

$79,785

2026 Chevrolet Silverado 2500 HD LT

Chicago, IL (2.1 mi)

2026 Chevrolet Silverado 2500 HD LT

Pickup

Diesel · 4WD

Experience the 2026 Chevrolet Silverado 2500 HD at Napleton Downtown Chevrolet - a versatile pickup blending power, comfort, and innovation. Schedule your test drive today.

Stock #: 1GC4KNEY2TF393606

$79,785

2.1 mi away

Chicago, IL

$79,570

2026 GMC Sierra 2500 HD AT4

Chicago, IL (2.1 mi)

2026 GMC Sierra 2500 HD AT4

Pickup

Gasoline · 4WD

Experience the 2026 GMC Sierra 2500 HD at Napleton Downtown Chevrolet - a versatile pickup blending power, comfort, and innovation. Schedule your test drive today.

Stock #: 1GT4UPE70TF367843

$79,570

2.1 mi away

Chicago, IL

$79,025

2026 GMC Sierra 2500 HD AT4

Chicago, IL (2.1 mi)

2026 GMC Sierra 2500 HD AT4

Pickup

Gasoline · 4WD

Experience the 2026 GMC Sierra 2500 HD at Napleton Downtown Chevrolet - a versatile pickup blending power, comfort, and innovation. Schedule your test drive today.

Stock #: 1GT4UPE7XTF405448

$79,025

2.1 mi away

Chicago, IL

$74,960

2026 GMC Sierra 1500 Denali

Chicago, IL (2.1 mi)

2026 GMC Sierra 1500 Denali

Pickup

Gasoline · 4WD

Experience the 2026 GMC Sierra 1500 at Napleton Downtown Chevrolet - a versatile pickup blending power, comfort, and innovation. Schedule your test drive today.

Stock #: 3GTUUGED7TG287959

$74,960

2.1 mi away

Chicago, IL

$66,850

2026 Chevrolet Silverado 2500 HD LT

Chicago, IL (2.1 mi)

2026 Chevrolet Silverado 2500 HD LT

Pickup

Gasoline · 4WD

Experience the 2026 Chevrolet Silverado 2500 HD at Napleton Downtown Chevrolet - a versatile pickup blending power, comfort, and innovation. Schedule your test drive today.

Stock #: 1GC4KNE72TF347149

$66,850

2.1 mi away

Chicago, IL

$63,865

2026 Chevrolet Silverado 2500 HD LT

Chicago, IL (2.1 mi)

2026 Chevrolet Silverado 2500 HD LT

Pickup

Gasoline · 4WD

Experience the 2026 Chevrolet Silverado 2500 HD at Napleton Downtown Chevrolet - a versatile pickup blending power, comfort, and innovation. Schedule your test drive today.

Stock #: 1GC4KNE77TF347342

$63,865

2.1 mi away

Chicago, IL

$63,470

2026 Chevrolet Silverado 2500 HD LT

Chicago, IL (2.1 mi)

2026 Chevrolet Silverado 2500 HD LT

Pickup

Gasoline · 4WD

Experience the 2026 Chevrolet Silverado 2500 HD at Napleton Downtown Chevrolet - a versatile pickup blending power, comfort, and innovation. Schedule your test drive today.

Stock #: 1GC4KNE71TF350818

$63,470

2.1 mi away

Chicago, IL

$49,645

2026 Chevrolet Silverado 1500 Custom

Chicago, IL (2.1 mi)

2026 Chevrolet Silverado 1500 Custom

Pickup

Gasoline · 4WD

Experience the 2026 Chevrolet Silverado 1500 at Napleton Downtown Chevrolet - a versatile pickup blending power, comfort, and innovation. Schedule your test drive today.

Stock #: 1GCPKBEK9TZ100872

$49,645

2.1 mi away

Chicago, IL

$44,895

2024 Chevrolet Silverado 1500 ZR2

85,900 mi.

Chicago, IL (2.1 mi)

2024 Chevrolet Silverado 1500 ZR2

Pickup

Diesel · 4WD

Experience the 2024 Chevrolet Silverado 1500 at Napleton Downtown Chevrolet - a versatile pickup blending power, comfort, and innovation. Schedule your test drive today.

Stock #: 3GCUDHE80RG141369

$44,895

85,900 mi

2.1 mi away

Chicago, IL

$27,395

2021 Chevrolet Silverado 1500 Custom

64,100 mi.

