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Used
Chevrolet Silverado 1500 Custom Trail Boss
for sale
near
Bolingbrook, IL
- 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.
**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.






Used
2020 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features
Reviews
Great experience with Luis Portales in sales.
Great experience with Luis Portales in sales. Showed us many different cars and options. No pressure to buy. Very easy to talk to and he listened to what we were looking for
I have a 2020 1500 RST with the 5.
I have a 2020 1500 RST with the 5.3 engine and 8 speed transmission. My truck now has 67,000 miles. The acceleration is outstanding and smooth from gears 3-8. Probably could use more torque for gears 1-2, but not weak by any means. I have had no mechanical problems outside of the clunking rear suspension which was fixed by retorqueing the rear leaf spring suspension bolts. Other than that minor issue, it has been very reliable. I have heard these transmissions have had issues, but nothing that has caused issues for me. It has the 60-70 MPH shutter that is common to these transmissions, but I have learned how to drive to avoid the shutter, as I did with my 2011 1500. Overall pretty satisfied at this point. Comfort and amenities could be better for the front seats for the price, but I bought it knowing that. FYI my front brakes at this point are still 50%, and I have invested very little outside of a few fluid exchanges and routine maintenance. Excellent fuel mileage: 20 mpg with 50% highway vs city driving.






Used
2019 Chevrolet Silverado 1500 Custom Trail Boss






Used
2024 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features
Reviews
Very nice dealership experience.
Very nice dealership experience. Jorge was very helpful and knowledgeable during my vehicle purchase. If you plan on purchasing from Toyota of Naperville, Jorge is the salesman to see.
My 2024 Chevy Silverado LTZ provides a deluxe large SUV
My 2024 Chevy Silverado LTZ provides a deluxe large SUV interior and a standard (short) tuck bed all in one vehicle. It is loaded with features to make it look and operate very well, and it provides mid 20's regular unleaded fuel mileage. The dynamic fuel management system combined with the 10 speed automatic transmission work together flawlessly to deliver smooth power without being able to realize what gear or how many cylinders the powertrain is using at any given time.






Used
2024 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features
Reviews
A'Darcy made it worth my time and drive
Service was excellent they were very transparent very very good treatment would highly recommend this dealership. No pressure to buy. If you want good service without the pressure this is the place to go. Thank you very much I really appreciate the service I was given.
What I am most satisfied with is its color.
What I am most satisfied with is its color. This matte silver color is matched with silver wheels, which is really unique. The matte texture is very good, and the personality is low-key but full of connotation. I just like not to follow the crowd.






Used
2021 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
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Reviews
My experience with Lawrence & Ryan at Greenway Auto/GMC
My experience with Lawrence & Ryan at Greenway Auto/GMC was very good. They were very helpful and made my car buying easy. I would recommend Greenway to anyone looking for a new vehicle..
2021 LT Trail Boss has great styling, powerful engines,
2021 LT Trail Boss has great styling, powerful engines, and tons of technology in a great package. A commanding view of the road, a nice comfortable interior, amazing Bose Stereo system, tons of storage and tons of space for adults in the crew cab. But there are issues, side mirrors are too small, harsher ride (which I expected), and DFM, GDI engines, and questions on the 10 speed transmissions. I recommend disabling DFM ASAP or using the L9 trick to overide the system, to help prolong the life of the engines from lifter failure. Mine is under warranty for another 18K miles, if it acts up at all its into the dealership for warranty service.






Used
2021 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features
Reviews
Excellent Service and Response
Thank you for getting my cehicle repairs done and workinf so hard to het me out of there to get to where I needed to go.
Beauty Truck
I drove a '99 Silverado Standard Cab 6 cyl for 24 years & decided it was time. I flirted with Ram & Tundra but when it came down to it, I've got Chevy in my blood & found what I think is a special vehicle. I'm still learning, lots of buttons, bells & whistles but think I'm gonna love this truck. It's big, real big, you have to plan for some driving/parking experiences ahead of time because it can't do what a single cab did. Would have preferred the 5.3 but ended up with a 6.2 but wow, power on demand, this baby moves. No need to worry about passing granny anymore.






Used
2022 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features
Reviews
"Jakub Sales delivers exceptional service, exceeding
"Jakub Sales delivers exceptional service, exceeding expectations with top-notch quality and professionalism. Highly recommended!"
very good truck it is the best car i jave bought since my
very good truck it is the best car i jave bought since my opd one was broken this help me alot and thanks for seeing this






Chevrolet Certified
2023 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
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Reviews
Excellent treatment jorge help alot on purchase of 2025
Excellent treatment jorge help alot on purchase of 2025 car explained every single step gott us a best deal for us thankx again jorge for everything.best dealer had lots of ars too chose
good trk
been buying dhevy trucks since 1976 was my 1st truck, now i got a 2022 silverado with a 6.2 last Feb. of 2023,kicked up the computer kicking out 454 horse power to the wheels, still waiting on my tow mirrors dont make the wiring harrness for my modle is the only problem im having with this truck, will never buy any other truck.






