Used 2020 Jeep Grand Cherokee for Sale nearChicago, IL

Compare 2020 Jeep Grand Cherokee Trims in Chicago, IL

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 $17,245
• 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 offers a solid mix of features and capability.

• Avg. market price: $19,934 (updated weekly)
• MPG/MPGe: 18 city / 25 hwy
• Inventory: 277 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 enhanced features and all-wheel drive without a hefty price tag.

• Avg. market price: $17,318 (updated weekly)
• MPG/MPGe: 18 city / 25 hwy
• Inventory: 72 listings
• View Laredo E 4WD listings

Limited RWD — "Who It's For"

The Limited RWD is the pick for shoppers who want a well-rounded SUV with a focus on comfort and technology without going overboard on price.

• Avg. market price: $21,187 (updated weekly)
• MPG/MPGe: 19 city / 26 hwy
• Inventory: 63 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 all-wheel drive capability without the highest price tag.

• Avg. market price: $20,117 (updated weekly)
• MPG/MPGe: 18 city / 25 hwy
• Inventory: 335 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 balance of luxury and capability without stepping up to the higher trims.

• Avg. market price: $18,779 (updated weekly)
• MPG/MPGe: 18 city / 25 hwy
• Inventory: 382 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 and premium features without the highest price tag.

• Avg. market price: $17,245 (updated weekly)
• MPG/MPGe: 18 city / 25 hwy
• Inventory: 62 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 and luxury touches.

• Avg. market price: $23,343 (updated weekly)
• MPG/MPGe: 18 city / 25 hwy
• Inventory: 264 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 in luxury and technology in a capable SUV.

• Avg. market price: $25,175 (updated weekly)
• MPG/MPGe: 18 city / 25 hwy
• Inventory: 164 listings — widest selection in the lineup
• View Summit 4WD listings

Trim Recommendations

Most Popular — Limited 4WD

With 382 active listings, the Limited 4WD is the clear volume leader in the lineup.

Browse Limited 4WD listings

Best Budget Option — Trailhawk 4WD

At $17,245 avg market price — below the lineup median of $20,025 — it's the most accessible entry point.

Browse Trailhawk 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 October 15, 2026, CarGurus experts' opinions, and generative AI.

How much does the 2020 Jeep Grand Cherokee cost?

Prices have softened 10.17% compared to this time last year, making it a favorable time to shop this model year.

There are 6,980 listings available, which suggests solid inventory for shoppers comparing trims and condition.

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 call out the powerful engines, especially the V8, along with the ride quality and advanced safety options. The trade-offs are familiar: some drivers want better gas mileage, and others mention seating comfort for taller people and some build-quality concerns.

That mix fits the Grand Cherokee’s role as a versatile midsize SUV with strong style and off-road capability, but it also reflects the fact that it is not a fresh redesign and is still carrying some aging-vehicle compromises. Even so, 34.8% of listings are priced as good or great deals, which gives you room to shop selectively.

Is the 2020 Jeep Grand Cherokee reliable?

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

Owner feedback points to a vehicle that many people trust for comfort, performance, and a generally satisfying ownership experience, with repeated praise for its powerful engines and ride quality. The expert evaluation also describes it as an appealing choice with broad capability and strong personality, which supports the idea that it can be a dependable fit if you choose the right version for your needs.

The ownership picture is still shaped by age, so you should expect more variation from one used example to the next than you would with a newer SUV. A careful inspection and service-history review matter because long-term risk is more about condition and maintenance than the model’s basic appeal.

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

At 68.7% 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 has any accident history or incomplete service records. Focus on body condition, interior wear, and signs that the vehicle has been used hard, since the Grand Cherokee’s appeal often depends on how well it has been maintained. If you want the best ownership experience, compare equipment carefully so you do not end up with a trim that misses the features you expected.

Key things to evaluate:

• Trim level: The Grand Cherokee’s design still looks right, but the interior can feel less substantial as prices climb, with more hard plastic becoming noticeable in pricier versions. The Premium Lighting Group is standard in higher trim levels, which matters because the headlights rate poorly without the upgrade.
• Powertrain: The standard setup is a 295-horsepower, 3.6-liter V6 with an 8-speed automatic, and it returns 21 mpg in combined driving. If you want more power, V8 options are available, including a 5.7-liter Hemi V8 with 360 hp, a 6.4-liter Hemi V8 in the SRT, and a supercharged 6.2-liter V8 in the 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: In Limited X trim, Uconnect 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 test vehicle returned 21 mpg in combined driving, and the EPA rating is also 21 mpg combined. The Trackhawk is described as extremely powerful, but the content does not provide a fuel-economy figure for it.

Which 2020 Jeep Grand Cherokee trim should I buy?

The 2020 Jeep Grand Cherokee is offered in 1 trim level: Grand Cherokee.

Here's the short version:

The Grand Cherokee is best approached as a trim-by-trim equipment and powertrain decision rather than a simple base-versus-upgrade choice. The content highlights a wide spread of versions, from the standard model to high-performance variants, but the safest recommendation for most used buyers is to focus on the version that gives you the safety and infotainment features you actually want without overpaying for extras you may not use.

The safety package note is important here: ProTech I is standard, while ProTech II and Advanced ProTech II add more capability, so you should verify which driver-assistance bundle a specific listing has before you buy.

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

This is a moderate market for selective buyers, so you can shop with some leverage if you compare listings carefully.

• Deal availability: 34.8% of listings are priced as good or great deals.
• Inventory: There are 6,980 listings available.
• Price trend: Prices have softened 10.17% compared with last year.
• Clean inventory: 68.7% of listings are accident-free.

If you find a listing below $20,125, 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 $20,125 sits slightly below last year's $22,403.

That decline suggests the market has moved in buyers’ favor, which can make the Grand Cherokee easier to purchase now but may also mean future resale gains are more limited if depreciation continues at the same pace. For a seller, the key takeaway is that condition, equipment, and accident history will matter a lot when you try to stand out against a large pool of listings.

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, with a three-star rollover resistance rating for rear-wheel-drive versions. 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 driver-assistance bundles here. 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.

The main caution is that advanced safety features are not standard, and the crash-test results are a real weakness relative to the vehicle’s otherwise broad appeal.

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:

• 34.8% of listings are priced as good or great deals.
• At 68.7% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.
• Price trend: Prices have softened 10.17% compared with last year.
• Owners rate it 4.58/5 — a strong satisfaction signal.
• The 2020 remains an appealing, if flawed, choice with strong style and off-road capability.

Consider the 2019 if:

• At $17,970, the 2019 costs less than the current year's $20,125 average.
• It is a rare SUV that feels at home both on the road and off it.

Consider the 2021 if:

• At $22,137, the 2021 costs more than the current year's $20,125 average.
• It offers stylish design, premium interior materials, and great handling.

The bottom line: If you want the strongest balance of price and availability, the 2020 is the primary path to consider. If you are especially price-sensitive, the 2019 can save you money while keeping the same basic Grand Cherokee formula. If you want to spend more for a newer-feeling alternative, the 2021 is the better comparison point.

These recommendations are based on CarGurus' proprietary market data from October 13, 2026, CarGurus experts' opinions, and generative AI.