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

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.

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 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.

TY was and amazing help to me! He is in fact a real like rockstar who made this complicated process the easiest it could’ve been!

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!

Wide selection and no haggle are a plus over other dealerships. I like being able to see how many different makes and models. CarMax is the only place I will shop

  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.

Napleton of Calumet City, IL is a great place to shop for a new or used vehicle. Their Staff is very polite and professional. I would highly recommend them if you're looking for a new or used vehicle. They go above and beyond what's expected of any dealership.

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!

Alexandra help us solved our problem, We had to sell Grandmas Car without a title in short time in town. They gave us what we wanted without a title in a few hours at CarMax. This was an unimageable process that Alexandra help us through....Alexandra was Calm with Great Compassion. We Appreciate Alexandra and CarMax Thanks again..

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

Mike R was amazing. He even traveled to Chicago to bring our car to a different locations so we could see it. I would highly recommend this location.

Mike at Bronco Motors Original made the car buying process simple and easy. Being a first time buyer not having much of an idea, Mike did a great job making sure everything I needed to do was clear and precise. I appreciate everything done by him and the experience was quick and simple. The jeep runs so well, it has plenty of space to transport everything I need and is overall an awesome first car. Great experience overall. Thanks again Mike!

Ovdio gracias si muy bien 100 percent awesome job 3 car there 5 m0re ovi

The 2019 Grand Cherokee Limited was the Jeep I had my eye on for a while. I've owned a 2012 Laredo X, and a 2018 Limited Anniversary/Heritage Edition. I was specifically looking for Limited trim without the 20" rims, although, I love the look of the Altitude versions, I just didn't really care/want to deal with less side-wall, nicer-looking rims. I avoided the Overland and Trailhawk because of the air-suspension. Overall the interior is fine, it's comfortable and familiar for me, since I've owned them before, but that's also the only issue/complaint I would have. The interior is updated from the 2012, however, basically it's a very light update, U-Connect, Gauges, Shifter, and possibly a few other items here and there. But essentially, the dashboard is the same dashboard I've seen since 2012. While owning the previous (2) I never experienced any mechanical issues that left me stranded. One had a weird issue with blowing lights in the tailgate, but it would just randomly decide to burn out, replace one it would blow another. No other major issues. The 2019 leather on the steering wheel feels smooth and buttery like they always have. The suspension feels great, still solid and tight. Brakes are strong and grippy, pedal feel is nice and firm. So far I'm super satisfied with this Jeep, I got the perfect combination of all the features I wanted, Memory Seats, Sunroof, power trunk, heated-seats and wheel. Not sure if I'd be willing to sell this one and get a newer model, but, I'd possibly get another WK2.

I visited to look at a 2013 Sonata and ultimately decided to buy a 2022 Palisade for my whole family. I am impressed by the courtesy and service they offer. It is on another level. I will strongly recommend them to any friends or family members. This is their new location, and the staff, vehicle selection, and prices are excellent.

Very easy to drive nice looking car very comfortable love the third row seat and the ease of getting to it the seats fold up and you have easy access

Awesome service from Jose!!! Very patient and kind. Explained every detail. All dealerships need a Jose!

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.

Their excellent service and support truly made me feel confident and well taken care of throughout the entire process. From the moment i arrived, everything was handled with professionalism and genuine care. It’s rare to find a place where you feel both valued and understood as a customer, but that’s exactly the experience i had here. Once again, thank you, Zee—your outstanding service truly stood out.

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.

This is car number 8 with Midway Dodge. This is the only place we shop. We always receive great service from everyone here. Thank you for the great service especially Money Carlos

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.

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.

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

we bought 4 different vehicles in total from them, Frank and Jennifer are the best.

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

Best Car Dealership. Ask for Jimmy Best Use Deals on the market They let you inspect and drive the car. Take it to shop before purchasing Thanks guys

Very nice ride for the type of vehicle it is Nice and roomy on the inside. Leather seats are very easy to care for. Very low maintenance.

Now in my 6th year with my 2017 and still like it. My complaints are simple. Needs larger fuel tank, better gas mileage considering its size and engine, would prefer manual transmission, and get rid of the xxxx engine shut off function. Love the size, comfortable, still seems solid. My only repair was replacement of the satnav unit that crapped out.

Sean was amazing! He truly went above and beyond to make everything happen for us. He was patient, honest, and worked hard to get us exactly what we needed. Highly recommend him to anyone looking for a great car buying experience!

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.

My wife and I live in Texas. So obviously there are thousands of dealerships from here to Chicago but after talking to DJ, we decided to take the drive out here. We had such a great experience with DJ. If you are looking for a stress free car buying experience go see DJ at Midway Dodge

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 !

Frank and Jennifer are outstanding to work with. This was my 2nd vehicle purchase in just over a year with MCA. Most recent was a Nissan Rogue, my wife absolutly loves it. I purchased a Toyota Corolla for myself little over a year ago. No pressure, good prices, excellent service, and Frank worked hard to get me a great interest rate. I'm usually a very hard person to deal with to car salemen because I drill them when they try there side gimicks. Frank is straight forward,low pressure, and just goes above and beyond to give you his best deal. Bought many cars in Michagan City & Laporte from dealerships over the years. Frank and Jennifer make a great team and treat you like family. Without a doubt this is now my go to dealer.

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.

2017 GC Limited 4WD. Bought it 3 years ago with 53k miles and now approaching 108k miles. When we bought it, we went to fill the tank for the first time and the gas pump kept shutting off. Turns out there was a known issue with the fuel filler neck assembly. The selling dealer replaced it under warranty and we literally didn't have another issue until 100k miles. At 100k miles took it in for new spark plugs, which is normal maintenance, and found the radiator leaking. The new radiator was not cheap. Have not had any other issues, just replaced the factory original brakes, they made it almost to 108k! We live in Minnesota and this vehicle is an absolute beast in the snow. Put it in snow mode and it is very stable and feels unstoppable. It is a comfortable long distance cruiser and gets decent mileage on the highway, between 24-27mpg. The UConnect system is very easy to use, and the nav is pretty good, but the whole system operates quite slowly. That's a minor complaint I think. Overall we are pretty happy with our WK2.