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
Glenview, 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
Great place to buy a vehicle.
Great place to buy a vehicle. The staff is very friendly and the process was very easy
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
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.
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
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.
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
We just had a very positive and smooth interaction and
We just had a very positive and smooth interaction and used car purchase with Castle Chevrolet. We were shopping for a replacement Chevy Trax for my 86 year old mother in law and I found one on Castle's web site that was a perfect fit for her. I phoned the dealer to let them know we would be coming in. We were met by Jeff Vicari who handles our entire transaction and sale in a professional, courteous and respectful manner. My typical opinion of dealing with buying a car normally isn't very favorable but this experience was awesome. We did have a minor issue with the loan paperwork but it was our fault, I contacted Jerome Witt ( Sales Manager) who said he would fix the problem - low and behold, it was fixed within the hour. My thanks to both of these guys for making the transaction positive!
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
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
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
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.
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.






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
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
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!!!
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
2021 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features
Reviews
Enjoy the team at Ray.
Enjoy the team at Ray. Hugo is a great sales associate and the service team I fully trust with all my needs. Luis has been great and goes out of his way to make sure my vehicle is in top condition.
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.
There are additional matching cars outside your search area.
Partial matches are generated by applying your search criteria to a larger search area. Our goal is to help you discover additional cars that match your search preferences.
As a benefit to some of our dealer customers, we display their listings first.






Chevrolet Certified
2024 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features






Used
2022 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features






Used
2019 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features






Used
2022 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features






Used
2024 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features






Used
2020 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features






Used
2024 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features






Used
2024 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features






Used
2019 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features






Used
2023 Chevrolet Silverado 1500 Custom Trail Boss
Vehicle information
Features
-
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 Glenview, IL
2 Great Deals out of 29 listings starting at $25,877
-
Chevrolet Silverado 1500 Custom Trail Boss in Northfield, IL
2 Great Deals out of 29 listings starting at $25,877
-
Chevrolet Silverado 1500 Custom Trail Boss in Morton Grove, IL
2 Great Deals out of 24 listings starting at $28,000
-
Chevrolet Silverado 1500 Custom Trail Boss in Northbrook, IL
2 Great Deals out of 30 listings starting at $25,877
-
Chevrolet Silverado 1500 Custom Trail Boss in Niles, IL
2 Great Deals out of 24 listings starting at $28,000
-
Chevrolet Silverado 1500 Custom Trail Boss in Winnetka, IL
2 Great Deals out of 20 listings starting at $28,000
-
Chevrolet Silverado 1500 Custom Trail Boss in Glencoe, IL
2 Great Deals out of 26 listings starting at $25,877
-
Chevrolet Silverado 1500 Custom Trail Boss in Park Ridge, IL
2 Great Deals out of 24 listings starting at $28,000
-
Chevrolet Silverado 1500 Custom Trail Boss in Des Plaines, IL
2 Great Deals out of 29 listings starting at $25,877
-
Chevrolet Silverado 1500 Custom Trail Boss in Skokie, IL
2 Great Deals out of 23 listings starting at $28,000
-
Chevrolet Silverado 1500 Custom Trail Boss in Prospect Heights, IL
2 Great Deals out of 31 listings starting at $25,877
-
Chevrolet Silverado 1500 Custom Trail Boss in Deerfield, IL
2 Great Deals out of 32 listings starting at $25,877
Chevrolet Silverado 1500 Custom Trail Boss by year
-
2025 Chevrolet Silverado 1500 Custom Trail Boss
25 listings starting at $44,975
Chevrolet Silverado 1500 by trim
-
Chevrolet Silverado 1500 LT
18 Great Deals out of 78 listings starting at $5,997
-
Chevrolet Silverado 1500 RST
9 Great Deals out of 59 listings starting at $28,595
-
Chevrolet Silverado 1500 LT Trail Boss
4 Great Deals out of 43 listings starting at $24,950
-
Chevrolet Silverado 1500 LTZ
10 Great Deals out of 36 listings starting at $18,995
-
Chevrolet Silverado 1500 Custom
6 Great Deals out of 32 listings starting at $19,595
-
Chevrolet Silverado 1500 1LT
9 Great Deals out of 29 listings starting at $9,999
-
Chevrolet Silverado 1500 Custom Trail Boss
2 Great Deals out of 29 listings starting at $25,877
-
Chevrolet Silverado 1500 2LT
11 Great Deals out of 26 listings starting at $16,995
-
Chevrolet Silverado 1500 High Country
22 listings starting at $22,990
- ${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}