Used
2020 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features
Reviews
Thank you to the service team for your getting me all set
Thank you to the service team for your getting me all set for my roadtrip!
Purchased new a 2020 Chevrolet custom Trail Boss in Satin
Purchased new a 2020 Chevrolet custom Trail Boss in Satin Steel metallic, it has been great. I just turned 80,000 miles with no issues, it’s been a pleasure to drive, just replaced brakes and tires for the first time at 75,000 miles . I have also purchased new a 86 F-250 and a 01 GMC 1500 which also were great trucks and sold with 190,000 miles on them. Maintenance is key Chevrolet did a great job on the exterior of this truck, love the look and color. Nothing bad to say only a positive experience.






Used
2019 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
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Reviews
Schaumburg ford is awesome
This is my Second purchase with them, they have a excellent team and overall great experience with tons of details explained.
Oil line failure
I recently found a oil leak earlier on the engine oil cooling lines. It took a couple of days to find the parts to fix it. It seems the there were 3 dealers in the area that had the part but they were already designated for other pickups with the same problem. This being said I believe GM is aware of the problem and should take responsibility for the cost encured for repairs.






Used
2021 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features
Reviews
Haggerty is great place to buy & service your car
From originally purchasing my car at Haggerty to having my car serviced at Haggerty, my experiences have all been positive. Everyone is friendly and answers all of my questions. Work is done well and on time.
1st truck in 20 years.
My Silverado runs and drives perfectly. My only complaint is the paint job. Every week when I clean the truck I find new nicks in the paint. Almost like there's no primer. I'm concerned about resale value because no matter how careful I am and I'm an older driver, paint is getting worse every day.






Used
2019 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
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Reviews
Always great service!
Always great service!! Very informative on the problem. Always updating on time car will be done. Always knowledgeable on problem. Car always ready when they say it will be.
Will buy another Chevrolet but older.
I have owned Chevrolet for over 70 years but the newer they get the worse the Electricions get right now having trouble with the brakes only work when everything esle is working.






Used
2020 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features
Reviews
Great experience overall , we purchased out of state .
Great experience overall , we purchased out of state . The car came as described ( via facetime )
So far so good. Its not a Dodge or Ford
Best truck I've ever owned. Great power...good fule economy on highways. comfortable and roomy great bose sound system No over dramatic fanciness but practicality. I like the design and added features such as a sliding rear window power outlets inside and in the bed. 20k miles on her so...maybe too soon to tell?






Used
2020 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features
Reviews
buena atención Joel Hernández muy amable y calidad en
buena atención Joel Hernández muy amable y calidad en servicio y rapidez en su trabajo
CHEVROLET Silverado 4 cylinder turbo charged engin
Awesome Truck except for transmission troubles. Very good gas mileage and comfort and ride are the best. A very dependable truck with lots of great features. Back up camera is great.






Used
2024 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features
Reviews
The process was easy.
The process was easy. Went to see the car but they were waiting for a part. We liked it right away. When it was finished they called us to test drive. Dan and Dave were terrific no pressure. They gave us a figure and we gave them ours and they did more than we asked for including accessories. John in finance and John the gm were also terrific. I rate this dealership very high.
Purchased new vehicle at Hendrix Chevrolet, Charlotte,
Purchased new vehicle at Hendrix Chevrolet, Charlotte, North Carolina helped by Chadwick, Dana, Brandon,& Nicholas, great hospitality great service. Excellent experience word buy her again






Used
2024 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features
Reviews
Very professional and courteous sales staff.
Very professional and courteous sales staff. Some behind the scenes issues with info I'd received by email being incorrect, but it was solved quick enough.
For context, I don’t buy new vehicles often.
For context, I don’t buy new vehicles often. My last truck was a 2002 Chevy Silverado 1500 LS. I drove it 22 years and put over 200,000 miles on it. It was a great truck, so I wanted to replace it with another one. In late November, I purchased a 2024 Silverado 1500 LTZ with all the bells and whistles and I couldn’t be happier with a vehicle. It looks fantastic, Summit White, crew cab with short bed and 20” wheels have it sitting at the perfect height. Inside there is plenty of headroom for 6 ft plus people. The seats are super comfortable and it drives and rides fabulously. The interior is amazing. My wife, who generally doesn’t care much for trucks raves about it every time she sits in it. She says she can’t believe how comfortable it is and wants to take trips in it. If there is anything I have to say that is a bit negative is how the 10 speed transmission works at slow speeds. At times, I experience a sort of surging with it. The truck apparently “learns” your driving habits, so that may have something to do with it. Otherwise, I really enjoy everything about it. Looking for another 20 years with it!:)






