Used Jeep cars for sale near Winnetka, IL under $899,990

We were looking for a moderately priced Jeep Wrangler Unlimited for a teenage son and this one fit the bill. For a roughly 8 year old vehicle it was well taken care of by previous owners. Although the Jeep Wrangler Unlimited won’t be confused with a luxury car for its ride and comfort, they are adequately appointed and fun to drive. That’s where the saying, “it’s a Jeep thing “ comes from. All I know is that in our area they are very popular and our teenage son will thoroughly enjoy it if he can ever get it away from his Mom.

I purchased it used in 2022, it had 76k and now has 96 in 2025. It's 4wd with the 5.7 Hemi in the Overland trim. It hasn't given me any trouble.

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.

Healthy clean environment, that did not push me to try and purchase a car. They took there time in making sure all my needs are met and made sure all my questions were answered would certainly recommend this place to friends and family

One of the best vehicles I have ever owned! Dependable, lots of features, stylish, fun to drive on and off road. A vehicle you can enjoy and be proud of!

Made a online appointment came in and they did a oil change and tire rotation. Happy with the service.

I have never owned a Jeep before and barely even considered an SUV. I've always been a luxury sedan guy, but this Jeep Grand Cherokee L Overland 4x4 has completely changed my mind. The exterior and interior designs are on par with most SUVs and remind me of the luxury sedans I have previously driven. Tech options are better than I've ever had in any other car. The ride and comfort are better than anything I've ever experienced before. Very dependable so far but I'm still under 1000 miles. I'm very pleased with my purchase decision.

From originally purchasing my car at Haggerty to having my car serviced at Haggerty, my experiences have all been positive. Everyone is friendly and answers all of my questions. Work is done well and on time.

I already owned this vehicle when I took it in for service. But. I love the vehicle. I haven't had any major problems with my Jeep Summit

I had another great experience over at Wickstrom! This is the second F-150 I've gotten from Michael Kajdanowski and both times have been quick and easy! If you're looking for a new vehicle, I highly recommend you reach out to him!

The dealer and sales people everyone was amazing. G was awesome! He stayed late and worked with me through everything! I could not have asked for a better experience with everything that happened this day.

We had an outstanding experience with Alex Lopez while choosing our new Lincoln Nautilus. From the very beginning, he was professional, friendly, and incredibly patient. He took the time to explain every detail, answer all our questions, and guide us step-by-step until we found the perfect vehicle. Alex made the entire process easy, transparent, and pressure-free, which we truly appreciated. His knowledge of the vehicles and his genuine interest in his customers really stand out. We are extremely happy with our new purchase and highly recommend Alex to anyone looking for top-quality service. Thank you for everything, Alex! 🙌🚗✨

I've been driving for 43 years now and have owned an array of different vehicles, however I've never been financially fortunate to purchase a luxury model - until now! I was looking for a mid size vehicle that would check many boxes for my snowy Michigan commutes, along with distant travel comfort to and from my cabin and some towing capacity. I have only had this for roughly 1500 miles and wow.. My first impression was luxury. So many base options included in a mid sized and mid priced SUV that pleasantly surprised me. Secondly was the ride quality. Both smooth and quiet and handling. I've read other reviews discussing power inadequacy, but not at all. Plenty of passing and get tup to speed power. Next was the snow. I have Michelin defender tires and wow - what have I been missing? The snow 4x4 duaratac features combined with these tires make this a beast in the snow, slush and rain. It definitely gives me a much more safety reassurance while driving in these conditions. I have not tried the towing yet and have not had any "reliable" issues to report, but we are very fortunate with our pick and one very capable snow commuter.

I was referred to Midway Dodge by my brother. He has purchased about 3 cars from here and never had an issue with any of them. I was skeptical but he insisted it was a hassle free place to shop and everyone treats him like family here. He was right! I spoke with Teresa who was great and made me feel comfortable about coming in and then I worked with Edgar Garcia. He was very straight forward and I appreciated his honesty. I recommend this dealership for buyers with less than perfect credit as well as excellent credit. Thank you guys!

This has been an amazing vehicle! Super comfortable and will buy again. Loved all of the tech and comfort features to make each trip the best. I have owned a lot of cars and this one has the most intuitive features by far.

We have received very good service with Theresa and Dj. I love my Jetta and they were so nice and gave us a free gift too

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.

This is my second truck from Woodys. One from Naperville one from Gurnee. And I was pleased every time. I was so pleased the first time I came back to look with them this time. Jamie was great! Friendly.. made sure he answered every question or concern.. safe to say my next trick will come from woodys as well! Team Woodys !!!

