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 $15,380
• 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 breaking the bank. It's a great entry point into the Grand Cherokee lineup.

• Avg. market price: $15,995 (updated weekly)
• MPG/MPGe: 18 city / 25 hwy
• Inventory: 211 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 added features like navigation without paying for higher trims. It's an affordable AWD option.

• Avg. market price: $15,380 (updated weekly)
• MPG/MPGe: 18 city / 25 hwy
• Inventory: 61 listings
• View Laredo E 4WD listings

Limited RWD — "Who It's For"

The Limited RWD is the pick for shoppers who want a standard trim with a good balance of features and price. It offers a solid value for those who don't need AWD.

• Avg. market price: $22,310 (updated weekly)
• MPG/MPGe: 19 city / 26 hwy
• Inventory: 54 listings
• View Limited RWD listings

Altitude 4WD — "Who It's For"

The Altitude 4WD is the pick for shoppers who want a sporty look and AWD capability without going for the higher trims. It combines style with functionality.

• Avg. market price: $23,094 (updated weekly)
• MPG/MPGe: 18 city / 25 hwy
• Inventory: 261 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 at a reasonable price. It's the most popular trim for good reason.

• Avg. market price: $17,364 (updated weekly)
• MPG/MPGe: 18 city / 25 hwy
• Inventory: 820 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 combined with luxury features. It's designed for adventure seekers.

• Avg. market price: $20,645 (updated weekly)
• MPG/MPGe: 18 city / 25 hwy
• Inventory: 54 listings
• View Trailhawk 4WD listings

Overland 4WD — "Who It's For"

The Overland 4WD is the pick for shoppers who want a premium SUV experience with advanced features. It balances luxury and performance well.

• Avg. market price: $24,425 (updated weekly)
• MPG/MPGe: 18 city / 25 hwy
• Inventory: 186 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 the ultimate luxury and capability in an SUV. It's designed for those who demand the best.

• Avg. market price: $27,386 (updated weekly)
• MPG/MPGe: 18 city / 25 hwy
• Inventory: 110 listings — widest selection in the lineup
• View Summit 4WD listings

Trim Recommendations

Most Popular — Limited 4WD

With 820 active listings, the Limited 4WD is the clear volume leader in the lineup.

Browse Limited 4WD listings

Best Budget Option — Laredo E 4WD

At $15,380 avg market price — below the lineup median of $21,477 — it's the most accessible entry point.

Browse Laredo E 4WD listings

Best for Fuel Economy — Limited RWD

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

Browse Limited RWD listings

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

How much does the 2020 Jeep Grand Cherokee cost?

Prices have softened 10.29% compared to this time last year, making it a favorable time to shop this model year.

There are 6,935 listings available, which suggests you should have a healthy set of options 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 ride quality. The SUV’s stylish design and off-road capability help it stand out, and it fits buyers who want a versatile midsize SUV with a strong personality. The trade-offs are that advanced safety features are not standard and value for money is weak. With 34.5% of listings marked as good or great deals, the market still 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.

Owner feedback points to a dependable-feeling SUV with comfort and performance that many drivers feel confident living with over time. The expert review also describes it as an appealing choice that remains popular despite its age, and it notes that the Grand Cherokee’s broad talent set is part of its staying power. Jeep’s standard 8-speed automatic and the model’s traditional SUV character reinforce that sense of durability and familiarity. For used buyers, the main long-term risk is that age-related wear and uneven build quality can matter more than the badge or capability.

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

At 68.6% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.

You should run a vehicle history report before you commit, then prioritize a pre-purchase inspection that focuses on bodywork, suspension behavior, and signs of prior repair. Because this SUV is now well into its production run, condition matters more than mileage alone, especially if you want the version that best matches how you plan to use it.

