Used 2020 Jeep Grand Cherokee for Sale nearMilwaukee, WI

Compare 2020 Jeep Grand Cherokee Trims in Milwaukee, WI

The 2020 Jeep Grand Cherokee offers a range of trims from budget-friendly options to well-equipped models, all featuring robust 4WD capabilities.

• Starting at $18,388
• Best MPG/MPGe: 19 city / 26 hwy
• Most Popular: Limited 4WD

Trim Overview

Prices updated weekly from CarGurus listings.

Quick Compare Table

Listing prices sourced from CarGurus — updated weekly. OEM specs from manufacturer data.

Missing data displayed as "—".

Trim Deep Dives

Laredo 4WD — "Who It's For"

The Laredo 4WD is the pick for shoppers who want a well-equipped SUV without paying for luxury features.

• Avg. market price: $18,388 (updated weekly)
• MPG/MPGe: 18 city / 25 hwy
• Inventory: 206 listings — widest selection in the lineup
• View Laredo 4WD listings

Laredo E 4WD — "Who It's For"

The Laredo E 4WD is the pick for shoppers who want sporty features and all-wheel drive without stepping up to higher trims.

• Avg. market price: $24,663 (updated weekly)
• MPG/MPGe: 18 city / 25 hwy
• Inventory: 54 listings
• View Laredo E 4WD listings

Limited RWD — "Who It's For"

The Limited RWD is the pick for shoppers who want a balance of luxury and performance without the 4WD price tag.

• Avg. market price: $24,663 (updated weekly)
• MPG/MPGe: 19 city / 26 hwy
• Inventory: 53 listings
• View Limited RWD listings

Altitude 4WD — "Who It's For"

The Altitude 4WD is the pick for shoppers who want stylish features and AWD capability at a lower price.

• Avg. market price: $21,789 (updated weekly)
• MPG/MPGe: 18 city / 25 hwy
• Inventory: 315 listings — widest selection in the lineup
• View Altitude 4WD listings

Limited 4WD — "Who It's For"

The Limited 4WD is the pick for shoppers who want a well-rounded SUV with premium features and 4WD capability.

• Avg. market price: $19,946 (updated weekly)
• MPG/MPGe: 18 city / 25 hwy
• Inventory: 880 listings — widest selection in the lineup
• View Limited 4WD listings

Trailhawk 4WD — "Who It's For"

The Trailhawk 4WD is the pick for shoppers who want off-road capability without breaking the bank.

• Avg. market price: $18,999 (updated weekly)
• MPG/MPGe: 18 city / 25 hwy
• Inventory: 61 listings
• View Trailhawk 4WD listings

Overland 4WD — "Who It's For"

The Overland 4WD is the pick for shoppers who want premium features and a sporty ride in an SUV.

• Avg. market price: $24,663 (updated weekly)
• MPG/MPGe: 18 city / 25 hwy
• Inventory: 204 listings — widest selection in the lineup
• View Overland 4WD listings

Summit 4WD — "Who It's For"

The Summit 4WD is the pick for shoppers who want luxury features and serious off-road capability.

• Avg. market price: $24,267 (updated weekly)
• MPG/MPGe: 18 city / 25 hwy
• Inventory: 125 listings — widest selection in the lineup
• View Summit 4WD listings

Trim Recommendations

Most Popular — Limited 4WD

With 880 active listings, the Limited 4WD is the clear volume leader in the lineup.

Browse Limited 4WD listings

Best Budget Option — Laredo 4WD

At $18,388 avg market price — below the lineup median of $23,028 — it's the most accessible entry point.

Browse Laredo 4WD listings

Best for Fuel Economy — Limited RWD

The Limited RWD offers the best fuel economy in the lineup with 19/26 MPG.

Browse Limited RWD listings

These recommendations are based on CarGurus' proprietary market data from September 2, 2026, CarGurus experts' opinions, and generative AI.

How much does the 2020 Jeep Grand Cherokee cost?

Prices have softened 9.80% compared to this time last year, making it a favorable time to shop this model year.

There are 6,982 listings available, which suggests solid inventory for comparison shopping.

If you find a listing below $20,639.98, that's toward the low end of the year-round range and worth acting on quickly.

Is the 2020 Jeep Grand Cherokee a good car?

Yes — the 2020 Jeep Grand Cherokee 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 highlight the powerful engines and ride quality. The review summary also points to its advanced safety options and strong overall appeal for buyers who want a capable, upscale SUV.

The trade-offs are clear: the base setup is not especially value-focused, and the source calls out poor value for money along with some concerns about gas mileage and seating comfort for taller passengers. It also fits best if you want a midsize SUV that can handle both daily driving and off-road use.

With 29.1% of listings marked as good or great deals, there is enough market softness to make selective shopping worthwhile.

Is the 2020 Jeep Grand Cherokee reliable?

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

The owner summary points to a dependable-feeling SUV with strong comfort, performance, and luxury appeal, and it also notes that many drivers appreciate the powerful engines and ride quality over time. The expert drive notes reinforce that it behaves like a traditional SUV and can handle serious off-road use, which supports the sense that it is built for long-term versatility.

