Save your search and get notified when new inventory arrives.
Contact seller
Customize your budget
*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.
About your privacy: Cars.com is asking for your ZIP and credit rating because it helps us to make an educated guess at your sales tax and loan interest. These two factors can greatly change your monthly payment.
Used
Chevrolet Silverado 1500 Custom Trail Boss
for sale
near
Wheeling, 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
2019 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features
Reviews
These guys are the very best at what they do, very
These guys are the very best at what they do, very efficient with duty at hand. That means you are in the best hands! Go get your car, make your dream a reality.
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
2021 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features
Reviews
How Great Antioch Chrysler Dodge Jeep Ram Is
Everyone at this Dealership treated me with respect and courtesy. They were all polite and answered my question honestly. Treated me like an adult, not a senile old lady because I have white. Thank you all at Antioch Chrysler Dodge Jeep Ram.
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
2019 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features
Reviews
The entire experience was great!
The entire experience was great! Everyone was friendly and there was a good selection. Randy was excellent to work with. Woodstock Chevy is a great place to buy a vehicle!
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
2022 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features
Reviews
This dealer had the used car I was looking for.
This dealer had the used car I was looking for. The car had the right mileage and a clean fax. The dealership was 1 hour 20 minutes away from me heavy traffic all the way. I figured I would call and ask about the car anyway but I wasn’t planning to drive there. I talked to Phil, a sales rep, and what a gentleman he was. He told me the car was a trade-in and was in fantastic condition. Well, he talked me into driving down there. I arrived about 10 in the morning and left with my new used car by 1:30 that afternoon. I walked Phil through my 128 point inspection, 2 test drives and I ending up looking under the car for any problems. I could not find anything wrong. The car was in great condition just as Phil had described. Phil was a perfect gentleman through the whole process. Every dealership employee I encountered could not do enough for me. Great experience - great car! 6 star experience!
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






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
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
This was the best purchasing experiences I have ever had.
This was the best purchasing experiences I have ever had. The staff were friendly and very helpful. The vehicle was as advertised. Sometimes pictures don't accurately depict the vehicle, not in this case. I would highly recommend CAW to anyone looking to purchase a quality vehicle and be treated like an MVP!
Cab noise
Love my 22 Chevy LTZ truck, I have the cat back mufflers on it which are not that loud. The inside cab noise is really loud from the road noise and pipes. Don't feel the cab is insulated very well.






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.
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
Vehicle information
Features
Reviews
A dealership you can trust
I was looking for a specific car that was at this CarMax. Problem was that I live in Minnesota, not Chicago and would have to traveling a great distance for a car I had not seen other than in pics, potentially risking wasting a great deal of time and money. I had to trust Jonathan, my salesman, to tell me the condition of the car where the pics could not. He was completely honest and the car was exactly what he said it was. Between Jonathan and Adam, the sales manager i was able to close the deal and drive back to home within an hour. I am completely pleased with the car and 100% satisfied with the dealership. I guess you can trust a car dealership. I did and they did not let me down. Thanks guys.
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
we purchased a Subaru here !
we purchased a Subaru here ! we went in and out under an hour !!! would recommend them !
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
Features
Reviews
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
Recently got my dream car here with the help of Bobby
Recently got my dream car here with the help of Bobby Mengler. He went above and beyond making sure everything was perfect and answered all my questions in full details. I definitely recommend this place and most importantly I recommend Bobby. He is amazing!!
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
2020 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!
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
2023 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.
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
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.
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.






Chevrolet Certified
2022 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features
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
Air conditioner failed two times, brought back
Having issues with the AC not working properly, had in 2xs for this an dealerships fines nothing wrong, tells me if it happens again bring back in.






Used
2019 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
Roomy and powerful
Have the custom crew 5.3 .only wish it had center storage and volume controls.these should be standard on a 40 thousand dollar truck.great family truck ,great for pulling and bed hauling.






Used
2020 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features
Reviews
I had a great experience at Old Orchard Nissan.
I had a great experience at Old Orchard Nissan. Antoni was very knowledgeable and helped me and my family with new Nissan rogue. Couldn't be happier with my purchase. I also get a better deal than i expected. Will be telling my friends and family about Antoni.
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
2021 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.
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
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.






Used
2024 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features
Reviews
A salesman named Ron Assaf helped me.
A salesman named Ron Assaf helped me. I was looking for a used Car and I didn’t see the color I wanted so Ron asked me had I considered buying a new vehicle so he showed me a new Car and I walked out of that dealership with a new Car. Thanks Ron for all your help and service you gave me. You were Great.
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.
-
Prev - 1
- 2
-
Next
*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 Prospect Heights, IL
2 Great Deals out of 27 listings starting at $21,945
-
Chevrolet Silverado 1500 Custom Trail Boss in Buffalo Grove, IL
2 Great Deals out of 22 listings starting at $21,945
-
Chevrolet Silverado 1500 Custom Trail Boss in Riverwoods, IL
2 Great Deals out of 21 listings starting at $21,945
-
Chevrolet Silverado 1500 Custom Trail Boss in Arlington Heights, IL
2 Great Deals out of 27 listings starting at $21,945
-
Chevrolet Silverado 1500 Custom Trail Boss in Deerfield, IL
2 Great Deals out of 20 listings starting at $21,945
-
Chevrolet Silverado 1500 Custom Trail Boss in Lincolnshire, IL
2 Great Deals out of 21 listings starting at $21,945
-
Chevrolet Silverado 1500 Custom Trail Boss in Northbrook, IL
2 Great Deals out of 24 listings starting at $21,945
-
Chevrolet Silverado 1500 Custom Trail Boss in Mount Prospect, IL
2 Great Deals out of 27 listings starting at $21,945
-
Chevrolet Silverado 1500 Custom Trail Boss in Bannockburn, IL
2 Great Deals out of 21 listings starting at $21,945
-
Chevrolet Silverado 1500 Custom Trail Boss in Palatine, IL
2 Great Deals out of 23 listings starting at $21,945
-
Chevrolet Silverado 1500 Custom Trail Boss in Long Grove, IL
2 Great Deals out of 21 listings starting at $21,945
-
Chevrolet Silverado 1500 Custom Trail Boss in Glenview, IL
2 Great Deals out of 25 listings starting at $21,945
Chevrolet Silverado 1500 by trim
-
Chevrolet Silverado 1500 LT
19 Great Deals out of 102 listings starting at $3,999
-
Chevrolet Silverado 1500 RST
6 Great Deals out of 59 listings starting at $26,887
-
Chevrolet Silverado 1500 LTZ
5 Great Deals out of 39 listings starting at $4,995
-
Chevrolet Silverado 1500 LT Trail Boss
6 Great Deals out of 37 listings starting at $18,750
-
Chevrolet Silverado 1500 Custom
5 Great Deals out of 32 listings starting at $15,488
-
Chevrolet Silverado 1500 1LT
10 Great Deals out of 28 listings starting at $6,750
-
Chevrolet Silverado 1500 WT
8 Great Deals out of 27 listings starting at $10,988
- ${price_badge()}
- ${ami_badge()}
- ${battery_badge()}${ev_report_link()}
- ${hot_car_badge()}
- ${award_badge()}
- ${cpo_badge()}
${price_badge_description}
${ami_badge_description}
The EV Battery Rating is based on this vehicle's current expected range relative to the vehicles expected range when new. ${battery_badge_text}
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.
${award_blurb}
${award_two_blurb}