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 LT 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 LT 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.
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.






Certified
2019 Chevrolet Silverado 1500 LT Trail Boss
Vehicle information
Features
Reviews
It is good to have good people work for you.
I had a positive experience with Al Piemonte Ford in Melrose Park. I just lost my father. My dad did business with them when he was alive, and recommended them. Eddie Rodriguez was the sales agent that took care of him. He remembered me, was compassionate, knowledgeable, helpful and expedited the transaction in a fair manner. Thank you.
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.






Chevrolet Certified
2023 Chevrolet Silverado 1500 LT Trail Boss
Vehicle information
Features
Reviews
WE’RE WALKING OUT WITH A TRUCK!
WE’RE WALKING OUT WITH A TRUCK!!!! We are so happy and satisfied with our purchase today with Rheya! She was so much fun to shop with and very knowledgeable and able to answer all our questions and concerns. Manager was also very helpful and delighted to help up walk out with the price we were looking for !!! Come get your Chevy here!!! You won’t regret it!!! ❤️❤️❤️
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 LT Trail Boss
Vehicle information
Features
Reviews
Michael Raczkowski was an accommodating, patient and very
Michael Raczkowski was an accommodating, patient and very friendly gent. It was an a good experience dealing with him. Also. Manager Bob Wolf was awesome as well.
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
2021 Chevrolet Silverado 1500 LT Trail Boss
Vehicle information
Features
Reviews
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.






Chevrolet Certified
2025 Chevrolet Silverado 1500 LT Trail Boss
Vehicle information
Features
Reviews
The Advisor Tony and mechanic Technician Klaus are the
The Advisor Tony and mechanic Technician Klaus are the best. I give both of them 10 Stars for such great service. These two both strive to achieve the performance level of Excellence in their jobs everyday. Thank you for such great work
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
2022 Chevrolet Silverado 1500 LT Trail Boss
Vehicle information
Features
Reviews
Chris and Matt are all world!
Chris and Matt are all world! Love my car and our entire experience buying from them. Very responsive and dependable. Knowledgeable as well. Joey
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 LT Trail Boss
Vehicle information
Features
Reviews
Five-Star Experience at Castle Chevy Our experience at
Five-Star Experience at Castle Chevy Our experience at Castle Chevy was truly outstanding from start to finish. After receiving an invitation in the mail, we were contacted by Linda, who was not only friendly but also incredibly helpful. She took the time to understand our situation and helped us consider whether buying a car after bankruptcy was the right step. Her guidance was thoughtful and never pushy. When we visited the dealership, Kevin took over and exceeded our expectations. I had some hesitation due to our financial past, but Kevin was patient, professional, and informative. He clearly explained how purchasing a vehicle could help us begin rebuilding our credit and finally get out of a costly car rental situation. What impressed us most was Kevin?s genuine commitment to our needs. He didn?t try to steer us toward just any vehicle?he helped us find the right one for us. He also worked hard to secure the best possible financing available. The entire process, including the paperwork, was smooth and stress-free thanks to his outstanding support team. Although I don?t remember every staff member?s name, I won?t forget how respectfully and kindly we were treated throughout. At Castle Chevy, we never felt like just another number. The team made us feel valued and respected. That?s why I?m giving them a well-deserved 5-star rating.
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.






Certified
2019 Chevrolet Silverado 1500 LT Trail Boss
Vehicle information
Features
Reviews
Excellent experience with the dealership and the staff I?
Excellent experience with the dealership and the staff I?m a repeat customer for life and I definitely will refer friends and family to this dealership in all my years of buying cars. This has been the best experience I have ever had so I?m customer completely
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
2024 Chevrolet Silverado 1500 LT Trail Boss
Vehicle information
Features
Reviews
Bill Wilson, he was a pleasure to work with
Bill was outstanding. Never felt pressured and was very patient. Would highly recommend him for your auto buying needs. Bill takes away all the negative things associated with the car buying process.
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
2020 Chevrolet Silverado 1500 LT Trail Boss
Vehicle information
Features
Reviews
i was in and out.
i was in and out.. very good experience and i will give my salesman marco torres as much business as i can.. thanks conway imports!
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.






