Used 2021 Jeep Grand Cherokee for Sale nearChicago, IL

Compare 2021 Jeep Grand Cherokee Trims in Chicago, IL

The 2021 Jeep Grand Cherokee offers a range of trims from budget-friendly options to luxury models, all featuring robust 4WD capabilities.

• Starting at $17,670
• 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 E 4WD — "Who It's For"

The Laredo E 4WD is the pick for shoppers who want a budget-friendly SUV without sacrificing essential features.

• Avg. market price: $17,670 (updated weekly)
• MPG/MPGe: 18 city / 25 hwy
• Inventory: 54 listings
• View Laredo E 4WD listings

Laredo X 4WD — "Who It's For"

The Laredo X 4WD is the pick for shoppers who want added features like a sunroof and navigation without a hefty price tag.

• Avg. market price: $22,026 (updated weekly)
• MPG/MPGe: 18 city / 25 hwy
• Inventory: 63 listings
• View Laredo X 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.

• Avg. market price: $23,991 (updated weekly)
• MPG/MPGe: 19 city / 26 hwy
• Inventory: 60 listings
• View Limited RWD listings

Limited 4WD — "Who It's For"

The Limited 4WD is the pick for shoppers who want a blend of luxury and capability, making it the most popular trim in the lineup.

• Avg. market price: $22,263 (updated weekly)
• MPG/MPGe: 18 city / 25 hwy
• Inventory: 347 listings — widest selection in the lineup
• View Limited 4WD listings

Overland 4WD — "Who It's For"

The Overland 4WD is the pick for shoppers who want a sporty SUV with luxury features and off-road capability.

• Avg. market price: $25,085 (updated weekly)
• MPG/MPGe: 18 city / 25 hwy
• Inventory: 269 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 off-road capability, making it ideal for serious adventurers.

• Avg. market price: $29,927 (updated weekly)
• MPG/MPGe: 18 city / 25 hwy
• Inventory: 171 listings — widest selection in the lineup
• View Summit 4WD listings

Trim Recommendations

Most Popular — Limited 4WD

With 347 active listings, the Limited 4WD is the clear volume leader in the lineup.

Browse Limited 4WD listings

Best Budget Option — Laredo E 4WD

At $17,670 avg market price — below the lineup median of $23,127 — 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 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 2021 Jeep Grand Cherokee cost?

Prices have softened 11.57% compared to this time last year, making it a favorable time to shop this model year.

There are 6,478 listings available, which suggests solid inventory for comparison shopping.

If you find a listing below $22,570.93, that's toward the low end of the year-round range and worth acting on quickly.

Is the 2021 Jeep Grand Cherokee a good car?

Yes — 4.62/5 from owners, paired with a 7.17/10 expert rating, points to a model that resonates with shoppers even as it shows its age. The standout strength is Look and feel at 9/10.

Owners consistently praise the spacious interior, smooth ride, impressive power, off-road capability, advanced technology features, and luxury feel. Those themes line up with the Grand Cherokee’s polished design and upscale cabin, which help it feel more premium than many midsize SUVs.

The trade-offs are clear: the base engine is underwhelming, and some owners wish for more tech features for the price. In practical terms, this is a good fit if you want a two-row SUV with a more upscale personality and broad capability rather than the newest design.

With 33.4% of listings marked as good or great deals, there is enough market flexibility to shop selectively.

Is the 2021 Jeep Grand Cherokee reliable?

Owners rate it 4.62/5, a strong signal of long-term satisfaction.

The owner feedback also points to a dependable-feeling ownership experience, with repeated praise for comfort, smoothness, and the kind of capability people can count on over time. That matters if you want a used SUV that feels settled and proven rather than experimental.

Jeep’s free scheduled maintenance for the first three years and 36,000 miles adds a helpful ownership perk for buyers who are still within that window.

For used buyers, the main long-term risk is less about basic satisfaction and more about buying a poorly maintained example with aging components or deferred upkeep.

What should I look for when buying a used 2021 Jeep Grand Cherokee?

At 74.3% 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 are considering a higher-mileage example or one with off-road use. Focus on body condition, panel fit, tire wear, and signs of uneven repair quality, since those can reveal more than a quick test drive.

Key things to evaluate:

• Trim level: The lineup spans affordable Laredo and Limited versions, upscale Overland and Summit models, plus Trailhawk for serious off-road use and SRT and Trackhawk for performance-focused buyers. Base trims are more likely to leave out the premium touches that make the Grand Cherokee feel special.
• Powertrain: The standard 3.6-liter V6 makes 295 horsepower and 260 pound-feet of torque, while the optional 5.7-liter V8 makes 360 hp and 390 lb-ft and adds stronger towing and more urgency.
• Safety package: The ProTech II Package bundles adaptive cruise control with full stop-and-go, forward-collision warning, automatic emergency braking, blind-spot monitoring, rear cross-traffic alert, lane-departure warning, lane-keeping assistance, and automatic high-beam headlights. Some trims do not include all of these features.
• Infotainment: The Uconnect 4C with Nav system includes navigation, Apple CarPlay, Android Auto, a 4G LTE WiFi hotspot, and Jeep Skill for Amazon Alexa.
• Fuel efficiency: The V8 is described as returning no more than 17 mpg in combined driving.