This vehicle met all of my needs. Excellent handling in the snow with the Snow setting. It’s a great car to drive in the summer as well. Dual sunroof and cooled seats.

Wonderful experience! Brian worked with us to find a car for me within my limited budget. We went through several test drives before we found the perfect fit. Brian was great-straightforward, patient, and pleasant throughout. The financing process was quick and enjoyable. The entire staff was accommodating, friendly, and fun even though the process kept everyone past closing. It's rare to be able to say you had a good time buying a car, but I can honestly say I did. I look forward to working with them again in the future and I highly recommend checking them out for your next car purchase.

I HATE is the warning 'Place Two Hands On Wheel' as it goes off even when I have both hands on the wheel - No matter where I place my hands on the wheel it goes off. Since it is connected to the Lane Departure feature in order to not have to hear a constant warning alarm for Two Hands on Wheel I have to turn off the Lane Departure feature (which I love).

Larry was Great! Awesome experience. In and out timingPlease buy your car from here. Couldn’t hvae asked for a better salesman to deal with amazing

My wife and I bought a 23' Jeep Compass Limited with 15K miles. We were looking for something small but also a vehicle that could offer 4x4. My initial impression of it at the dealership was that it has an awesome exterior paint color (granite crystal) and black wheels to compliment it. The car drives great on the highway and city. It's a very comfortable ride and the car can turn on a dime! I am currently averaging 30 mpg while commuting to work each day. I have noticed the car will sometimes have difficulty up shifting. As long as I apply more gas it eventually gets over it. Not a big deal for me as my last vehicle would do the same thing. The rear view camera is nice on the Compass, however it is completely useless at night. Overall we are very happy with our purchase.

Excellent experience with Doug and the whole team here! I knew what I wanted when I came in and they helped me find the right car at the right price! I would recommend them to anyone!

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 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.

Was at dealership shopping and this new Jeep Cherokee Lattitude came in on transport. Wanted it the minute I saw it. Jeep dealership had ordered it custom with every option I wanted. Blackout package, V6 a true dual exhaust, sport, power everthing, 4x4 etc. The 4x4 is excellent and never failed me! Its been flawless, aftermarket tuning has turned it into a screaming black speed machine. 112,000 miles so far. No issues with anything! Would buy another if they still made this Cherokee Latitude Special! One very satisfied customer!!!

Great experience. Alex was a charm to work with for the truck I been wanting.

I love my little JEEP compass! It’s runs well and is perfect for me and my needs! Holds all the baseball gear and more in the trunk!

Best dealer ever. Tatiana did a great job..She is very smart respectful and she has a lot of knowledge. My next car l m going to buy with them also and with Tatiana of course. If you are looking for a good price and a solid car go there and ask about Tatiana. Mike volvo v v90 cross country

i recently had a 2023 for explorer it was a good truck never a problem but not a comfortable as the jeep grand Cherokee l front seating is amazing no issues at all i did my research and made sure i bought one with the German transmission its a good idea to check that only thing i can say on the down side seam to be a little under powered but i can live with it decent milage 20 around town.

I purchase a 2019 Qx60 my experience was very very good sale person Thomas pates did a wonderful job to get me in this car everyone was helpful I will purchase another vehicle from there I am from Milwaukee thanks carwise

I,ve had several Jeeps and Subarus and Chevys and my Compass Latitude 4x4 is as good as any for around the city and my freeway trips. Better than the Subaru for the highway and offroad. I feel safe. posted this as i feel some people are harsh and wrong about Jeeps. Do the required oil and transmission services as requested.

quite impressed with staff and facilities. great experience all around. staff was accommodating and courteous. i wanted to wait and drive it for some time before i gave an honest review. i have been driving it 4 about a month now with no issues. great deal and fine vehicles. i love my sea-frost green jaguar! even got a free wash/detail 2 boot. i would one hundred percent recommend chicago cars us to anyone looking for a used/exotic vehicle. thank u. b well...

The '03 TJ's hit the sweet spot in the '97-'06 line. They were the last major revision, especially with the 'TUPY' cylinder head, and parts revisions in '04-'06's, well, have issues. 'TJ' means (last) True Jeep. The 4.0L '03's are special. You ride in a car, you drive in a Jeep.

Edgar Gonzalez has been the best Service Representative that I have ever experienced with this dealership. He is truly a professional at customer service, knowledgeable about the vehicles and warranties. He was awesome in the repair of my Ram truck. Thank you for hiring this gentlemen, a true professional!!

Incredible vehicle. Especially if you put a manufacturer 3 inch lift on it and aftermarket wheels and tires and running boards. A total beast if you can’t afford the Renegade or if you are too upside down on your trade. If you don’t know the Jeep go get one. It’s life-changing.