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 luxurious models, all featuring robust performance and advanced technology.

• Starting at $18,408
• 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: $18,408 (updated weekly)
• MPG/MPGe: 18 city / 25 hwy
• Inventory: 76 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 luxury features without a significant price jump.

• Avg. market price: $22,444 (updated weekly)
• MPG/MPGe: 18 city / 25 hwy
• Inventory: 85 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 fuel efficiency and comfort.

• Avg. market price: $24,736 (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 choice.

• Avg. market price: $20,927 (updated weekly)
• MPG/MPGe: 18 city / 25 hwy
• Inventory: 394 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 premium features and off-road capability.

• Avg. market price: $24,571 (updated weekly)
• MPG/MPGe: 18 city / 25 hwy
• Inventory: 249 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, ready for any adventure.

• Avg. market price: $29,048 (updated weekly)
• MPG/MPGe: 18 city / 25 hwy
• Inventory: 156 listings — widest selection in the lineup
• View Summit 4WD listings

Trim Recommendations

Most Popular — Limited 4WD

With 394 active listings, the Limited 4WD is the clear volume leader in the lineup.

Browse Limited 4WD listings

Best Budget Option — Laredo E 4WD

At $18,408 avg market price — below the lineup median of $23,507 — 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 2021 Jeep Grand Cherokee cost?

Prices have softened 11.63% compared to this time last year, making it a favorable time to shop this model year.

There are 6,326 listings available, which suggests solid inventory for comparison shopping.

Is the 2021 Jeep Grand Cherokee a good car?

Yes — with a 4.6/5 user rating and a 7.2/10 expert rating, the 2021 Jeep Grand Cherokee lands as a strong choice for shoppers who want style and capability. The standout strength is Look and feel at 9/10.

Owners repeatedly praise its spacious interior, smooth ride, and impressive power, and they also point to its luxury feel and advanced technology features. The trade-offs are familiar for this model year: some owners mention missing tech features for the price, and gas mileage comes up as a drawback. That lines up with the overview, which frames this as a two-row SUV best suited to you if you value style, comfort, and driving character more than maximum efficiency or a long list of standard equipment.

The market also looks reasonably supportive, with 35.0% of listings marked as good or great deals.

Is the 2021 Jeep Grand Cherokee reliable?

Owners rate it 4.6/5, a strong signal of long-term satisfaction.

Owner feedback points to a vehicle that many drivers find dependable, with praise for its smooth ride, strong power, and overall satisfaction over time. The expert review also notes that Jeep’s ownership program includes free scheduled maintenance for the first three years and 36,000 miles, which helps reduce early ownership costs. For used buyers, the main long-term risk is that age-related wear and uneven maintenance history can matter more here than on a newer redesign.

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

At 73.2% 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 close inspection of bodywork, panel alignment, and any signs of prior repair. Because this model has known safety and age-related concerns, it makes sense to focus on condition, maintenance records, and whether the equipment on the specific listing matches what you expect. If you’re comparing multiple examples, the cleanest history and best-documented service record should carry extra weight.

Key things to evaluate:

• Trim level: The lineup spans affordable Laredo and Limited trims, upscale Overland and Summit trims, plus Trailhawk, SRT, and Trackhawk variants. The base trims are the most value-focused, while the higher trims add more premium materials and equipment.
• Powertrain: The standard 3.6-liter V6 makes 295 horsepower and 260 pound-feet of torque and is paired with an eight-speed automatic. An optional 5.7-liter Hemi V8 makes 360 hp and 390 lb-ft of torque, adds stronger towing capability, and brings more muscle at the cost of efficiency.
• Safety package: Jeep offers ProTech II Package features 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. These features are not standard across the lineup.
• Infotainment: The Uconnect 4C with Nav system includes navigation, Apple CarPlay, Android Auto, a 4G LTE WiFi hotspot, and Jeep Skill for Amazon Alexa. It is described as responsive and easy to use.
• Fuel efficiency: The V8 is described as returning no more than 17 mpg in combined driving, and the review notes that gas mileage is a weakness overall.