Which 2021 Jeep Grand Cherokee trim should I buy?

The 2021 Jeep Grand Cherokee is offered in 8 trim levels: Laredo, Limited, Laredo X, 80th Anniversary Edition, Overland, Summit, Trailhawk, SRT, and Trackhawk.

Here's the short version:

• Laredo: This is the entry point if you want the Grand Cherokee formula at the lowest price, but it is the trim most likely to feel stripped back compared with the richer versions above it.
• Limited: This is the best-value trim for most shoppers because it adds a more upscale feel without pushing you into the expensive luxury end of the lineup.
• Laredo X: Choose this if you want a value-oriented version with a little more equipment than the standard Laredo.
• 80th Anniversary Edition: This is for you if you want a commemorative version with a more distinctive presentation.
• Overland: This is the right step up if you want a more premium Grand Cherokee without going all the way to Summit.
• Summit: This is the luxury pick, with the richest cabin presentation and the most upscale feel in the lineup.
• Trailhawk: Choose this if off-road use matters most, since it is the dedicated adventure-oriented version.
• SRT: This is the performance-focused choice if you want the track-oriented model.
• Trackhawk: This is the most extreme performance model in the lineup.

The safety content also makes clear that advanced safety features vary by trim, so it is worth checking equipment carefully before you buy.

Is now a good time to buy a used 2021 Jeep Grand Cherokee?

This is a moderate market for selective buyers, with enough inventory and pricing softness to reward patience.

• Deal availability: 33.4% of listings are priced as good or great deals.
• Inventory: There are 6,478 listings available.
• Price trend: Prices have softened 11.57% compared with last year.
• Clean inventory: 74.3% of listings are accident-free.

If you find a listing below $22,570.93, that's toward the low end of the year-round range and worth acting on quickly.

What is the 2021 Jeep Grand Cherokee's resale value?

The current average of $22,566 sits slightly below last year's $25,518.

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. A softer market can also make it easier to find a well-equipped example without paying peak pricing.

If demand stays steady, the Grand Cherokee’s broad appeal and premium image should help support resale better than a less distinctive midsize SUV. Buying near the lower end of the range gives you more room to protect your value later.

Vehicles with strong owner satisfaction ratings, like this model year's 4.62/5, tend to retain buyer demand, which supports resale value over time.

Is the 2021 Jeep Grand Cherokee safe?

A 2021 Grand Cherokee with 4WD earns a five-star overall rating from NHTSA, while 2WD versions drop to four-star overall ratings because of a three-star rollover resistance rating.

It earns a 4/10 safety score from our experts.

The safety picture is mixed because the Grand Cherokee’s active safety equipment is strong when equipped, but its crash-test performance is a real drawback. The IIHS results are especially concerning: the SUV earns a Marginal rating for the driver and a Poor rating for the front passenger in small-overlap frontal testing, and its headlights also rate Poor unless you upgrade to the high-intensity discharge setup with automatic high-beam assist.

Jeep’s ProTech II Package adds adaptive cruise control with full stop-and-go, forward-collision warning, automatic emergency braking, blind-spot monitoring, rear cross-traffic alert, lane-departure warning, lane-keeping assistance, and automatic high-beam headlights. That package helps, but it is not standard across the lineup, so you should verify exactly what a used example includes.

Should I buy a 2021 Jeep Grand Cherokee or consider a different year?

If you're weighing the 2021 against nearby model years, here's how to think about it:

Choose the 2021 if:

• 33.4% of listings are priced as good or great deals.
• At 74.3% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.
• Price trend: Prices have softened 11.57% compared with last year.
• Owners rate it 4.62/5 — a strong satisfaction signal.
• This is the last version of the two-row Grand Cherokee before the redesign arrives.

Consider the 2020 if:

• At $20,478, the 2020 costs less than the current year's $22,566 average.
• It is a long-running version with broad capability and familiar appeal.

Consider the 2022 if:

• At $27,369, the 2022 costs more than the current year's $22,566 average.
• It brings a redesigned cabin with a noticeable step up in technology and sophistication.

The bottom line: If you want the familiar two-row Grand Cherokee formula and a softer used price, the 2021 is the smart middle ground. If your priority is saving money, the 2020 is the better value play. If you want the newer design and can stretch your budget, the 2022 is the more modern choice.

These recommendations are based on CarGurus' proprietary market data from September 4, 2026, CarGurus experts' opinions, and generative AI.