Chicago, IL (2.1 mi)

2021 Chevrolet Silverado 1500 Custom

Pickup

Gasoline · 4WD

Experience the 2021 Chevrolet Silverado 1500 at Napleton Downtown Chevrolet - a versatile pickup blending power, comfort, and innovation. Schedule your test drive today.

Stock #: 1GCRYBEH2MZ195806

$27,395

64,100 mi

2.1 mi away

Chicago, IL

No Price Listed

2026 Chevrolet Silverado 1500 High Country

Chicago, IL (2.1 mi)

2026 Chevrolet Silverado 1500 High Country

Pickup

Gasoline · 4WD

Experience the 2026 Chevrolet Silverado 1500 at Napleton Downtown Chevrolet - a versatile pickup blending power, comfort, and innovation. Schedule your test drive today.

Stock #: 1GCUKJEL3TZ516499

No Price Listed

2.1 mi away

Chicago, IL

$44,995

2022 GMC Sierra 1500

35,740 mi.

Chicago, IL (3.4 mi)

2022 GMC Sierra 1500

Pickup

Gasoline · 4WD

Blue 2022 GMC Sierra 1500 with Black interior for sale in Chicago. Shop High Quality Auto Group for great deals on all our GMC inventory.

Stock #: 3GTU9CED0NG189949

$44,995

35,740 mi

3.4 mi away

Chicago, IL

2019 Ford F-150 Raptor SuperCrew - Pickup

$41,995

2019 Ford F-150 Raptor SuperCrew 4WD

83,890 mi.

Chicago, IL (3.4 mi)

2019 Ford F-150 Raptor SuperCrew 4WD

Pickup

Automatic, 10-speed · Gasoline · 4WD

Black 2019 Ford F-150 Raptor SuperCrew 4WD with Black interior for sale in Chicago. Shop High Quality Auto Group for great deals on all our Ford inventory.

Stock #: 1FTFW1RG7KFB42070

$41,995

83,890 mi

3.4 mi away

Chicago, IL

2021 GMC Sierra 1500 Elevation Crew Cab - Pickup

$41,995

2021 GMC Sierra 1500 Elevation Crew Cab 4WD

70,179 mi.

Chicago, IL (3.4 mi)

2021 GMC Sierra 1500 Elevation Crew Cab 4WD

Pickup

Gasoline · 4WD

Red 2021 GMC Sierra 1500 Elevation Crew Cab 4WD with Black interior for sale in Chicago. Shop High Quality Auto Group for great deals on all our GMC inventory.

Stock #: 3GTU9CED5MG137036

$41,995

70,179 mi

3.4 mi away

Chicago, IL

2024 Chevrolet Silverado 1500 LT-L Crew Cab - Pickup

$37,995

2024 Chevrolet Silverado 1500 LT-L Crew Cab 4WD

29,475 mi.

Chicago, IL (3.4 mi)

2024 Chevrolet Silverado 1500 LT-L Crew Cab 4WD

Pickup

Gasoline · 4WD

Black 2024 Chevrolet Silverado 1500 LT-L Crew Cab 4WD with Black interior for sale in Chicago. Shop High Quality Auto Group for great deals on all our Chevrolet inventory.

Stock #: 3GCPDKEK4RG449389

$37,995

29,475 mi

3.4 mi away

Chicago, IL

$35,995

2023 Ford F-150 XLT 5.5-ft Bed 4WD

19,643 mi.

Chicago, IL (3.4 mi)

2023 Ford F-150 XLT 5.5-ft Bed 4WD

Pickup

Automatic, 10-speed · Gasoline · 4WD

Red 2023 Ford F-150 XLT 5.5-ft. Bed 4WD with Black interior for sale in Chicago. Shop High Quality Auto Group for great deals on all our Ford inventory.

Stock #: 1FTEW1EP0PKD65003

$35,995

19,643 mi

3.4 mi away

Chicago, IL

2023 Chevrolet Silverado 1500 LT Crew Cab - Pickup

$33,995

2023 Chevrolet Silverado 1500 LT Crew Cab 4WD

28,266 mi.

Chicago, IL (3.4 mi)

2023 Chevrolet Silverado 1500 LT Crew Cab 4WD

Pickup

Gasoline · 4WD

Gray 2023 Chevrolet Silverado 1500 LT Crew Cab 4WD with Black interior for sale in Chicago. Shop High Quality Auto Group for great deals on all our Chevrolet inventory.

Stock #: 1GCPDKEK1PZ288416

$33,995

28,266 mi

3.4 mi away

Chicago, IL

2018 Ram 2500 Tradesman Crew Cab LWB - Pickup

$32,995

2018 Ram 2500 Tradesman Crew Cab LWB 4WD

130,081 mi.