Chevrolet Certified
2023 Chevrolet Silverado 1500 LT Trail Boss
Vehicle information
Features
Reviews
Tahoe purchase
We bought a '23 Tahoe Z71 and the sales process couldn't have been more seamless. Our salesman, Paul Degrazia, was terrific and made the purchase an enjoyable process, which is pretty rare. We came to terms quickly and we were finished within a couple hours. We love the vehicle and definitely recommend Bill Kay and Paul.
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 LT Trail Boss
Vehicle information
Features
Reviews
Got more than I had asked for
I thought Josh was wonderful. Not only did he take care of the items I had asked him to, but he also reattached a piece of trim that was loose. I was very pleased!
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
2024 Chevrolet Silverado 1500 LT Trail Boss
Vehicle information
Features
Reviews
I had the pleasure of working with Jeffrey Serwas at
I had the pleasure of working with Jeffrey Serwas at Advantage Chevrolet of Hodgkins & Countryside, and I was genuinely impressed. He was professional, personable, and made me feel welcomed—like I was a regular, part of the family. He took my concerns seriously and made sure I felt heard and valued. I don’t usually like name-dropping dealerships, but I have to be honest. I purchased two fully loaded Suburbans from Castle Chevy North, and yet, I still don’t feel welcomed or appreciated there. I barely get a proper greeting and often feel like a bother rather than a valued customer. The level of service and hospitality at Advantage is truly above reproach. Even though it’s a further drive for me, I will gladly make the trip just to work with Jeffrey moving forward. Thank you for such a refreshing and professional experience.
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
2023 Chevrolet Silverado 1500 LT 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
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
2020 Chevrolet Silverado 1500 LT 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.
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
2021 Chevrolet Silverado 1500 LT Trail Boss
Vehicle information
Features
Reviews
“Excellent Communication
My first experience at this dealership will definitely bring me back. We are so happy with our purchased! We had Alex Alverio from Sales, he was very professional & helpful, has awesome customer service & we highly recommend Alex. Thank you so much and keep it up!
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
2023 Chevrolet Silverado 1500 LT Trail Boss
Vehicle information
Features
Reviews
Jerry McDuffie has always been a pleasure to work with.
Jerry McDuffie has always been a pleasure to work with. Our family and friends have purchased several cars from him over the last 20 years. He always gives you a fair deal and takes the time to make sure you get the car that is right for you. He is very patient in dealing with us seniors who can be technically challenged about some of the new car features on today's modern cars. I highly recommend Jerry for anyone looking to buy a new or used 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.






Used
2023 Chevrolet Silverado 1500 LT Trail Boss
Vehicle information
Features
Reviews
Nora was great!
Nora was great! Took the time to help find the right vehicle. She was patient and was great to work with! Mary G.






Used
2019 Chevrolet Silverado 1500 LT Trail Boss
Vehicle information
Features
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!
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.
-
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 LT Trail Boss by city
-
Chevrolet Silverado 1500 LT Trail Boss in Lincolnwood, IL
4 Great Deals out of 29 listings starting at $26,880
-
Chevrolet Silverado 1500 LT Trail Boss in Evanston, IL
3 Great Deals out of 22 listings starting at $28,839
-
Chevrolet Silverado 1500 LT Trail Boss in Morton Grove, IL
4 Great Deals out of 29 listings starting at $26,880
-
Chevrolet Silverado 1500 LT Trail Boss in Wilmette, IL
3 Great Deals out of 22 listings starting at $28,839
-
Chevrolet Silverado 1500 LT Trail Boss in Niles, IL
4 Great Deals out of 30 listings starting at $26,880
-
Chevrolet Silverado 1500 LT Trail Boss in Kenilworth, IL
3 Great Deals out of 22 listings starting at $28,839
-
Chevrolet Silverado 1500 LT Trail Boss in Winnetka, IL
3 Great Deals out of 22 listings starting at $28,839
-
Chevrolet Silverado 1500 LT Trail Boss in Northfield, IL
3 Great Deals out of 27 listings starting at $26,880
-
Chevrolet Silverado 1500 LT Trail Boss in Glenview, IL
4 Great Deals out of 30 listings starting at $26,880
-
Chevrolet Silverado 1500 LT Trail Boss in Park Ridge, IL
4 Great Deals out of 30 listings starting at $26,880
-
Chevrolet Silverado 1500 LT Trail Boss in Harwood Heights, IL
5 Great Deals out of 30 listings starting at $26,880
-
Chevrolet Silverado 1500 LT Trail Boss in Norridge, IL
5 Great Deals out of 31 listings starting at $26,880
Chevrolet Silverado 1500 LT Trail Boss by year
-
2026 Chevrolet Silverado 1500 LT Trail Boss
20 listings starting at $58,149
Chevrolet Silverado 1500 by trim
-
Chevrolet Silverado 1500 LT
13 Great Deals out of 82 listings starting at $2,500
-
Chevrolet Silverado 1500 RST
6 Great Deals out of 46 listings starting at $29,800
-
Chevrolet Silverado 1500 LTZ
8 Great Deals out of 37 listings starting at $4,995
-
Chevrolet Silverado 1500 WT
4 Great Deals out of 32 listings starting at $10,988
-
Chevrolet Silverado 1500 Custom
3 Great Deals out of 28 listings starting at $20,695
-
Chevrolet Silverado 1500 1LT
7 Great Deals out of 25 listings starting at $12,995
-
Chevrolet Silverado 1500 Custom Trail Boss
2 Great Deals out of 21 listings starting at $19,945
- ${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.