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
Skokie, 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
2021 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features
Reviews
Battery
Todd was very helpful and made sure my car was pulled inside when leaving as it was very slippery outside
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
2019 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features
Reviews
I had such a great experience at Elite Motors.
I had such a great experience at Elite Motors. Carl and Michelle were very helpful and the entire team was excellent as well. Highly recommended to everyone.
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
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!
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
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
2022 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features
Reviews
Good experience fast service
I had a good experience with Chris Price awesome sales man.. no pushy sales tactics.. he was honest and straight to the point.. I have bad credit.. and was turned down from alot of different dealers Marino, Hawk,Naperville and Shermans.. all said No.. but Carmax have me thre car I wanted wth super low miles.. Thanx Chris you a good guy 🤗
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
2022 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features
Reviews
Erick was amazing to work with—patient, friendly, and
Erick was amazing to work with—patient, friendly, and just a really good guy. You can tell he cares about people, not just the job.
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
2020 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.
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
2024 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features
Reviews
Everyone in the dealership was nice and helpful.
Everyone in the dealership was nice and helpful. Big shout out to David and Johnny for having delivering great customer experience and drive out their lot happy
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
2021 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features
Reviews
Great experience.
Great experience. Alex was a charm to work with for the truck I been wanting.
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






Chevrolet Certified
2021 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features
Reviews
Michael Rancharan at Woody Buick GMC was a pleasure to
Michael Rancharan at Woody Buick GMC was a pleasure to work with. The whole buying experience was smooth, transparent, and positive.
2021 TB LT 5.3L L84
5.3L, 18,000 miles, 2021 TB LT and have had no real issues. Ebrake triggered a warning message which was reset 1,000 miles ago no warning light since. MPG is decent but if you like to drive a vehicle it will be 13-14mpg. Wish the exhaust made real noise and GM loves thier 33's, come on 35s look fantastic. I had a 2017 LT Z71 5.3L L82 and had no issues at 65,000 miles when I traded her in.






Used
2024 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features
Reviews
Steve was very up front from the very beginning.
Steve was very up front from the very beginning. Thank u for ur help Steve
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.






Chevrolet Certified
2023 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features
Reviews
Emily Salcido, our Service Consultant was excellent.
Emily Salcido, our Service Consultant was excellent. She listened to our concerns and made sure she understood everything was correct for the mechanics, made sure we were happy with our experience and just took great care in our experience. Highly recommend this dealership and Emily!
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
2022 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features
Reviews
Quick and painless purchase with financing.
Quick and painless purchase with financing. Did most of it via text and phone call and agreed to a price and showed up the next evening to pick up the car. Could not have been simpler! Ruben the sales rep was great!
My 2022 Silverado has not on the road long enough.
Driving not as good as my 2011 Silverado 6.2 what great truck for power and performance during long trips from Baltimore to Atlanta. Other than rear brakes problems there are no major issues






Used
2023 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
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
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.
DEF found in diesel fuel tank in my new truck
I love my new 2021 Chevrolet high country truck except for the location of Def and Diesel that they are located in the same compartment without any lids to identify the 2, for some strange reason l got Def in my diesel, the insurance company will not pay for this so it’s costing me over $13,0000 out of my own pocket to get fixed and keep the warranty good still. Chevrolet needs to be responsible for this. If this is such a problem that can happen to anyone at anytime. They need to separate the def and the diesel from the same location so that it can not accidentally put DEF into the diesel spout or if someone comes along and puts DEF into your diesel and your insurance will not cover the repairs as they blame you. To fix this huge mistake, Chevrolet will have to correct this by installing locking cover over the spout like most vehicles have and put a fuel cap back on, move the DEF back under the hood in a accessible area. I am saddened by all of this and the cast of all this has set me back as l am only surviving day by day due to all the rising costs today. Hope Chevrolet reads this and others that could potential have this happen to them. My new truck will never be the same again. One more thing to add, the mechanic mentioned that this was the 7 th Chevrolet truck that this happened to this year alone.






