Used Jeep Cherokee for sale near Oconomowoc, WI under $20,000

Like the look and has plenty of power we have the v6 option The interior is very comfortable with all the bells and whistles you can appreciate. We traded in a Liberty and the ride is so much smoother.

I had an awesome experience at this dealership. Everyone I dealt with was very friendly and helpful. There was no need to haggle over pricing, they were upfront and fair in not only the cost of the vehicle I purchased but the trade in I had was priced more then fair. I live in Milwaukee and it was well worth the trip to Waukesha!!!

Overall, pretty decent car. As professional reviews will note, the transmission is a little finicky, but nothing over the top. Learn to work with it, it works with you. Bought this car used last year with 68k and I drive a lot, so I've already put 30k on it. Handling wise, this works great, even in the snow (FWD, not 4x4). Good cargo room, and room for the kiddo's carseat. Now, this is a Jeep, and hasn't been without issue. The front struts have been replaced, probably as part of my driving style and the rough roads in my area. Part of the bumper got pulled off a while back, not a big deal. Mechanically, decently sound, the car has thrown a few check engine lights but for non-issues. It had an issue a while back where it would turn off or restart on its own when stopping (not to be confused with the auto-stop, which is annoying but can be turned off, this car would just flat out turn off), but that fixed itself. Developed an engine tick that does appear in Jeeps, but that has also righted itself. As such, no major maintenance has needed to be done besides my struts. So all in all, it works. If you're in a situation like mine, yeah, buy the 2019.

3/3/2025 I bought a another car from Honda in waukesha David has helped me out again and disappoint me. David was so kind and understanding and didnt pressure me in to anything. If you want a car Wilde Honda of Waukesha is the place to go to. Ask for David trust me you will not be disappointed. Wilde Honda always goes above and beyond in helping there guests get the right car for the right fit. Thank you David again to all the staff great Place !!! :)

I drive a lot my car is a 2014 and it has currently 277,400 miles and still ticking. I’ve had very few maintenance issues overall the basic wear and tear as expected! I didn’t expect it would last as long as it has but I am being pleasantly surprised. It is great on gas compared to most SUVs and overall a comfortable car !

I live 1000 miles away, but their price is so competitive that I may make the trip there yet. I inquired at several local and regional dealers and without exception, Russ Darrow was the most responsive. Robert Garcia didn't try to avoid my very specific questions on cost and definitely made a great impression on me.

I have a 2018 Cherokee latitude plus. More than 140k miles. Very nice SUV. I think most of this bad reviews are not fair. I will buy a new one in the near future.

The Boucher team has always made us feel like family whenever we do business with them. Mike Hanson, Scott Foote, and Mike Garrett all went above and beyond to make sure we were taken care of. 5+ star service. We will be a life long customer for sure!

I like this car a lot. I gave up a lot of interior space when I traded in my Journey for the Cherokee and the ride is not quite as smooth along with less gas milage but every other way it is far superior. Love the 4x4 and how it handles in snow. The interior design is very nice as is the exterior design. More sleek. It is still a nice comfortable ride, especially on the highway. It is much more reliable than my last car. The seat and steering wheel warmers are an extremely nice touch. Yea, I like the Jeep Cherokee very much.

I travelled out of state for my purchase and Brad did a great job at answering my multitude of questions! They had a driver pick us up at the airport(1 hour away), washed and filled up the car. Brad sat down with us helped us find some local eats and got us convict way with ease. Paperwork was quick as well. I can't thank them enough for making this car buying experience very productive and hassle free! Thanks again Brad!

I have been looking at new Jeeps for awhile was needing a new vehicle was driving a 2005 dodge grand caravan sxt drove it everywhere kid's learned how to drive in it. But I'm a jeep guy have a 1979Jeepcj7 since brand new drive it daily. Seen the jeep cherokee trailhawk at my local dealership talked to them about it took it for a test drive and fell in love with it. Had to take it home. Very comfortable all the buttons are in the right places. Display screen is very simple to navigate easy-to-use app's phone linked right up no need to look at it. Mics are in right places above head everyone I call or calls me has no problem hearing me. Has alot of safety features to get use to but not hard. I have had other cherokee in the past but love this one. If you are interested in a Jeep check out the Cherokee line like I said I'am a Jeep guy test drive and you will see what I mean.

It was my first time buying a car and they made it as easy as possible. I was a bit nervous at first but they broke everything down and didn't leave a detail out. Customer service was awesome. Everyone was helpful and polite. And they filled up the gas tank before handing me the keys!!

I bought my 2019 Cherokee new in July 2019. I have had it for 4 and a half years now and I have had no problems at all. I have over 61k miles on it. I do worry about the warranty being up that something might happen but it has not given me any issues so I shouldn't really be letting it bother me. This is the longest I have had a vehicle. I usually keep a car and trade it in around 3 years but I have loved driving this car so much that I have no desire in letting it go. I hate that Jeep is no longer producing more of these.

i did my homework prior to our recent purchase of a low mileage used Mercedes. One of my primary information sources was Cars.Com. and the other was Car Max. We visited the Kenosha Car Max and found everyone we had contact with to be professional and informative. We ultimately bought a car from a Mercedes dealer but did sell our trade to Car Max Waukesha. The experience was handled quickly and pleasantly. I would definitely recommend Car Max and their staff.

Would recommend this vehicle. Overall very good value and has proven very reliable. Sorry to hear it is being discontinued Jeep had a winner and what I thought was a great tweeter between the Compass and Grand Cherokee.

