Used Jeep cars for sale near Winfield, IN under $19,989

I can always count on my service needs being met. Quick Lane is convenient. My last service Was completed on time and corrected.

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.

A fair price was advertised for the used car we were looking for. It made it worth the trip for us to buy from Pearl. Nick and Chris were great to deal with. Very friendly and honest. The whole experience was low pressure and hassle free. The process was quick and easy.

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 have bought a few vehicles from Team, they do a good job with process to keep things moving, worked with Rick and Ritchie , like my new Tacoma.

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.

I want to thank Kristen for being so AWESOME! He professionalism was so much appreciated throughout my buying experience. She continued to reach out and help/support me in anything I needed after my purchase was made. Thank you so much Kristen. Keep up the good work!

Bought this 2022 Compass Trail Hawk new for my wife. Earlier this year (2025) we landed a sweetheart deal on a new 2024 Wrangler Sport S. Guess who inherited the Compass ? I stepped down from a Grand Cherokee but I have no regrets. It has had a few electrical teething issues but all have been resolved and have not come back. The handling and fuel economy are much better than the Grand Cherokee. There are only 2 downsides..........the size of the gas tank (13.5 gal vs 24.5) and the cargo space behind the 2nd row seats. I have easily adapted to both ! I want to give a shout-out to our local dealership, Tri-City CDJR. Start to finish, an excellent place to purchase and maintain our Jeeps. BRAVO ZULU !

I was in and out in less than an Hour. Everyone was very pleasant, the paperwork was explained in detail. They allowed me to leave my other vehicle there until someone took me to pick it up. From the time I entered ti the time I left I felt very comfortable.

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

I want to thank Joe Collins for the wonderful service I received today. From the time I arrived I was welcomed with a smile and knowledgeable service. Joe and the technicians that serviced my Caravan today I want to say Thank you. Someone asked me why I bring my vehicle here for service this is why! I would recommend Castle Chrysler Dodge Ram of Chesterton. I have been a customer now for over 5yrs. and they have always been top notch. You have earned a 5star from me. That's why I'll always return. Happy Holidays to the entire staff and especially to Joe Collins for all your kindness 🥰

  I have the Trailhawk trim, the serious off-road version.  Finally, a car that I can confidently drive in and out of rough construction sites, and not be afraid that I'll break it or get it stuck.   It is possessed by a powerful spirit of wanderlust, and frequently demands that I take it on drives just to see places it hasn't yet been, preferably places that normal cars cannot go.   If Don Quixote de La Mancha lived in our time, he would surely drive a vehicle like this one; a vehicle truly fit for a modern Knight Errant.   I didn't know until a few days after I bought it, and I don't think the dealership knew either, but this one has about a 2" aftermarket lift, and slightly larger tires than stock.

All good, salesman was very good, very quick process, and being local, will be very convenient

I bought a 2023 Jeep compass Latitude Lux. Wish they come with all the other specs in driver assists like wireless charging, power tailgate, dual zone AC control, adaptive cruise control etc.

5 stars – Honest, efficient, and the reason I came back This was my second time working with Josh Hendrix, and I specifically came back because of how straightforward he is. We were buying a car for my daughter, and I appreciated that Josh didn’t push, didn’t upsell, and didn’t waste our time. He gave us a fair offer from the start and made the process easy. After dealing with salespeople at other dealerships who overtalk or dodge questions, Josh is someone I trust. If you’re buying a car, especially for family, he’s the one to work with.

Vehicle is beautiful, but has cracks on the rims and heated seat features do not work or the spotlights Oil change was not done, this is why I wanted to go through a dealer than a private party, for maintenance

I had the Works maintenance service done. Susan my service rep was great! I appreciated her checking on me and letting me know what was happening with my Escape and how much longer it will be till done.

I've added aftermarket exhaust and a computer chip and the roar pedal also KNN air filter and bigger tires 35 so far it is a lot of fun to drive

Very friendly and efficient place. They made a stressful process so easy. I am happy that I decided to go with Chicago Motor Credit.

In my many years of car driving and ownership, I have rarely had a better vehicle than my 2019 Jeep Compass Latitude. It has been reliable, comfortable, fun to drive and, for its' size and type, very good on gas. In April, I will have been driving "Lattie"for 5 years. My upkeep has been minimal. She is pretty and still looks new. This vehicle is such a pleasure to drive. Handling and response are excellent. Controls are super easy to manage and absolutely love the heated seat and steering wheel. On a long trip, it is very comfortable (yes, I have ridden in the back seat, too) and fuel economy was just great...fully loaded with air-conditioner on and travelling at highway speeds gave me 30+ mpg. Really can't complain. My Neon didn't do any better. This is a great vehicle. Oh, and I had leased it new, and purchased it when the lease was up..that's how good this car is!