Chevrolet Certified
2022 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features
Reviews
Excellent help with trading in my used 2016 Chevy
Excellent help with trading in my used 2016 Chevy Silverado. It had some right side damage, but Victor and the sales staff helped me out with a trade in.
2022 Chevrolet Silverado High Country 6.2 V8
My 2022 Silverado High Country was involved in a car accident caused by a teen, and the truck saved my life, the emergency collision system reacted right away, prevented an even worse outcome. I can't wait to fix my truck. It's amazing in every way, its quite a looker too. I had just done a 4" Lift Kit and was about to throw on some 35s, can't wait to do that, here soon. I would recommend this truck to everyone. Chevy really did am amazing job, with inside and outside, just an amazing truck overall.






Used
2022 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features
Reviews
Excellent.
Excellent. Upfront, thorough, and personable. Have checked in after our purchase to ensure satisfaction and answer any questions. Much appreciated!






Used
2020 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features
Reviews
AMAZING PLACE!
AMAZING PLACE!!! I bought a 2021 Kia and I had it shipped to my house in Texas, extremely smooth process and it was a lot better than I expected it. Thank you Midway !! I will be back in the future!!!
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?






Chevrolet Certified
2024 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features
Reviews
there are always there for customer satisfaction, and
there are always there for customer satisfaction, and fast service. They always stay on too of repairs 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
-
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 Lincolnwood, IL
1 Great Deal out of 25 listings starting at $28,000
-
Chevrolet Silverado 1500 Custom Trail Boss in Evanston, IL
1 Great Deal out of 21 listings starting at $28,000
-
Chevrolet Silverado 1500 Custom Trail Boss in Morton Grove, IL
1 Great Deal out of 26 listings starting at $28,000
-
Chevrolet Silverado 1500 Custom Trail Boss in Wilmette, IL
1 Great Deal out of 21 listings starting at $28,000
-
Chevrolet Silverado 1500 Custom Trail Boss in Niles, IL
1 Great Deal out of 26 listings starting at $28,000
-
Chevrolet Silverado 1500 Custom Trail Boss in Kenilworth, IL
1 Great Deal out of 21 listings starting at $28,000
-
Chevrolet Silverado 1500 Custom Trail Boss in Winnetka, IL
1 Great Deal out of 22 listings starting at $28,000
-
Chevrolet Silverado 1500 Custom Trail Boss in Northfield, IL
1 Great Deal out of 30 listings starting at $25,877
-
Chevrolet Silverado 1500 Custom Trail Boss in Glenview, IL
1 Great Deal out of 30 listings starting at $25,877
-
Chevrolet Silverado 1500 Custom Trail Boss in Park Ridge, IL
1 Great Deal out of 26 listings starting at $28,000
-
Chevrolet Silverado 1500 Custom Trail Boss in Harwood Heights, IL
1 Great Deal out of 23 listings starting at $29,998
-
Chevrolet Silverado 1500 Custom Trail Boss in Norridge, IL
1 Great Deal out of 23 listings starting at $29,998
Chevrolet Silverado 1500 Custom Trail Boss by year
-
2025 Chevrolet Silverado 1500 Custom Trail Boss
22 listings starting at $44,975
Chevrolet Silverado 1500 by trim
-
Chevrolet Silverado 1500 LT
12 Great Deals out of 57 listings starting at $5,997
-
Chevrolet Silverado 1500 RST
6 Great Deals out of 49 listings starting at $28,595
-
Chevrolet Silverado 1500 LT Trail Boss
3 Great Deals out of 39 listings starting at $24,950
-
Chevrolet Silverado 1500 LTZ
9 Great Deals out of 35 listings starting at $18,995
-
Chevrolet Silverado 1500 1LT
9 Great Deals out of 28 listings starting at $9,999
-
Chevrolet Silverado 1500 2LT
9 Great Deals out of 26 listings starting at $15,995
-
Chevrolet Silverado 1500 Custom
4 Great Deals out of 26 listings starting at $19,595
- ${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}
Certified cars are manufacturer warrantied and typically go through a rigorous multi-point inspection.
This car is likely to sell soon based on the price, features, and condition.
${award_blurb}
${award_two_blurb}