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Used
Chevrolet Silverado 1500 Custom Trail Boss
for sale
near
Winfield, 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
2024 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features
Reviews
Had a great experience with Steve D.
Had a great experience with Steve D. Very knowledgeable and honest. The process was easy and smooth,and would return for my next purchase. Would recommend to anyone.
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
2025 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features
Reviews
Let me just start off by saying.
Let me just start off by saying.....I have never met a more patient man/salesman than MOSHI!!!! This was my first ever car buying experience at a dealership and the anxiety was real. But no one else I would have rather had as a product specialist, than Moshi. Words cannot even begin to express my appreciation for his services. He was very punctual, professional, transparent, understanding and genuinely made the entire experience as comfortable as possible. Not to mention, he's very knowledgeable when it comes to vehicle systems. As difficult as I was as a first-time buyer, I commend Moshi for patiently working with me on site of the dealership, for hours, without giving up until I was comfortable enough with signing and driving my car off the lot. His dedication truly paid off because I couldn't be happier with my purchase. I arrived pre-approved for a loan and left with a better rate after their finance dept. hooked it up. Even after my purchase, Moshi checked in to see how I was doing with my purchase. Truly cannot express how thankful I am to everyone at this dealership for taking the time to work with me and easing my anxiousness with the process. Seriously though, promote a brotha! Moshi was the best!! Highly recommend working with him if you're looking to buy your next vehicle! Thank you to everyone at this dealership for your efforts. I'm forever grateful for my Mazda CX-5!!
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
Webb Chevy is the only place I will service my vehicle
Webb Chevy is the only place I will service my vehicle at, they are the best on the Southside!
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
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.
Thumbs up
Since I've owned it, so far so good. I like my truck and I appreciate it everyday. A little bit of shaking in the steering at high speeds but I'm not concerned with it. Overall, pretty great.






Used
2023 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features
Reviews
The service and the sales department are too notch!
The service and the sales department are too notch!! Highly recommend!! I won’t good to any other dealer
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.






Used
2019 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features
Reviews
Great service.
Great service. The service department was courteous and friendly. My car was serviced and ready to go in a reasonable amount of time. I was very satisfied.
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
2019 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features
Reviews
Another great trip to A Phillips Chevy!
Another great trip to A Phillips Chevy!! Fast service, clean shop, friendly service staff. Been buying from Phillips since 2002. Will be back soon, Thank you
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
Everyone i dealt with at the dealership was very
Everyone i dealt with at the dealership was very welcoming. They were also quick and efficient getting me into my new vehicle.
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.






Chevrolet Certified
2023 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features
Reviews
I felt with Jorge Rodrigues who I believe is a very
I felt with Jorge Rodrigues who I believe is a very competent sales person who went above and beyond to locate the vehicle I wanted and after the sale was completed has followed up with 1st class information on the EV systems. Just wish you had more than 5 stars as 5 isn?t enough to rate Jorge Rodrigues who is an outstanding sales person at Sunrise Chevrolet.
Great truck
Great truck awesome power Has the usual infotainment system issues that all makes have the sound goes out and radio system locks up shut it down for a few then works again The steering column upper cover came a part when I picked it up the dealer ordered the part but it’s been 3 months no called from the dealer ( Unity Chevy ) Newburgh ny No status updates very poor dealer Also no fog lights and none are available from the dealer or after market needs fog lights the normal headlights just aren’t enough lighting for night driving One other note the antenna paint is peeling and the dealer said I had to pay for that Lol truck had 230 miles on it the dealer was a joke so I will be going to another dealer for and warranty work






