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 10.11% compared to this time last year, making it a favorable time to shop this model year.

There are 7,007 listings available, which suggests you have a healthy amount of inventory to compare.

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 many also like the powerful engines, especially the V8, plus the ride quality. The trade-offs are familiar: some drivers want better gas mileage, and others mention seating comfort issues for taller people and some build-quality concerns.

Given its broad appeal as a versatile five-passenger midsize SUV, it makes sense if you want something that can feel at home in very different settings. Even so, the market still reflects its mixed value proposition, so the 34.0% good-or-great-deal share is worth watching closely.

Is the 2020 Jeep Grand Cherokee reliable?

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

The owner feedback also points to a dependable, trouble-free ownership experience for many shoppers, with comfort and performance standing out as recurring strengths. The expert test-drive notes reinforce that sense of durability by describing it as a traditional SUV that remains capable in demanding use, including off-road driving.

Jeep also includes a maintenance perk in the ownership experience for some buyers, which can help early running costs. For used shoppers, the main long-term risk is that age-related wear and uneven upkeep can matter more than the badge itself, so condition and service history should carry real weight.

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

At 68.8% 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 thorough pre-purchase inspection, especially if you’re considering a higher-mileage example or one with off-road use. Focus on body condition, suspension behavior, tire wear, and signs that the vehicle has been maintained consistently.

Key things to evaluate:

• Trim level: The base Laredo starts the lineup, while higher trims add more premium materials and equipment; the Premium Lighting Group is standard in higher trim levels, which matters because the headlights are rated poorly without it.
• Powertrain: The standard setup is a 295-horsepower, 3.6-liter V6 with an 8-speed automatic, and V8 options are available if you want more power and torque.
• 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: 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 data plan is available, and some versions offer a 19-speaker Harman Kardon audio system.
• Fuel efficiency: The test vehicle returned 21 mpg in combined driving according to the EPA, and the test vehicle itself achieved 19.4 mpg.

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 Trailhawk.

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 extras. It’s the trim to start with if you care more about the SUV’s personality than luxury add-ons.
• Trailhawk: This is the best fit if off-road ability is your priority, since it comes with all-terrain tires, skid plates, and Jeep’s most capable 4WD system. Choose it if you want the Grand Cherokee’s rugged side front and center.
• Limited X: This is the best-value pick for many shoppers because it adds a strong mix of comfort and tech, including the 8.4-inch touchscreen, navigation, Apple CarPlay, Android Auto, Amazon Alexa, and SiriusXM Guardian. It also shows how the Grand Cherokee can feel more upscale without jumping all the way to the expensive trims.
• Summit: This is the trim to consider if you want a more premium feel and are willing to pay for it. It sits near the top of the range and is aimed at buyers who want the Grand Cherokee’s style with more luxury content.
• SRT: This is the performance-focused choice, with a 6.4-liter Hemi V8 and performance-oriented hardware. It suits you if you want the Grand Cherokee to feel much more aggressive on pavement.
• Trackhawk: This is the extreme performance model, with a supercharged 6.2-liter V8 and track-ready capability. It’s for buyers who want the most powerful and most outrageous version of the lineup.

The safety package is a real consideration here: ProTech I is standard, but the more advanced driver-assistance features are reserved for higher equipment levels.

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 with some leverage if you’re patient.

• Deal availability: 34.0% of listings are priced as good or great deals.
• Inventory: There are 7,007 listings available.
• Price trend: Prices have softened 10.11% compared with last year.
• Clean inventory: 68.8% of listings are accident-free.

If you find a listing below $20,474, 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 $20,476 sits slightly below last year's $22,779.

That decline suggests the market has already adjusted downward, which can help you buy more confidently now but may also limit near-term upside if you plan to sell soon. For a future seller, the key is to buy well and keep the vehicle in strong condition, because a softer market can make overpaying harder to recover later.

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

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

Jeep offers three collections of driver-assistance features. 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.

A key caveat is that advanced safety features are not standard, and the headlights rate Poor unless you upgrade to 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:

• 34.0% of listings are priced as good or great deals.
• At 68.8% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.
• Price trend: Prices have softened 10.11% compared with last year.
• Owners rate it 4.58/5 — a strong satisfaction signal.
• It blends strong off-road capability with stylish design and broad everyday appeal.

Consider the 2019 if:

• At $18,215, the 2019 costs less than the current year's $20,476 average.
• It offers rare on-road and off-road versatility with easy daily drivability.

Consider the 2021 if:

• At $22,505, the 2021 costs more than the current year's $20,476 average.
• It brings a more upscale feel with premium materials and strong handling.

The bottom line: If you want the best balance of price, availability, and the Grand Cherokee’s signature capability, the 2020 is the sensible default. If you’re especially price-sensitive, the 2019 is the better value play; if you want a newer-feeling cabin and can spend more, the 2021 is the upgrade path to consider.

These recommendations are based on CarGurus' proprietary market data from September 11, 2026, CarGurus experts' opinions, and generative AI.