Used 2021 Jeep Grand Cherokee for Sale nearMilwaukee, WI

Compare 2021 Jeep Grand Cherokee Trims in Milwaukee, WI

The Grand Cherokee offers a range of trims from budget-friendly options to luxury models, all with robust V6 performance and versatile drivetrains.

• Starting at $20,716
• 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: $20,716 (updated weekly)
• MPG/MPGe: 18 city / 25 hwy
• Inventory: 52 listings
• View Laredo E 4WD listings

Laredo X 4WD — "Who It's For"

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

• Avg. market price: $25,693 (updated weekly)
• MPG/MPGe: 18 city / 25 hwy
• Inventory: 54 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 luxury touches without the 4WD price tag.

• Avg. market price: $24,813 (updated weekly)
• MPG/MPGe: 19 city / 26 hwy
• Inventory: 55 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 at a competitive price. It's also the most popular trim in the lineup.

• Avg. market price: $22,014 (updated weekly)
• MPG/MPGe: 18 city / 25 hwy
• Inventory: 881 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 luxury features and off-road capability without going for the highest trim.

• Avg. market price: $24,490 (updated weekly)
• MPG/MPGe: 18 city / 25 hwy
• Inventory: 203 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 experience in an SUV with off-road capability.

• Avg. market price: $30,527 (updated weekly)
• MPG/MPGe: 18 city / 25 hwy
• Inventory: 127 listings — widest selection in the lineup
• View Summit 4WD listings

Trim Recommendations

Most Popular — Limited 4WD

With 881 active listings, the Limited 4WD is the clear volume leader in the lineup.

Browse Limited 4WD listings

Best Budget Option — Laredo E 4WD

At $20,716 avg market price — below the lineup median of $24,651 — 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 September 12, 2026, CarGurus experts' opinions, and generative AI.

How much does the 2021 Jeep Grand Cherokee cost?

Prices have softened 11.55% compared to this time last year, making it a favorable time to shop this model year.

There are 6,523 listings available, which suggests solid inventory for comparison shopping.

Is the 2021 Jeep Grand Cherokee a good car?

Yes — with a 4.62/5 user rating and a 7.17/10 expert rating, it lands as a well-liked used SUV with broad appeal. The standout strength is Look and feel at 9/10.

Owners repeatedly praise the spacious interior, smooth ride, impressive power, off-road capability, advanced technology features, and luxury feel. The main trade-offs are that some shoppers felt it was missing a few premium features for the price, and gas mileage can be a weak point.

That lines up with the overview: you get a familiar two-row SUV with upscale styling, premium materials, and strong handling, but also a model that is nearing the end of its generation. With 35.6% of listings priced as good or great deals, the market still gives you room to shop carefully.

Is the 2021 Jeep Grand Cherokee reliable?

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

Owner feedback points to a vehicle people feel good about living with over time, especially because it is described as spacious, smooth, and capable enough to inspire confidence. The review summary also emphasizes that many drivers see it as a good value and appreciate its dependable-feeling mix of comfort, power, and utility.

The expert evaluation reinforces that sense of durability and everyday usability, noting that the Grand Cherokee is speedy, responsive, and fairly quiet inside. Jeep’s customer care program also includes free scheduled maintenance for the first three years and 36,000 miles of ownership.

For used buyers, the main long-term ownership risk is that age-related wear and maintenance history matter more here than on a newer redesign.

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

At 73.9% 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 inspection of bodywork, alignment, and any signs of prior repair. Because this model can be equipped very differently by trim, it also makes sense to focus on whether the specific example has the comfort, tech, and safety equipment you want.

Key things to evaluate:

• Trim level: The lineup spans the affordable Laredo and Limited, the upscale Overland and Summit, the Trailhawk for serious off-roading, and the SRT and Trackhawk for track-focused performance. Base trims are more likely to leave you without the richer materials and premium feel that make higher trims stand out.
• 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 effortless acceleration.
• Safety package: The ProTech II Package includes 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. Advanced safety features are not standard, so trim and package content matter.
• Infotainment: Uconnect 4C with Nav includes navigation, Apple CarPlay, Android Auto, a 4G LTE WiFi hotspot, and Jeep Skill for Amazon Alexa. The system also supports SiriusXM services and remote features through SiriusXM Guardian.
• Fuel efficiency: The V8 is described as returning no more than 17 mpg in combined driving, and the expert review notes that it can be thirsty in city use.