Key things to evaluate:

• Trim level: The Grand Cherokee’s lineup spans from the Laredo to the Summit, with additional variants in between, plus higher-priced SRT and Trackhawk versions. Base versions can feel less richly equipped than pricier trims, and the Premium Lighting Group is important because the headlights rate poorly without it.
• Powertrain: The standard setup is a 295-horsepower, 3.6-liter V6 with an 8-speed automatic. If you want more power, V8 options are available, and the Trailhawk is the version aimed at serious off-road use.
• 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 plan is available, and some versions offer a 19-speaker Harman Kardon audio system.
• Fuel efficiency: The standard V6 returned 21 mpg in combined driving in the expert test vehicle, and the test vehicle achieved 19.4 mpg in real-world driving.

Which 2020 Jeep Grand Cherokee trim should I buy?

The 2020 Jeep Grand Cherokee is offered in 11 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’s core style and capability at the lowest starting price. It is the trim to skip if you want the richer equipment and lighting upgrades that help the higher versions feel more complete.
• Limited X: This is the best-value trim for many shoppers because it adds the 8.4-inch touchscreen, navigation, Apple CarPlay, Android Auto, Amazon Alexa, SiriusXM, and connected services. It also pairs well with the Grand Cherokee’s strong styling and gives you a more polished daily-driving experience without jumping to the most expensive versions.
• Trailhawk: Choose this if off-road use matters most, since it is the version built to travel well off the beaten path with all-terrain tires, skid plates, and the most capable 4WD system. It suits you if trail ability matters more than luxury touches.
• SRT: This is the performance-focused choice, with the kind of power and track-ready character that makes sense only if you want the Grand Cherokee’s most aggressive road manners. It is not the value pick, but it is the right fit if performance is your priority.
• Trackhawk: This is the extreme performance trim, aimed at buyers who want the most outrageous power and the most specialized hardware in the lineup. It is for you only if you want the top-end performance story and are comfortable paying for it.

The safety package starts with ProTech I on all trims, while ProTech II and Advanced ProTech II add more advanced driver-assistance features as you move up.

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 carefully and still find worthwhile listings.

• Deal availability: 34.5% of listings are priced as good or great deals.
• Inventory: There are 6,935 listings available.
• Price trend: Prices have softened 10.29% compared with last year.
• Clean inventory: 68.6% of listings are accident-free.

If you find a listing below $19,919, 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 $19,920 sits slightly below last year's $22,205.

That price movement suggests the model has already absorbed a meaningful amount of depreciation, which can help future sellers if they buy at the right price today. If you purchase near the lower end of the current range, you may have a better chance of limiting further loss when it is time to sell. The Grand Cherokee’s broad appeal and strong owner satisfaction can help support demand, but its age and value concerns still matter.

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 four-star overall rating from NHTSA. In IIHS testing, it earns a Marginal rating for driver protection and a Poor rating for 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 systems. 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 headlight rating is poor unless you upgrade.

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:

• 34.5% of listings are priced as good or great deals.
• At 68.6% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.
• Price trend: Prices have softened 10.29% compared with last year.
• Owners rate it 4.6/5 — a strong satisfaction signal.
• The 2020 stands out for its stylish design, off-road capability, and broad range of trims and powertrains.

Consider the 2019 if:

• At $17,839, the 2019 costs less than the current year's $19,920 average.
• It offers strong everyday usability with broad appeal and a balanced on-road/off-road character.

Consider the 2021 if:

• At $21,903, the 2021 costs more than the current year's $19,920 average.
• It adds a more upscale feel with premium interior materials and great handling.

The bottom line: If you want the best mix of price, selection, and the Grand Cherokee’s classic character, the 2020 is the primary year to target. If your budget is tighter, the 2019 is the better value play; if you want a newer-feeling cabin and can spend more, the 2021 is worth a look.

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 is the better pick if you care more about off-road ability and a traditional SUV feel. The Explorer looks like the stronger all-around choice here because it scores higher and offers more space, though its interior materials are a drawback. Both are criticized for value, so your decision comes down to whether you want capability or cabin room.

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

These recommendations are based on CarGurus' proprietary market data from October 27, 2026, CarGurus experts' opinions, and generative AI.