I was so happy dealing with my salesman Bill Johns Jr. in Mukwonago. He was super helpful and very knowledgeable. He went out of his way to make it a pleasant experience. He got back to me right away with answers to my questions and I will definitely come back if buying another car. Thanks Bill

We purchased the same night a wrangler sport JLU 3.6 manual trans and this Cherokee Limited with the same engine and the 9-speed automatic. And oh boy, these cars were completely different despite having the same 3.6 Pentastar engine. Launching the Wrangler was never an issue. Launching the Cherokee and even more reaccelerating was truly painful and required a lot of preparation. Sometimes, the transmission would take few seconds before downshifting making the throttle response slow at best. Other than that, the car proved to be reliable and was extremely silent and very well equipped. I would recommend that car as a commuter for someone who is not seeking any driving fun. For families who enjoy long trips, there are better and more responsive options out there.

Spike was very helpful and understood my needs Got me setup with the perfect vehicle for my situation. Would highly recommend him and the dealership

The Lot was clean and presentable, there was plenty of info displayed on each vehicle. We weren’t pressured to buy anything, Gary was very helpful and gave us the space to make my own decision. Once I decided, they made sure the total price was in my price range, and made the final paperwork a breeze to get through. Even though it was a As Is sale, they made sure I had options for after if I had any concerns. Thank you Gary for making it an easy decision and a quick process.

I have a red 2017 Jeep Cherokee that I bought used, and I love it. I live in the blue ridge mountains of Virginia and this car has been able to deal with everything i've thrown at it. Deep snow, muddy trails, icy roads... You name it. I have the V6 and I can hook up a heavy uHaul trailer and go up and down all the mountains with it. My wife even hit a deer in this car... It obviously had to go to the repair shop, but my wife was safe. The only thing that bothers me a little is that you can't slam on the brakes and throw it in reverse... You need to stop completely, take two seconds and then put it in reverse.

Friendly and accommodating. Our salesman was Jeff Schultz and he was helpful and answered our questions. The car had been cleaned up great and what needed fixing was done. Our first purchase of a used car and it was 5 star!!

Great SUV...BOUGHT in 2017...good on gas penalty of zip with V6 engine. The start stop stop working last year and found out why.I needed a new battery as went dead this year...now start stop feature works 100 percent. Have low milage 30000 miles or 50000 kms here in Canada. .

Great knowledge of the car and very helpful getting it financed Very caring people to work with

I have just bought this used Cherokee. 70,000 miles I Like it a lot so far. Except I am having a little trouble with my blind spots. Not used to being so low compared to my Ranger Truck. I have a good upgrade. Pretty good milage. Everybody says I got a good deal and so far so good. Drives very nice.

We bought a Toyota Sequoia and noticed a couple of things that were a little off like the mirror the motor was out. They also did an inspection and found the back window did not go down so they ordered all the parts right away. Customer service is excellent! We worked with Jairo and is always willing to answer our questions at anytime taking our worries away. I work in sales and can see the Hussle they put in.

Purchased new in 2015. Have only done 1 repair in 129k, which was fixing oil leak at oil filter housing. Solid car, great in rain and snow. Thoroughly enjoy this car

Walked on lot, not even knowing I was buying a car. All my relatives are now customers of Diamond Jim's. Sales staff are courteous, knowledgeable and great to work with! I purchased a 2014 Audi and couldn't be happier!

A few years ago I bought a 2014 Jeep Cherokee Latitude, at the time it had 24,000 miles. Today it has 68,000, at the time it was a really good upgrade from my last vehicle, a 2005 Dodge Grand Caravan. I loved the comfortable cloth seats, the V6 engine had tons of power for commuting and good gas mileage (I've gotten over 30 on the highway). After 5 years of owning my Cherokee it has never let me down, it has only gone into the shop for a CV Axle, which Chrylser had paid for most of, and tires. Now that my Jeep is going on 7 years old, I'm in the market for another car, I've not even considered anything other than a 2021 Jeep Cherokee, especially because I am considering leasing and lease deals are awesome with Jeep / Chysler.

Nice and clean vehicles and it was quick and easy and the workers were very friendly

Overall very capable vehicle. 3.2L with 4wd/factory trailer tow. Silly things show up like the service 4wd light that comes/goes and radio/controller that resets after replacement. Solid car with a good pedigree.

Great place to make a great deal on a new Kia Seltos EX. All of the people working there were fabulous. They took that nasty, anxious edge of buying a car and tossed it right in the garbage 🗑️ Anna was a special lady and very informative and gracious to us. She answered all questions and helped iron out various small things along our journey at Russ Darrow in Waukesha. Best Deal Ben came alongside Anna and really helped to seal this deal for us. No problem or pressure for us at all. Anna listened to our story and empathized with us. She really helped us out. Shannon in finance was terrific and she went above and beyond to assist us, explaining different items and financing options for us. GREAT experience, please give Anna the Best salesperson award for at least the month of April 2024. Thanks again for the nice experience of buying from your dealership.

I love my Cherokee overall. This is my 3rd one. Sadly I've noticed the quality slipping. Jeep no longer provides a spare tire - WHAT? The floor mats are now of lesser quality and no longer have the Jeep emblem embroidered on them. The transmission is still a little iffy but not as bad as my '15. The tail lights fill with condensation but the dealership tells me it is normal to do so - WHAT? Additionally you're never gonna be able to find a V6 anymore. I had to go down a year to a '22 in order to get one. They are pushing EVs and Hybrids. All this being said I'm still Jeep girl and still love my Cherokee.

Love the interior and exterior , has all the features I need and will use ! Very sexy car :) I love the fact I can take my fur babies to beach now . They love to ride.

the car is largest enough to haul baseball equipment around, yet easy parking and handling. i like the interior and the room. the seats are very comfortable