Which 2021 Jeep Grand Cherokee trim should I buy?

The 2021 Jeep Grand Cherokee is offered in 7 trim levels: Laredo, Limited, Overland, Summit, Trailhawk, SRT, Trackhawk.

Here's the short version:

• Laredo: This is the value-oriented starting point, and it makes sense if you want the Grand Cherokee formula without paying for extra luxury or specialty equipment.
• Limited: This is the best-value trim for most shoppers because it adds more comfort and convenience while staying on the more affordable side of the lineup.
• Overland: Choose this if you want a more upscale feel and more premium equipment without jumping all the way to the top of the range.
• Summit: This is the luxury-leaning choice, with the richest materials and the most polished cabin presentation in the lineup.
• Trailhawk: Pick this if you want the most serious off-road focus in the standard lineup.
• SRT: This is the performance-oriented choice for buyers who want a track-ready character.
• Trackhawk: This is the most extreme performance model, aimed at shoppers who want the highest-output version of the Grand Cherokee.

The safety package is not standard on every trim, so you should verify whether the specific listing includes the driver-assistance equipment you want.

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

This looks like a moderate, selective buyer’s market, so you have room to shop carefully without expecting every listing to be a bargain.

• Deal availability: 35.0% of listings are priced as good or great deals.
• Inventory: There are 6,326 listings available.
• Price trend: Prices have softened 11.63% compared with last year.
• Clean inventory: 73.2% of listings are accident-free.

If you find a listing below $21,903, 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 $21,903 sits slightly below last year's $24,785.

That decline suggests the market has already adjusted downward, which can help you buy at a more favorable entry point today. For a future seller, the current pricing trend means resale value may remain under pressure if the model continues to age without the same appeal as newer rivals. Still, a well-kept example with strong equipment and a clean history should hold up better than a neglected one.

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 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 ratings because of a three-star rollover resistance rating.

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

Jeep offers a strong list of available driver-assistance features through the ProTech II Package, 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 catch is that these features are not standard, and the IIHS results are a major weakness: the Grand Cherokee 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.

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:

• 35.0% of listings are priced as good or great deals.
• At 73.2% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.
• Price trend: Prices have softened 11.63% compared with last year.
• Owners rate it 4.6/5 — a strong satisfaction signal.
• It is the outgoing two-row Grand Cherokee, so you get the familiar formula before the redesign.

Consider the 2020 if:

• At $19,920, the 2020 costs less than the current year's $21,903 average.
• It offers a versatile midsize SUV with stylish design and off-road capability.

Consider the 2022 if:

• At $26,162, the 2022 costs more than the current year's $21,903 average.
• It brings a redesigned package with more technology and sophistication.

The bottom line: If you want the familiar Grand Cherokee experience at a softer price, the 2021 is the sweet spot. If your priority is saving money, the 2020 is the better value play; if you want the newer design and added tech, move up to the 2022.

How does the 2021 Jeep Grand Cherokee compare to the 2021 Ford Explorer?

Expert Pros & Cons (per CarGurus review team)

2021 Jeep Grand Cherokee:

• Pros: Stylish design, Premium interior materials, Great handling.
• Cons: Underwhelming base engine, Advanced safety features are not standard.

2021 Ford Explorer:

• Pros: Multiple powertrain options, Great handling, Spacious third row.
• Cons: Interior materials feel cheap, Advanced safety features are not standard.

Our experts score the 2021 Jeep Grand Cherokee 7.2/10 and the 2021 Ford Explorer 7.5/10. The Explorer edges ahead on expert score and gives you multiple powertrain options plus a spacious third row, while the Grand Cherokee counters with a more stylish design and better interior materials. If you care most about a premium feel and sharp handling, the Jeep is the more appealing pick; if you want more family flexibility, the Ford has the advantage.

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.