Chicago, IL (3.4 mi)

2018 Ram 2500 Tradesman Crew Cab LWB 4WD

Pickup

Diesel · 4WD

Red 2018 RAM 2500 Tradesman Crew Cab LWB 4WD with Gray interior for sale in Chicago. Shop High Quality Auto Group for great deals on all our RAM inventory.

Stock #: 3C6UR5HL3JG396383

$32,995

130,081 mi

3.4 mi away

Chicago, IL

$32,995

2023 Chevrolet Silverado 1500 LT Crew Cab 4WD

66,633 mi.

Chicago, IL (3.4 mi)

2023 Chevrolet Silverado 1500 LT Crew Cab 4WD

Pickup

Gasoline · 4WD

Brown 2023 Chevrolet Silverado 1500 LT Crew Cab 4WD with Black interior for sale in Chicago. Shop High Quality Auto Sales for great deals on all our Chevrolet inventory.

Stock #: 1GCPDKEK6PZ226137

$32,995

66,633 mi

3.4 mi away

Chicago, IL

2020 Chevrolet Silverado 1500 LTZ Crew Cab Long - Pickup

$31,995

2020 Chevrolet Silverado 1500 LTZ Crew Cab Long Box 4WD

109,186 mi.

Chicago, IL (3.4 mi)

2020 Chevrolet Silverado 1500 LTZ Crew Cab Long Box 4WD

Pickup

Automatic, 8-speed · Gasoline · 4WD

Gray 2020 Chevrolet Silverado 1500 LTZ Crew Cab Long Box 4WD with Black interior for sale in Chicago. Shop High Quality Auto Group for great deals on all our Chevrolet inventory.

Stock #: 1GCUYGEL2LZ134241

$31,995

109,186 mi

3.4 mi away

Chicago, IL

$29,995

2023 Chevrolet Silverado 1500 LT Crew Cab 4WD

122,781 mi.

Chicago, IL (3.4 mi)

2023 Chevrolet Silverado 1500 LT Crew Cab 4WD

Pickup

Gasoline · 4WD

White 2023 Chevrolet Silverado 1500 LT Crew Cab 4WD with Black interior for sale in Chicago. Shop High Quality Auto Sales for great deals on all our Chevrolet inventory.

Stock #: 2GCUDDED7P1109885

$29,995

122,781 mi

3.4 mi away

Chicago, IL

$25,276

2011 Ford F-550 Chassis

110,161 mi.

Chicago, IL (3.4 mi)

2011 Ford F-550 Chassis

Pickup

Automatic · Diesel · 4WD

XL, 2D Standard Cab, Power Stroke 6.7L V8 DI 32V OHV Turbodiesel, TorqShift 6-Speed Automatic with Overdrive, 4WD, Oxford White, Steel Vinyl, ABS brakes, Traction control.<br><br>OUR INTERNET VALUE PRICING MISSION AT MIDWAY DODGE IS TO PRESENT VALUE

Stock #: 1FDUF5HT1BEC88284

$25,276

110,161 mi

3.4 mi away

Chicago, IL

1–24 of 472 results

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Search our inventory. We provide access to new and used pickup trucks from leading manufacturers like Ford, Chevrolet, RAM, GMC, and Toyota. Filter your search by manufacturer, mileage, year, cab type, and other criteria. Whether you need a 1/2 ton for lighter duties, a 3/4 ton for medium loads, or a 1-ton truck for maximum capability, we have options for every job requirement. If you need a vehicle more specialized to your business, check out our service trucks.
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Commercial Truck Sales has pickup trucks for any application. From job site workhorses to fleet vehicles, we connect you with dealers offering new models with the latest technology and quality used trucks at competitive prices.

Ready to Power Your Business? Find Your Pickup Today

Our marketplace brings together serious buyers and reputable dealers without the typical online shopping headaches. Find your truck, connect with the seller, and handle the details your way. Browse our extensive inventory to discover pickups across all major brands and configurations. If you have questions, our comprehensive FAQ has you covered.

Pickup Trucks For Sale near Chicago, IL

Powerful Pickups. Direct Connections. Better Deals.

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Pickup Trucks For Sale near Chicago, IL

Powerful Pickups. Direct Connections. Better Deals.

How it works:

Ready to Power Your Business? Find Your Pickup Today

Nearby cities

More truck types in Chicago, IL

Popular makes in Chicago, IL