Shopping a used Grand Cherokee is harder than it looks, because the nameplate has been around long enough that two vehicles wearing the same badge can be a decade apart in design. Somebody tells you they love theirs, you go looking, and you find yourself comparing things that have almost nothing in common except a name and seven slots in the grille.

Shopping already? Browse our new Jeep Grand Cherokee inventory in Portage la Prairie.

The useful question is not really which single year is best. It is which years brought real change, because those are the lines where the price you pay and the vehicle you get stop matching up. Have a look at the used vehicles on our lot while you read this, because the year splits below are exactly how we sort them when they come through on trade.

Everything year specific below is checked against Jeep and Stellantis announcements. Where we could not confirm something, we say so instead of guessing.

Key Takeaways

• The big line is the 2022 redesign. The 2022 Grand Cherokee is a fifth generation vehicle on an all new architecture. Anything 2021 or older two row is the previous generation. That single split matters more than any other year to year change.
• Within the older generation, 2014 is the meaningful step up. For 2014 Jeep put an eight speed automatic behind all three engines, added the 3.0 litre EcoDiesel V6, and quoted best in class towing of 7,400 pounds with an improved 44.1:1 crawl ratio.
• 2021 is the odd year worth understanding. That is when the three row Grand Cherokee L arrived as an all new vehicle, while the two row carried on in its previous form. Two very different vehicles, same showroom, same model year.
• Canadian cars carry extra standard cold weather content. Jeep has made heated front seats, a heated steering wheel and remote start standard from Laredo up on Canadian Grand Cherokee models, which is worth knowing when you are comparing a local car to something imported from a warm state.
• Buy the specific vehicle, not the model year. Two 2018s with the same kilometres can be in completely different condition after eight prairie winters. Service history and an inspection beat a year off a list every time.

The Generation Split Is the First Decision

Before you look at a single listing, decide which side of 2022 you are shopping.

The 2022 Grand Cherokee was an all new fifth generation vehicle. Stellantis introduced it as the most technologically advanced and most luxurious Grand Cherokee yet, on a new architecture with a new interior and a new plug in hybrid option. In Canada the launch lineup ran Laredo, Altitude, Limited, Overland, Trailhawk, Summit and Summit Reserve.

The engine choices at that launch were a 3.6 litre Pentastar V6 at 293 horsepower and 260 lb ft, rated to tow 2,812 kg (6,200 lb), a 5.7 litre V8 at 357 horsepower and 390 lb ft rated to tow 3,265 kg (7,200 lb), and the 4xe plug in hybrid pairing a 2.0 litre turbocharged four with two electric motors for 375 horsepower and 470 lb ft, about 40 kilometres of electric range, and 2,720 kg (6,000 lb) of towing.

Everything two row from 2021 back is the previous generation. It is a good vehicle and it is a lot cheaper, but it is a different thing. If your budget puts you at the top of the old generation or the bottom of the new one, that is the real decision in front of you, and it is worth driving both back to back before you commit.

For a closer read on how the two row and three row compare, our post on the Grand Cherokee and the Grand Cherokee L breaks that out.

2014: The Year the Old Generation Got Good

If you are shopping the previous generation, 2014 is the year to start from rather than reach below.

Jeep announced for 2014 that all three Grand Cherokee engines moved to an eight speed automatic, which improved fuel economy, acceleration and shift smoothness in one change. The same announcement introduced the 3.0 litre EcoDiesel V6, quoted best in class towing of 7,400 pounds, and an improved crawl ratio of 44.1:1.

That combination is why a 2014 or newer example of the old generation drives noticeably better than an early one. The eight speed is the change you feel every day. On a 2011 to 2013 car you are living with the older transmission, and the gap is real enough that we would rather sell somebody a higher kilometre 2015 than a low kilometre 2012 in most cases.

The EcoDiesel is a different conversation. It tows well and it is efficient, but diesel ownership carries its own maintenance and its own repair costs, and on a vehicle this age you want documented service history before you take that on. If a diesel Grand Cherokee interests you, ask us to go through the specific car's history with you rather than buying it on the badge.

2021: Read the Listing Carefully

2021 is the year that confuses shoppers, and it is worth slowing down on.

That is when the Grand Cherokee L arrived, the first three row Grand Cherokee ever built. Stellantis launched it as an all new vehicle out of the Detroit Assembly Complex at Mack, a plant the company invested $1.6 billion US into and staffed with 3,850 new jobs specifically to build it. Meanwhile the two row Grand Cherokee continued in its previous form for 2021.

So a 2021 Grand Cherokee L and a 2021 Grand Cherokee are not the same vintage of vehicle at all. The L is effectively the new generation with a third row. The two row is the old one in its final year. If you are searching by model year alone, you will see both at similar money and think you are comparing like for like. You are not.