Used
2024 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
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Reviews
An Outstanding Car Buying Experience at South Oak Dodge
An Outstanding Car Buying Experience at South Oak Dodge Chrysler Jeep Ram of Matteson, IL Our recent car buying experience at South Oak of Matteson, IL was nothing short of incredible, thanks to the exceptional help and expertise of Ryan Ganser, the Finance Manager, and Aaron Mathews, our Sales Professional. From the moment we walked in, Ryan and Aaron created a warm and welcoming environment. Their knowledge and informative approach made us feel confident and well-guided throughout the entire process. Ryan's financial expertise ensured everything was seamless, while Aaron's professionalism and personable manner made us feel valued as customers. We left with not just a vehicle we love, but also the joy of knowing we made the right choice with South Oak. We would highly recommend Aaron Mathews and Ryan Ganser to anyone in the market for purchasing a vehicle—they truly set the standard for customer service and excellence.
I own a 2024 2WD WT, Double Cab.
I own a 2024 2WD WT, Double Cab. The WT model is the least expensive of the line up and comes with the 2.7L 4-cylinder HO motor. It has analog gauges, which I actually prefer over LED displays. The engine pulls like a V8 and sounds more like a small diesel. The 8 speed transmission shifts at the right times and is smooth. Cabin noise is minimal. It is a solid truck!






Used
2021 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
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Reviews
Great place to buy a vehicle.
Great place to buy a vehicle. The staff is very friendly and the process was very easy
Great Truck
Ive driven 43,000 miles. Runs and drives great. Love the 10 spd transmission for towing. Only issue was a faulty clock spring for heated steer wheel. Under warranty. Has the 6.2 ltr motor






Used
2019 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features
Reviews
Very good profesional Menager Kris and all staff very
Very good profesional Menager Kris and all staff very helpful . They stay with me even after the hours and show me all of the cars I wanna see! So definitely I will recommend this dealership to all of my friends. Thank you again.
Awesome!!!
I took my Chevy Silverado in for a check engine light with no appointment and Melvin Thomas III greeted me and documented my concerns to have my vehicle inspected. Retrieved my vehicle the same day with all concerns addressed. I will definitely return to see my new advisor Mr. Melvin.






Used
2025 Chevrolet Silverado 1500 Custom Trail Boss
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Reviews
Great professional knowledgeable Customer Service!
Matt, Azbel were top with great first impression, and even better lasting impression! Great Service also from Moshe, Jeremy, Tino, Tamu, and welcoming crew. I am happy with my beautiful and spotless new car and dealership is the same. Friendly and very knowledgeable crew! I send everyone there for a great car, caring and trustworthy staff who will help you select the vehicle that's right for you!
Love this car.
Love this car. I wish there was more to the interior though, as it is pretty plain and nothing extraordinary. If they had the bigger infotainment screen for the front bench seat it would have a gotten that one. This car over all is great bang for the buck.






Used
2023 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features
Reviews
Kris Kevorkian was such a great sales and got us a great
Kris Kevorkian was such a great sales and got us a great deal on a new car.
Workhorse of a truck
This is my 3rd Silverado and the best one yet. The infotainment features are great. The screen is big and easy to work. Looks great, rides smooth, quiet and is plenty powerful. (5.3 V8) Great every day driver for my family of 4.
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*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.
Chevrolet Silverado 1500 Custom Trail Boss by city
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2 Great Deals out of 20 listings starting at $19,945
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2 Great Deals out of 28 listings starting at $19,945
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1 Great Deal out of 20 listings starting at $19,945
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2 Great Deals out of 28 listings starting at $19,945
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2 Great Deals out of 28 listings starting at $19,945
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2 Great Deals out of 20 listings starting at $19,945
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21 listings starting at $46,945
Chevrolet Silverado 1500 by trim
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Chevrolet Silverado 1500 LT
11 Great Deals out of 103 listings starting at $6,950
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4 Great Deals out of 64 listings starting at $25,999
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Chevrolet Silverado 1500 LT Trail Boss
4 Great Deals out of 39 listings starting at $26,700
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4 Great Deals out of 38 listings starting at $9,995
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5 Great Deals out of 22 listings starting at $10,988
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This vehicle is certified pre-owned, backed by a manufacturer warranty, and typically undergoes a rigorous multi-point inspection to ensure quality and reliability.
This vehicle is currently in high demand given its competitive price, desirable features, and overall condition, and may have a higher chance of selling quickly.