Used
2019 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features
Reviews
I completed my deal in less then 2 hours , gave me good
I completed my deal in less then 2 hours , gave me good money for my trade and a deal on the new one.
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
2021 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features
Reviews
Very professional, excellent communication Friendly
Very professional, excellent communication Friendly staff, and had the vehicle we wanted, would deal with them again
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
2024 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features
Reviews
Great experience, Patrycja (our sales associate) was
Great experience, Patrycja (our sales associate) was great. We purchased a 2023 Tesla model Y
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
2020 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features
Reviews
recently purchased a vehicle from Old Orchard Nissan, and
recently purchased a vehicle from Old Orchard Nissan, and I couldn’t be more satisfied with the entire experience. From the moment I walked in, the staff was welcoming, professional, and genuinely helpful — no pressure, just honest service. My salesperson, Jason Chu, was knowledgeable, patient, and took the time to answer all my questions. They helped me find the perfect car for my needs and made the process feel smooth and stress-free. The finance team also did a great job explaining everything clearly and worked to get me a great deal. The vehicle was clean, in excellent condition, and exactly as described. I truly appreciate the transparency, integrity, and care that went into every step of the process. Highly recommend Old Orchard Nissan to anyone looking for a reliable vehicle and top-notch customer service. I’ll definitely be back when it’s time for my next car!
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
2020 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features
Reviews
Loved my experience at Top Gear Motors, such an easy
Loved my experience at Top Gear Motors, such an easy process and car was pristine. Will definitely come for all future purchases and recommend others do the same.
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
The service met what i needed.
The service met what i needed. I was able to ensure that the price of the repairs that were needed were affordable and correct. I just wish some of the future repairs that are needed are more affordable and could be more explained by the customer service representative like the previous rep that I had at the previous visit. Overall, the facility was very clean and i was able to meet with one of the car/service representative. I was able to meet with a car dealer who was very friendly and ensure that I had his contact information, in the event I plan or may want to purchase a new vehicle in the near future, which i plan too.
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
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Reviews
Matt is sales was very open and honest.
Matt is sales was very open and honest. He worked to get the payment I needed!
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
2020 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features
Reviews
I have brought my vehicle in for every oil change I have
I have brought my vehicle in for every oil change I have needed. Always courteous and professional, my car gets a diagnostic check every time and is freshly washed. I like that the Service Department send out coupons, and making an appointment is easy online or with a phone call.
Good basic pickup
Have had this since new in 2020. No major issues. Transmission is rough when cold, but not an issue. Three years in and no major work. One brake adjustment and oil changes. Other than that it’s been a great truck.






Used
2020 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features
Reviews
Great place to buy a vehicle.
Great place to buy a vehicle. The staff is very friendly and the process was very easy






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.
#1 Chevy Silverado
Not surprised the Chevrolet Silverado was named #1 Best Truck!! Overall, I highly recommend driving and owning a Silverado! From the way it drives to the technology with safety and convenience features, the Silverado is a solid choice.






Chevrolet Certified
2022 Chevrolet Silverado 1500 Custom Trail Boss
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Reviews
My salesman victor was great.
My salesman victor was great. The process was quick. I did not have to wait hours like at other dealerships I would definitely recommend you check Mike Anderson Chevrolet out. Thanks for everything
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
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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
-
Chevrolet Silverado 1500 Custom Trail Boss in Wheaton, IL
1 Great Deal out of 30 listings starting at $19,945
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Chevrolet Silverado 1500 Custom Trail Boss in Carol Stream, IL
1 Great Deal out of 29 listings starting at $19,945
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Chevrolet Silverado 1500 Custom Trail Boss in West Chicago, IL
1 Great Deal out of 29 listings starting at $19,945
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1 Great Deal out of 30 listings starting at $19,945
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Chevrolet Silverado 1500 Custom Trail Boss in Glen Ellyn, IL
1 Great Deal out of 30 listings starting at $19,945
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Chevrolet Silverado 1500 Custom Trail Boss in Glendale Heights, IL
1 Great Deal out of 29 listings starting at $19,945
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Chevrolet Silverado 1500 Custom Trail Boss in Bloomingdale, IL
1 Great Deal out of 29 listings starting at $19,945
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Chevrolet Silverado 1500 Custom Trail Boss in Lisle, IL
1 Great Deal out of 30 listings starting at $19,945
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Chevrolet Silverado 1500 Custom Trail Boss in Lombard, IL
1 Great Deal out of 31 listings starting at $19,945
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Chevrolet Silverado 1500 Custom Trail Boss in Hanover Park, IL
1 Great Deal out of 29 listings starting at $19,945
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Chevrolet Silverado 1500 Custom Trail Boss in Wayne, IL
1 Great Deal out of 24 listings starting at $19,945
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Chevrolet Silverado 1500 Custom Trail Boss in Bartlett, IL
1 Great Deal out of 24 listings starting at $19,945
Chevrolet Silverado 1500 by trim
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Chevrolet Silverado 1500 LT
13 Great Deals out of 90 listings starting at $6,950
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Chevrolet Silverado 1500 RST
6 Great Deals out of 62 listings starting at $25,999
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Chevrolet Silverado 1500 LTZ
10 Great Deals out of 57 listings starting at $4,995
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Chevrolet Silverado 1500 LT Trail Boss
5 Great Deals out of 37 listings starting at $26,770
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Chevrolet Silverado 1500 1LT
9 Great Deals out of 29 listings starting at $12,995
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Chevrolet Silverado 1500 Custom
2 Great Deals out of 28 listings starting at $18,999
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Chevrolet Silverado 1500 WT
5 Great Deals out of 23 listings starting at $10,988
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Chevrolet Silverado 1500 High Country
3 Great Deals out of 22 listings starting at $17,945
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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.