This is also where the Canadian content note matters. On the Canadian 2021 lineup, Jeep made heated front seats, a heated leather wrapped steering wheel and remote start standard from Laredo up. A Canadian market car is genuinely better equipped for here than an equivalent American one, and that is worth a premium on a February morning in Portage.

What Actually Wears Out Here

This is the part a national buying guide cannot write for you, so here is what we see on trades.

Rust is the honest first item. Manitoba puts salt and brine on the highway for months, and the underside of a ten year old vehicle out here tells a very different story than the same vehicle from Alberta. Look at the rear wheel arches, the rocker panels, the brake and fuel lines, and the exhaust. A clean body with a scaly underside is common and it is the thing that decides whether a vehicle is worth buying at all.

Air suspension is the second. The height adjusting suspension is a genuinely good system and it is a repair cost when it ages. Cycle it through its settings on the test drive and make sure it lifts and settles properly. If it has been left alone or the compressor sounds like it is working hard, factor that in.

Cold start behaviour is the third. Anything that is marginal in October is a no start in January out here. Get the battery and the charging system checked before you buy, not after.

And the ordinary stuff still applies. Tires with real tread, brakes with life left, and a service record that shows somebody actually did the maintenance. Our service department will go through a vehicle you are considering, including one you found somewhere else.

On recalls, do not take anyone's word for it. Run the VIN yourself. Our post on how to check recalls on a Ram or Jeep by VIN walks through it, and it takes about two minutes.

Where the New Ones Sit Now

Worth knowing what the current car is, because it sets the ceiling your used shopping is measured against.

For 2026 the Grand Cherokee picked up the new Hurricane 4 Turbo, rated at 324 horsepower and 332 lb ft, with a 12.3 inch infotainment display, refreshed exterior styling and a simplified trim walk. Towing with that engine is up to 2,812 kg (6,200 lb). The 3.6 litre V6 carries on lower in the range, and the 4xe plug in hybrid continues with 470 lb ft.

Sometimes the math on a new one works better than people expect once you put a trade against it and look at what the payment actually is. If you want to test that, get a number on your current vehicle with our instant cash offer tool, then compare it against the new Grand Cherokee inventory or the three row Grand Cherokee L. If the used one is still the better buy, we will tell you that.

For what the current generation will actually pull, our post on Grand Cherokee towing capacity has the numbers by configuration.

FAQs

What is the best year for a used Jeep Grand Cherokee?

There is no single best year, but there are two lines that matter. Shopping the current generation, 2022 and newer is an all new vehicle on a new architecture. Shopping the older generation to save money, start at 2014 or newer, because that is when the eight speed automatic went behind all three engines and towing was quoted at 7,400 pounds. Beyond that, condition and service history matter more than the year on the listing.

What is the difference between a 2021 Grand Cherokee and a 2021 Grand Cherokee L?

They are effectively different vehicles sold in the same year. The Grand Cherokee L was all new for 2021 as the first three row Grand Cherokee. The two row Grand Cherokee continued in its previous generation form that year. Read the listing carefully, because at similar money you may be comparing a brand new design against an outgoing one.

Is a used Grand Cherokee a good vehicle for a Manitoba winter?

It can be a very good one, with the caveat that condition decides it. The Canadian lineup has carried standard cold weather content from Laredo up, including heated front seats, a heated steering wheel and remote start, so a Canadian market car is better suited to here than an imported one. Check the battery, the block heater if fitted, and the underside for corrosion before you buy.

Should I buy the EcoDiesel?

Only with documented service history. The 3.0 litre EcoDiesel arrived for 2014 and it tows well and returns good fuel economy, but diesel maintenance and repairs cost more than gas, and on a vehicle of this age that history is the whole story. Bring the specific vehicle to us and we will go through it with you honestly.

How many kilometres is too many on a used Grand Cherokee?

Kilometres alone is the wrong measure out here. A highway driven vehicle with 180,000 km and full records is frequently a better buy than a 110,000 km one that sat outside and got the oil changed when somebody remembered. Look at the service history and the underside first, then the odometer.

Should I buy new instead?

Sometimes, and it is worth actually checking rather than assuming. Once you put a real trade value against a new one and look at the payment, the gap is often smaller than people expect, and you get full warranty instead of somebody else's maintenance decisions. Ask us to run both numbers side by side.

The Bottom Line

The Grand Cherokee rewards a shopper who knows where the lines are. Get to 2014 or newer if you are buying the older generation, understand that 2022 started something genuinely new, and read a 2021 listing twice before you assume you know what you are looking at.

Then stop shopping the year and start shopping the vehicle. Bring the one you are considering to us, or come look at what we have on the used lot, and we will give you the straight read on whether it is the right one to put a Manitoba winter through.

Tyler Dunn, Dunn Ram Trucks, Portage la Prairie