Used 2020 Jeep Grand Cherokee for Sale nearWinnipeg, MB

How much does the 2020 Jeep Grand Cherokee cost?

Prices have softened 16.68% compared to this time last year, making it a favourable time to shop this model year.

There are 591 listings available, which suggests a healthy amount of inventory for shoppers to compare.

Is the 2020 Jeep Grand Cherokee a good car?

Yes — the 2020 Jeep Grand Cherokee earns a 4.6/5 user rating and a 6.3/10 expert rating. The model scores 8/10 across Look and feel and Technology.

Owners consistently praise its comfort, performance, and luxurious features, and many also like the powerful engines and impressive ride quality. The overview points to broad appeal for buyers who want a vehicle that can handle rougher terrain without giving up everyday usability, while the expert review also highlights its stylish design and off-road capability.

The trade-offs are clear: advanced safety features are not standard, and value for money is weak. Even so, the market still shows 33.8% of listings as good or great deals, which gives you some room to shop selectively.

Is the 2020 Jeep Grand Cherokee reliable?

Owners rate it 4.6/5, a strong signal of long-term satisfaction.

The owner summary points to a vehicle that feels comfortable, powerful, and luxurious, with many drivers describing it as a model they enjoy living with over time. It also suggests the Grand Cherokee can be dependable in daily use, especially when you value strong performance and a refined ride.

The expert review adds that the Grand Cherokee’s powertrain delivers satisfying acceleration, and its traditional SUV character remains a core strength. Jeep also includes useful ownership-friendly touches such as a 4G LTE WiFi data plan and a well-regarded infotainment system.

For used buyers, the main long-term risk is that age-related wear and uneven build quality can matter more as mileage climbs.

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

Key things to evaluate:

• Trim level: The base setup includes ProTech I, which gives you a reversing camera, parking sensors, blind-spot monitoring, and rear cross-traffic alert. Higher trims add more equipment, and the Premium Lighting Group brings better headlights.
• Powertrain: You get a standard 295-horsepower, 3.6-litre V6 with an eight-speed automatic transmission. The review also notes available V8 options, including the 5.7-litre Hemi, plus performance-focused SRT and Trackhawk variants.
• Safety package: ProTech I is standard on all trim levels, while 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: In Limited X trim, Uconnect includes an 8.4-inch touchscreen, navigation, Bluetooth, Apple CarPlay, Android Auto, and SiriusXM satellite radio connected services. A 4G LTE WiFi data plan is available, and Off-Road Pages add useful trail information.
• Fuel efficiency: The test SUV returned 11.3 litres per 100 kilometres in combined driving, while the test vehicle itself saw 12.1 L/100 km.

Which 2020 Jeep Grand Cherokee trim should I buy?

The 2020 Jeep Grand Cherokee is offered in 12 trim levels: Laredo, Limited X, Summit, SRT, Trackhawk, and eight additional variants.

Here's the short version:

• Laredo: This is the entry point, so it makes sense if you want the Grand Cherokee’s core style and capability without stretching for extras. It’s the trim to start with if you care most about getting into the model at the lowest price.
• Limited X: This is the best-value choice if you want a more polished feel, because it adds the 8.4-inch Uconnect system, navigation, Apple CarPlay, Android Auto, and a more upscale appearance. It also suits you if you want the Grand Cherokee’s broad capability without jumping into the pricier luxury end.
• Summit: Choose this if you want the more premium side of the Grand Cherokee lineup and are willing to pay for it. The review notes that interior quality becomes more frustrating as prices climb, so this trim makes the most sense if you specifically want the richer equipment mix.
• SRT: This is the performance-focused choice for buyers who want serious power and track-oriented character. It stands apart from the regular trims because the review explicitly calls out its high-performance nature.
• Trackhawk: This is the extreme performance pick, with the review describing it as the most outrageous and fun version in the lineup. It suits you only if outright performance matters more than practicality or efficiency.

ProTech I is standard on all trim levels, while Premium Lighting Group equipment is standard in higher trim levels.

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

This is a moderate, selective buyer’s market, so you can shop with some leverage if you’re patient.

• Deal availability: 33.8% of listings are priced as good or great deals.
• Inventory: There are 591 listings available.
• Price trend: Prices have softened 16.68% compared with last year.

If you find a listing below $25,176 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 $25,176 CAD sits slightly below last year's $30,216 CAD.

That softer pricing suggests the model has already absorbed a meaningful amount of depreciation, which can help future sellers if they buy at the right price. If you purchase near the current average or below, you may reduce the amount of value left to lose over the next ownership period.

The flip side is that a model with a weaker value-for-money reputation can be harder to position at resale unless it’s well equipped and well maintained. Strong demand from shoppers who want style and capability should still help support interest in the used market.

Vehicles with strong owner satisfaction ratings, like this model year's 4.6/5, tend to retain buyer demand, which supports resale value over time.

Is the 2020 Jeep Grand Cherokee safe?

The 2020 Jeep Grand Cherokee earns a Marginal rating for driver protection and a Poor rating for front passenger protection in the IIHS small overlap frontal-impact test, and it earns an overall four-star rating from NHTSA.

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

Jeep offers three ADAS packages for this model. ProTech I 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. 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 that advanced safety features are not standard, and the crash-test results are a real weakness for used shoppers who prioritise protection.

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:

• 33.8% of listings are priced as good or great deals.
• Price trend: Prices have softened 16.68% compared with last year.
• Owners rate it 4.6/5 — a strong satisfaction signal.
• It combines stylish design with strong off-road capability, but advanced safety features are not standard.

Consider the 2021 if:

• At $28,916 CAD, the 2021 costs more than the current year's $25,176 CAD average.
• It is the final version before the redesign arrives.

The bottom line: Choose the 2020 if you want the better price and are comfortable with its age and safety compromises. Consider the 2021 if you want the last version of the old formula and are willing to pay more for it.

How does the 2020 Jeep Grand Cherokee compare to the 2020 Ford Explorer?

Expert Pros & Cons (per CarGurus review team)

2020 Jeep Grand Cherokee:

• Pros: Stylish design, Off-road capability.
• Cons: Advanced safety features are not standard, Poor value for money.

2020 Ford Explorer:

• Pros: Stylish design, Spacious.
• Cons: Interior materials feel cheap, Poor value for money.

Our experts score the 2020 Jeep Grand Cherokee 6.3/10 and the 2020 Ford Explorer 7.2/10. The Grand Cherokee leans harder into off-road capability, while the Explorer is the more spacious choice. Both have value concerns, but the Explorer’s higher score suggests a stronger overall package despite its interior-material drawback.

Read our full side-by-side expert comparison here.

These recommendations are based on CarGurus' proprietary market data from November 10, 2026, CarGurus experts' opinions, and generative AI.