10 of the Best Chrysler Cars on the Used Market Right Now
Chrysler has always been a brand that does its own thing. For over a hundred years, they’ve jumped between high-end luxury and building the minivans that basically saved the American family road trip. Because they’ve tried so many different things, the used market is full of interesting options. You can find vehicles that still have plenty of life left, offering real character and capability for a lot less than you’d pay for a new model.
Around here, we know that the “best” used Chrysler isn’t always the newest one on the lot. It’s about matching the car to how you actually drive. Here are 10 models from the Chrysler family tree that our team still recommends today.
1. Chrysler Imperial: The Standard of Mid-Century Opulence
If you’re looking for that classic “land yacht” feel, the Imperial is the heavyweight champ. It was built for one thing: being the biggest, most comfortable car on the block. With all that chrome and the massive hood, it’s a head-turner. The Pro-Tip: Don’t try to make this your daily driver in Morgantown traffic. These are for weekend cruises. When you’re shopping, look for one that has all its paperwork—a well-documented history is worth more than a “cheap” price on a car that’s been sitting in a field.
2. Chrysler New Yorker: The Classic Cruiser
The New Yorker nameplate was around forever for a reason. It was the standard for what a big American sedan was supposed to be: quiet, heavy, and smooth. Modern cars are built to be stiff for “sporty” handling, but the New Yorker goes the other way. If you want a ride that just eats up the bumps on the highway without feeling harsh, this is a great classic choice.
3. Chrysler Cordoba: The Personal Luxury Icon
Back in ’75, the Cordoba was Chrysler’s answer for people who wanted luxury but didn’t want a four-door tank. It’s a coupe with a lot of attitude. You don’t see many clean ones left, but when you do, they really stand out. Our advice? If you find one, check the frame and the mechanicals first. You can always fix up an interior, but a solid chassis is what makes a Cordoba worth keeping.
4. Chrysler LeBaron Convertible: Open-Air Accessibility
Looking for a convertible that won’t break the bank? The late 80s and early 90s LeBaron is an easy entry into the world of top-down driving. They aren’t complicated to work on, and parts are still fairly easy to find compared to European imports. When we see these in our shop, the first thing we check is the top motor and the seals around the windows. If it’s dry inside, the rest is usually straightforward.
5. Chrysler Crossfire: The Enthusiast’s Outlier
The Crossfire is a bit of a weird one, but in a good way. It shares a lot of its DNA with Mercedes-Benz, which means it handles much tighter than most Chryslers from that time. It’s a fastback that’s built for the driver, not for hauling groceries. It’s a great pick for someone who wants something unique and mechanical under the hood.
6. Chrysler 300: Unmistakable Road Presence
You can’t mistake the 300 for anything else. That big grille and the chopped-roof look give it a presence on the road that most new sedans just can’t match. It’s actually got a ton of room inside, too. Whether you go with the V6 for the commute or find one with a Hemi for the power, you’re getting a car that still looks like a million bucks in a parking lot.
7. Chrysler PT Cruiser: The Utility Wildcard
Forget what people say about the “retro” look. If you need a cheap car that can fit a mountain of gear, the PT Cruiser is hard to beat. The roof is high, and you can pull the seats out to turn it into a mini-van. For a budget-friendly city car that’s actually useful, it’s one of the best values out there.
8. Chrysler Aspen: The Overlooked SUV
The Aspen is a sleeper in the SUV market. It’s basically a Durango but with a nicer interior. If you need to tow a trailer or haul eight people and don’t want to pay the massive prices for a brand-new three-row SUV, this is the “smart” buy. We always tell people to look closely at the service history on these—a well-oiled Aspen will run circles around a neglected newer SUV.
9. Chrysler Town & Country: The Family Gold Standard
The Town & Country is the original family hero. Even with all the new tech in modern vans, the T&C is still a workhorse. Between the power doors and the massive amount of room, it just makes life easier. It’s not about being flashy; it’s about getting the job done. If you need a reliable hauler for the kids and their gear, this is the gold standard.
10. Chrysler Pacifica: The High-Tech Evolution
The Pacifica is where Chrysler is at right now. Since 2017, it’s been the van to beat. It drives more like a car than a bus, and the Stow ‘n Go seating is still the best invention in the segment. If you want a modern, safe, and reliable daily driver that’s ready for anything, the Pacifica is the most logical choice on this list by a mile.
No matter which one you’re looking at, the “best” used Chrysler is the one with a fat stack of service records. The badge on the back doesn’t matter nearly as much as how well the previous owner took care of it. Before you buy, bring it by a shop you trust for an inspection. A car with a solid history will always be a better deal than a “bargain” that’s hiding a bunch of mechanical issues.