Great experience, Friendly Service and Sales team. This is the second vehicle I purchased from this Dealership. My salesperson was awesome throughout the entire process. Thank you Brittany K.

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!

It was very good. Everyone was friendly and professional. The whole buying process was quick and easy. We had bought vehicles there before and will go back again

We purchased our 2014 Grand Cherokee Overland new and after 11 years and almost 150,000 miles it easily the BEST vehicle we have ever owned. It is comfortable, delivers reasonable mileage, is quiet, well built, incredibly durable and looks as good today as the day we took delivery.

they were very patient did not push me into anything the service was quick the only thing they talked me into was a extended warranty.. hope I never need it and hope it is as good as they say Enjoy

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.

Ashley did an excellent job presenting the vehicle and making sure we understood all the many options.

Great little SUV, nice options as good as a more expensive luxury car. Smooth ride and very comfortable. I'd recommend this Jeep to anyone wanting a smaller SUV

Great person he helped my whole family. What a blessing to have him around. I came in and left out with a miracle

Car was perfect and price was under budget for what I was looking for love the feel of the ride and the seats are very comfortable for a woman, my husband is a big guy and he does not fit too good.

Everything went perfectly. The car ran smoothly, and I was very happy with the process. It was quick, easy, and completely hassle-free. Overall, a flawless experience. Highly satisfied..

I bought mine used..Love it, but sad to hear the model has been discontinued..Mine is pretty basic...not many extras to break...decent gas mileage, running great on E15, too.

Working with Castle Jeep was simply awesome. I have never had a better experience at a dealership. Josh and Tony did such a great job working with me. I don’t have enough good things to say about them.

I purchased this Jeep brand new in 2012 as a 2013 Model, I have since put 150,000 miles on. It is a Jeep and can get a little uncomfortable on long highway drives. I took this on a 3 week coast to coast road trip across the US I would know. It does a great job towing my 20foot i/o boat to and from the lake, but wouldn't recommend long trips with that much to tow. Maintenance has been astonishingly low, the only things I needed was regular oil changes, brakes, and a radiator leak that was covered under warranty. This is one of the best all around vehicles, top down cruising in the summer and 4x4 for the snowy PA winters.

Our salesperson was Faye. She was laid back and not pushy. I really appreciate her patience with us. We gave her a price point and she helped us to reach it. I wish all sales people were as professional and personable as she is. We would definitely recommend her and your staff for our future needs.

I have had my 22 High Altitude for about 4 months now and the only issue(s) I find are the following: MPG is not as advertised, it's not that great. It's around 24 average, I am about 50/50 city/highway driving - It's fine. It DOES ride like a Jeep - so it's not as "luxurious" as your higher end cars, but YOU BOUGHT A JEEP - The last snow storm we had in Cleveland was about 10" in 2 hours - No problem, even with 235/45/19 tires - Would be way better with not so wide tires. It's slow. Who cares? Are you driving in the F1? Nah - It's plenty. Interior is baller. Infotainment is great, comfortable. Heated steering wheel is a plus. IDK - I read these reviews and everyone is so picky - It's a nice ride. If you find you like it, give it a shot.

Bought my car here , Dan was exceptionally helpful. definitely recommend. Very nice selection of cars.

Bought one for my son for college. Had 108K, now as 190K. Can't complaint. Safe, reliable and very comfortable. Did have to replace the oil cooler assembly, but that's a given on a 3.6. Other than that, tires, brake pads, the usual. It's been a winner.

Our first service to KIA. It was a great experience Jacob is very professional and helpful. Definitely, I?ll recommend this dealers to my friends and family. Thank you!

I never thought I'd own a Jeep in my lifetime, then five years ago I bought a used 2014 Jeep Patriot and was amazed by its fuel economy and reliability for a mid-size SUV. Then three months ago my sister needed a car, and I passed the Patriot along to her, so I began doing research to buy another used car for myself and found the 2014 Jeep Compass. Now I'm the proud owner of not one but two Jeeps! I fell in love with it because of its looks as it is "less boxy" than the Patriot and the interior is basically a replica of a car I'm already used to driving. Find it a little bit roomier than the Patriot, love the top of the gate spoiler and the headlights design as well as the focused (foglights?). I can carry a ton of stuff in the back specially since I added the retractable cargo cover for privacy and safety. I definitely recommend this crossover SUV, it delivers a ton for its value. Definitely money well invested.