Used Chevrolet Silverado 1500 Custom Trail Boss for sale near Winnetka, IL

I purchased a great vehicle yesterday. The staff were all polite & friendly. Jorge was great.👏🏾He made sure I got what I was looking. I would definitely recommend him & Webb Chevy to anyone looking to purchase a vehicle.

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.

I called in the morning with an alert about the oil level And without an appointment, I was told I could just come in anytime I was able. The service department was efficient and competent at addressing the issue. Thank you!

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.

Awesome service department. Service like that remind me of why I keep coming back to this dealership for service. Shout out to Mike, John and their techs!

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.

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 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.

Purchase service was fairly quick. Car is beautiful, everyone loves it! the entire staff was very friendly and welcoming during our visit. We would recommend this dealership.

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.

Favian Valdivia is a very kind and friendly person He takes the time to explain what is happening and what needs to be done ?

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.

The Team that my husband and I worked with Dillon, Tim & Dan, were all very helpful and courteous. We had a certain price point and they managed to get us very close to where we needed to be AND we got the car we really wanted. Buying process was seamless, communication was great, and customer service was wonderful. This was our second purchase with Haggerty and we highly recommend!! Thank you

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.

Jezabel and Daniel were extremely helpful in our search for a new vehicle. They were knowledgeable about both of the vehicles we tested and made the purchasing process very easy and quick.

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

Trent greeted me as soon as I stepped out of my car. He told me that I was going to receive VIP treatment and he did not disappoint me. He did a presentation of both MDX that I wanted to see by having all doors open and a brief walk through and overview of the features before the test drive. He was knowledgeable, courteous, respectful and absolutely the best car sales experience I’ve ever had in my entire life.

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.

I had a great experience working with Toni the salesman, he answered all of my questions. i bought a BMW x5 the other day, for a great price. there was a small ding that i notices afterwords (a very minor ding). He gave me bindis number (the service advisor) and they took care of it. Awesome dealership and I will be recommending to friends and family.

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?

Excellent experience from the purchasing process with Robert to the wonderful folks in the service area. Excellent all around.

When I first drove this truck I fell in love with it. I am recommending this truck to everyone I know. It’s got great power and it is comfortable. It rides surprisingly smooth.

Krystal helped us in finding a new tahoe. She had great knowledge and made the process quick and smooth.

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.

My husband and I went in late and met Ismael Ramirez and his manager Edgar which were very professional and very easy to work with. We’ll definitely come back for another vehicle.

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.

I made an appointment for an oil change & my car was making a sound when braking. Carlos went above and beyond to have my car inspected & find out exactly what the problem was. I have never been disappointed. I know I?m in good hands with Carlos!

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.

I initially bought my car in July 2022. Our old family car broke down and needed a car. I had been window shopping for cars and looked but I didn?t see a car that stuck out to me until I saw the Buick Envision and fell in love with it and the color. The staff was super helpful throughout the buying process and I?m super happy with my purchase, I haven?t had my first oil change yet but I will def get that done soon at my dealer.

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.

I only visit this dealership because Carlos is working in the service center. He is always great. He takes care of my vehicle quickly and I can always trust that my vehicle is fixed right.

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.

Thank you for getting my cehicle repairs done and workinf so hard to het me out of there to get to where I needed to go.

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.

Somehow the rear window wiper blade cover on my 2019 Buick Encore went missing.... Being a long-time friend and customer of Mike's, I went to his GMC service center for replacement, and was grateful that Bill Haggerty replaced the missing cover without charge! As always been my experience, GREAT service and GREAT dealership! ...Tom Noble

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.

Great place to buy a vehicle. The staff is very friendly and the process was very easy

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

Kris Kevorkian was such a great sales and got us a great deal on a new car.

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