The cost-effectiveness discussion also suggests that its value is tied to capability rather than low running costs, so you should expect ownership to make the most sense if you actually use its strengths. For used buyers, the main long-term risk is that a neglected example may carry more wear-related issues than a simpler crossover.

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

At 69.4% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.

You should start with a vehicle history report and then prioritize a pre-purchase inspection, especially if the listing price looks unusually attractive. Focus on body condition, signs of prior repair, and whether the vehicle’s equipment and trim match the seller’s description.

Key things to evaluate:

• Trim level: The lineup starts with the Laredo and rises through Summit, with additional variants in between; the source also notes that higher-priced versions can feel let down by hard plastic in the cabin. The Limited X example adds a more upscale appearance with a ventilated hood, sport-themed front bumper, and 20-inch wheels.
• Powertrain: The standard setup is a 295-horsepower, 3.6-liter V6 with an 8-speed automatic, and the lineup also includes three V8 options for buyers who want more power. The Trailhawk is the off-road-focused choice, while the SRT and Trackhawk are the high-performance versions.
• 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, 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.
• Infotainment: Limited X trim includes an 8.4-inch touchscreen, navigation, Apple CarPlay, Android Auto, Amazon Alexa, SiriusXM satellite radio, and SiriusXM Guardian connected services. A 4G LTE WiFi plan is available, and some versions can be equipped with a 19-speaker Harman Kardon audio system.
• Fuel efficiency: The standard V6 returns 21 mpg in combined driving according to the EPA, and the test vehicle returned 19.4 mpg in real-world driving.

Which 2020 Jeep Grand Cherokee trim should I buy?

The 2020 Jeep Grand Cherokee is offered in 10 trim levels: Laredo, Summit, Limited X, SRT, Trackhawk, Trailhawk, and the additional variants mentioned between the bookends.

Here's the short version:

• Laredo: This is the entry point, so it makes sense if you want the Grand Cherokee formula at the lowest starting price. It gives you the core styling and capability, but the source makes clear that advanced safety features are not standard, so you may want to move up if those matter to you.
• Limited X: This is the best-value choice if you want a more upscale feel without jumping into the most expensive territory. It adds the 8.4-inch touchscreen, navigation, smartphone integration, and a more distinctive appearance, making it a strong middle-ground pick.
• Summit: Choose this if you want the most premium mainstream Grand Cherokee experience and are willing to pay for it. The source suggests that higher-priced versions can be undermined by hard plastics, so this trim is best if you care more about equipment and image than pure value.
• Trailhawk: Pick this if off-road use is a real priority. It is the version built for the trail, with all-terrain tires, skid plates, and the most capable 4WD system described in the source.
• SRT: This is the performance-focused choice for buyers who want serious power and sharper on-road pace. It is the right fit if you care more about acceleration and driving excitement than efficiency.
• Trackhawk: This is the extreme performance trim, with the most powerful engine mentioned and track-ready hardware. It is the one to buy only if you want maximum output and are comfortable with the trade-offs that come with it.

ProTech I is standard, while ProTech II and Advanced ProTech II add more driver-assistance features as you move up the range.

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

The market looks moderate and selective buyers should have room to shop carefully.

• Deal availability: 29.1% of listings are priced as good or great deals.
• Inventory: There are 6,982 listings available.
• Price trend: Prices have softened 9.80% compared with last year.
• Clean inventory: 69.4% of listings are accident-free.

If you find a listing below $20,639.98, 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 $20,632 sits slightly below last year's $22,874.

That price movement suggests the model has already absorbed some depreciation, which can help future sellers if they buy at the right price today. If you purchase near the lower end of the range and keep the vehicle in strong condition, you may have a better chance of limiting your loss later. The strongest resale prospects will likely come from well-kept examples with desirable equipment and clean history.

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?

It earns four-star ratings overall from NHTSA and a 3/10 safety score from our experts.

Jeep’s ProTech I suite 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, 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 that the Grand Cherokee’s crash-test performance is weak for its class, including a Marginal driver-protection result, a Poor front-passenger result in the small overlap frontal test, and Poor headlights unless you move to the better lighting package. That makes trim and option selection especially important if safety is a top priority.

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:

• 29.1% of listings are priced as good or great deals.
• At 69.4% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.
• Price trend: Prices have softened 9.80% compared with last year.
• Owners rate it 4.58/5 — a strong satisfaction signal.
• It balances daily driving with serious off-road capability while still offering strong engine choices.

Consider the 2019 if:

• At $18,308, the 2019 costs less than the current year's $20,632 average.
• It offers broad appeal for buyers who want one SUV for both pavement and rougher terrain.

Consider the 2021 if:

• At $22,712, the 2021 costs more than the current year's $20,632 average.
• It is the final version before the redesign and keeps the familiar two-row Grand Cherokee formula.

The bottom line: If you want the best balance of price, availability, and the classic Grand Cherokee mix of comfort and capability, the 2020 is the primary path to consider. If your budget is tighter, the 2019 is the smarter price-sensitive alternative, while the 2021 makes sense if you want the last year of this generation and are willing to pay more.

These recommendations are based on CarGurus' proprietary market data from August 28, 2026, CarGurus experts' opinions, and generative AI.