Which 2021 Jeep Grand Cherokee trim should I buy?

The 2021 Jeep Grand Cherokee is offered in 7 trim levels: Laredo, Limited, Laredo X, 80th Anniversary Edition, Overland, Summit, Trailhawk.

Here's the short version:

• Laredo: This is the entry point if you want the Grand Cherokee’s styling, V6 power, and core SUV capability at the lowest price. It makes sense if you care more about the nameplate’s fundamentals than luxury extras.
• Limited: This is the best-value trim for most shoppers because it adds a more upscale feel without pushing you into the expensive upper end of the range. It’s the trim to target if you want a balanced mix of comfort, equipment, and price.
• Laredo X: This is a value-oriented step up that adds a little more appeal than the standard Laredo while staying on the affordable side of the lineup.
• 80th Anniversary Edition: This is the commemorative choice if you want a special-edition version with extra visual distinction.
• Overland: This is the better pick if you want a more premium cabin and a more upscale ownership experience.
• Summit: This is the luxury-leaning choice, with the richest interior presentation and the most polished feel in the lineup.
• Trailhawk: This is the one to buy if your priorities include serious off-road use and you want the most trail-ready setup.

Safety-package note: advanced safety features are not standard, so check carefully for the ProTech II Package or equivalent equipment on any trim you consider.

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

This is a moderate, selective buyer’s market, so you can shop with some leverage if you’re patient.

• Deal availability: 35.6% of listings are priced as good or great deals.
• Inventory: There are 6,523 listings available.
• Price trend: Prices have softened 11.55% compared with last year.
• Clean inventory: 73.9% of listings are accident-free.

If you find a listing below $22,440, 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 $22,440 sits slightly below last year's $25,370.

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 lower entry cost can reduce the amount of value left to lose over your ownership period.

The flip side is that resale strength will depend heavily on trim, condition, and equipment, especially because higher-spec versions carry much more value than base examples. Well-kept vehicles with desirable features should be easier to move later than stripped or poorly maintained ones.

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?

The 2021 Jeep Grand Cherokee earns five-star ratings from NHTSA with 4WD, but four-star ratings with 2WD because of a three-star rollover resistance rating. It also earns a Marginal driver rating and a Poor front-passenger rating in IIHS small-overlap frontal testing, and its headlights also rate Poor unless you upgrade to the HID setup with automatic high-beam assist.

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

Jeep does offer a strong driver-assistance suite on equipped trims, including 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. The backup camera, parking sensors, and ParkSense parking assistance system also add convenience.

The caution here is straightforward: the crash-test results are the main reason to be selective, and you should pay close attention to whether the exact vehicle you’re considering has the available safety equipment you want.

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:

• 35.6% of listings are priced as good or great deals.
• At 73.9% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.
• Price trend: Prices have softened 11.55% compared with last year.
• Owners rate it 4.62/5 — a strong satisfaction signal.
• It’s the last version of the current-generation two-row Grand Cherokee before the redesign arrives.

Consider the 2020 if:

• At $20,423, the 2020 costs less than the current year's $22,440 average.
• It remains a familiar, versatile SUV with strong off-road capability.

Consider the 2022 if:

• At $27,072, the 2022 costs more than the current year's $22,440 average.
• It brings a redesigned cabin with a major technology and sophistication upgrade.

The bottom line: If you want the familiar two-row Grand Cherokee and like the current market pricing, the 2021 is the sensible buy. If your priority is saving money, the 2020 is the better value play. If you want the newer design and tech, it makes more sense to stretch to the 2022.

These recommendations are based on CarGurus' proprietary market data from September 15, 2026, CarGurus experts' opinions, and generative AI.