Used 2020 Jeep Grand Cherokee for Sale nearWinnipeg, MB

How much does the 2020 Jeep Grand Cherokee cost?

Prices have softened 12.37% compared to this time last year, making it a favourable time to shop this model year.

There are 543 listings available, which suggests you have a reasonable amount of inventory to compare.

Is the 2020 Jeep Grand Cherokee a good car?

Yes — it earns a 4.58/5 user rating and a 6.33/10 expert rating. The model scores 8/10 across Look and feel and Technology.

Owners consistently praise its comfort, performance, and luxurious features, and they also like the powerful engines and ride quality. The Grand Cherokee’s stylish design and off-road capability are central to its appeal, and it suits you best if you want a traditional SUV character rather than a crossover feel.

The trade-offs are clear: advanced safety features are not standard, and value for money is a weak point. Even so, the market still shows 31.7% of listings as good or great deals, which helps offset some of that concern.

Is the 2020 Jeep Grand Cherokee reliable?

Owners rate it 4.58/5, a strong signal of long-term satisfaction.

Owners describe it as dependable in the ways that matter most to them, especially for comfort, performance, and the ability to count on its strong powertrain and ride quality. The expert evaluation also points to a traditional SUV that behaves consistently and remains capable in daily use and off-road situations.

That said, used buyers should still watch for wear-related issues tied to an older platform, especially if the vehicle has seen hard use or infrequent maintenance.

What should I look for when buying a used 2020 Jeep Grand Cherokee?

Key things to evaluate:

• Trim level: The Limited X adds an 8.4-inch touchscreen, navigation, Bluetooth, Apple CarPlay, Android Auto, SiriusXM satellite radio connected services, and a more upscale appearance, while higher trims bring more premium materials and equipment. Base versions are less richly equipped, and the safety package is not fully loaded on every trim.
• Powertrain: The standard setup is a 295-horsepower, 3.6-litre V6 with an eight-speed automatic transmission. If you want more muscle, V8 options are available, including the 5.7-litre Hemi, the 6.4-litre Hemi in SRT, and the supercharged 6.2-litre V8 in Trackhawk.
• Safety package: ProTech I is standard and includes a reversing camera, parking sensors, blind-spot monitoring, and rear cross-traffic alert. ProTech II adds low-speed forward-collision warning, automatic emergency braking, lane-departure warning, lane-keeping assist, and automatic high-beam headlights. Advanced ProTech II adds full-speed forward collision warning, adaptive cruise control with stop-and-go, semi-autonomous parking assist, and rain-sensing wipers.
• Infotainment: The Limited X uses an 8.4-inch touchscreen with navigation, Bluetooth, Apple CarPlay, Android Auto, and SiriusXM satellite radio connected services. A 4G LTE WiFi data plan is available, and some versions can be equipped with a 19-speaker Harman Kardon audio system.
• Fuel efficiency: The standard V6 returned 11.3 L/100 km in combined driving according to Natural Resources Canada, and the test vehicle recorded 12.1 L/100 km.

Which 2020 Jeep Grand Cherokee trim should I buy?

The 2020 Jeep Grand Cherokee is offered in 4 trim levels: Laredo, Limited X, SRT, Trackhawk.

Here's the short version:

• Laredo: This is the entry point, so it makes sense if you want the Grand Cherokee’s core styling and capability without paying for the richer equipment found higher up.
• Limited X: This is the best-value choice if you want the strongest mix of equipment and everyday usability, including the 8.4-inch touchscreen, navigation, Apple CarPlay, Android Auto, and a more premium look.
• SRT: Choose this if you want serious performance, since it brings the 6.4-litre Hemi V8 and a more track-focused character.
• Trackhawk: This is the extreme performance pick, with the supercharged 6.2-litre V8 and the most aggressive hardware in the range.

ProTech I is standard on all trim levels, while higher trims can add more advanced driver-assistance features through ProTech II and Advanced ProTech II.

Is now a good time to buy a used 2020 Jeep Grand Cherokee?

This looks like a moderate, selective buyer’s market, so you can shop carefully and still find worthwhile listings.

• Deal availability: 31.7% of listings are priced as good or great deals.
• Inventory: There are 543 listings available.
• Price trend: Prices have softened 12.37% compared with last year.

If you find a listing below $26,807 CAD, that's toward the low end of the year-round range and worth acting on quickly.

What is the 2020 Jeep Grand Cherokee's resale value?

The current average of $26,973 CAD sits slightly below last year's $30,780 CAD.

That softer pricing can help you as a buyer now, but it also means a future seller may need to be realistic about expectations. If you buy at the current average, there is less room for a quick profit later unless the market tightens again. The Grand Cherokee’s broad appeal and strong feature set should still support demand, especially for well-equipped examples.

Vehicles with strong owner satisfaction ratings, like this model year's 4.58/5, tend to retain buyer demand, which supports resale value over time.

Is the 2020 Jeep Grand Cherokee safe?

The Grand Cherokee earns a four-star overall rating from NHTSA.

It earns a 3/10 safety score from our experts.

Jeep’s ProTech I suite is standard on all trim levels and includes a reversing camera, parking sensors, blind-spot monitoring, and rear cross-traffic alert. ProTech II adds low-speed forward-collision warning, automatic emergency braking, lane-departure warning, lane-keeping assist, and automatic high-beam headlights, while Advanced ProTech II adds full-speed forward collision warning, adaptive cruise control with stop-and-go, semi-autonomous parking assist, and rain-sensing wipers.

The main caveat is the crash-test performance: IIHS gives it a Marginal rating for driver protection and a Poor rating for front passenger protection in the small overlap frontal-impact test, and the headlights rate Poor unless you upgrade to the Acceptable HID headlights in the Premium Lighting Group.

Should I buy a 2020 Jeep Grand Cherokee or consider a different year?

If you're weighing the 2020 against nearby model years, here's how to think about it:

Choose the 2020 if:

• 31.7% of listings are priced as good or great deals.
• Price trend: Prices have softened 12.37% compared with last year.
• Owners rate it 4.58/5 — a strong satisfaction signal.
• It remains an appealing but flawed choice, with strong style and off-road capability.

Consider the 2021 if:

• At $29,699 CAD, the 2021 costs more than the current year's $26,973 CAD average.
• It is the final version before the redesigned model arrives, and it keeps the familiar two-row format.

The bottom line: If you want the better value today, the 2020 is the smarter buy because pricing has eased and inventory is decent. If you are willing to spend more for the last year of the old-generation formula, the 2021 is the cleaner choice for buyers who want to stay with the familiar two-row Grand Cherokee before the redesign.

These recommendations are based on CarGurus' proprietary market data from September 22, 2026, CarGurus experts' opinions, and generative AI.