Used 2021 Jeep Grand Cherokee for Sale nearChicago, IL

How much does the 2021 Jeep Grand Cherokee cost?

Prices have softened 11.18% compared to this time last year, making it a favorable time to shop this model year.

With 6,483 listings available, you have a solid amount of inventory to compare across trims and conditions.

If you find a listing below $22,720.86, 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 — the 4.62/5 user rating points to strong owner satisfaction, and the expert rating is 7.17/10. 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. The model also fits buyers who want a familiar two-row Grand Cherokee rather than the newer, larger interpretation of the name.

The trade-offs are clear: the base engine is underwhelming, and some owners feel the tech and premium features do not fully match the price. The expert review also notes that the interior is aging and that some fit-and-finish details feel overdue for a redesign.

With 29.8% of listings marked as good or great deals, you still have room 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 vehicle that many drivers find dependable enough to live with day after day, with repeated praise for its smooth ride, strong power, and overall value. That kind of feedback suggests you can count on it for regular use if you choose a well-kept example.

The expert review adds that the Grand Cherokee feels capable and well suited to adventure, with a drivetrain and chassis setup that inspire confidence in daily driving and off-road use. Jeep’s free scheduled maintenance for the first three years and 36,000 miles also helps reduce early ownership burden.

For used buyers, the main long-term risk is that condition and maintenance history matter a lot, especially given the model’s age and mixed safety record.

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

At 74% 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 is priced aggressively. Pay close attention to bodywork quality, panel alignment, tire wear, and signs of prior repair, since accident history can affect both value and long-term ownership confidence.

Key things to evaluate:

• Trim level: The affordable Laredo and Limited trims sit below the upscale Overland and Summit, while Trailhawk is the serious off-road choice and SRT and Trackhawk are the performance models. Base trims miss some of the premium feel and equipment that make higher trims more appealing.
• 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: ProTech II 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. Some safety features are not standard on every trim.
• Infotainment: Uconnect 4C with Nav includes navigation, Apple CarPlay, Android Auto, a 4G LTE WiFi hotspot, and Jeep Skill for Amazon Alexa. The system is responsive and easy to use.
• 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, and Summit.

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 rest of the lineup.
• Limited: This is the best-value choice for many shoppers because it adds more of the comfort and convenience that make the Grand Cherokee feel upscale without jumping all the way to luxury pricing.
• Laredo X: This is a value-oriented variant that builds on the lower trims while keeping the lineup accessible.
• 80th Anniversary Edition: This is a celebratory variant for shoppers who want a little more distinction without moving into the upper luxury trims.
• Overland: This is the step up for buyers who want a more premium experience and are willing to pay for it.
• Summit: This is the luxury pick, with the richest interior presentation and the most polished feel in the lineup.
• Trailhawk: This is the one to buy if off-road use matters most, since it is the serious adventure-focused trim.
• SRT and Trackhawk: These are the performance-focused choices for buyers who want the most aggressive driving character.

The safety package is strongest on higher trims, so if advanced driver assistance matters to you, verify equipment carefully before you buy.

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 are patient and condition-focused.

• Deal availability: 29.8% of listings are priced as good or great deals.
• Inventory: There are 6,483 listings available.
• Price trend: Prices have softened 11.18% compared with last year.
• Clean inventory: 74.0% of listings are accident-free.

If you find a listing below $22,720.86, 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 $22,712 sits slightly below last year's $25,572.

That price movement suggests the market has already adjusted downward, which can help you buy more confidently now. For a future seller, it also means you should expect resale value to depend heavily on condition, trim, and equipment rather than on broad market appreciation.

Well-kept examples with desirable features should hold buyer interest better than rougher or lightly equipped ones. Strong owner satisfaction also helps support demand when it is time to sell.

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 a five-star overall rating from NHTSA in 4WD form, while 2WD versions drop to four-star overall 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 the 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.

The available 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. Jeep also includes a backup camera with guidance lines, parking sensors, and ParkSense parking assistance.

The main caveat is the weak IIHS performance, which is the biggest safety drawback you should weigh before buying.

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:

• 29.8% of listings are priced as good or great deals.
• At 74% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.
• Price trend: Prices have softened 11.18% compared with last year.
• Owners rate it 4.62/5 — a strong satisfaction signal.
• It is the final version of the current-generation two-row Grand Cherokee before the redesign arrives.

Consider the 2020 if:

• At $20,632, the 2020 costs less than the current year's $22,712 average.
• It is a long-running version that still offers broad capability and familiar Grand Cherokee appeal.

Consider the 2022 if:

• At $27,608, the 2022 costs more than the current year's $22,712 average.
• It brings a redesigned layout with a noticeable step up in technology and sophistication.

The bottom line: If you want the familiar two-row Grand Cherokee and like the idea of shopping a softened market, the 2021 is the sensible pick. If price matters most, the 2020 gives you a lower entry point, while the 2022 makes sense if you want the redesign and are willing to pay more for it.

These recommendations are based on CarGurus' proprietary market data from August 28, 2026, CarGurus experts' opinions, and generative AI.