Used 2021 Jeep Grand Cherokee for Sale near Chicago, IL
252 results
CarGurus Analysis:
2021 Jeep Grand Cherokee
With 245 currently listed for sale near Chicago, IL and an average price of $26,606.00, 48.2% of 2021 Jeep Grand Cherokees for sale on CarGurus are rated as good or great deals.
Favorably reviewed: Owners rated the 2021 Jeep Grand Cherokee 4.62 / 5 stars.
100.0% of 2021 Grand Cherokee models on CarGurus are accident free.
The 2021 Jeep Grand Cherokee features impressive off-road capabilities, advanced technology, and a variety of trims to suit different preferences.
CarGurus Analysis: 2021 Jeep Grand Cherokee
overall
Summary
With 245 currently listed for sale near Chicago, IL and an average price of $26,606.00, 48.2% of 2021 Jeep Grand Cherokees for sale on CarGurus are rated as good or great deals.
Favorably reviewed: Owners rated the 2021 Jeep Grand Cherokee 4.62 / 5 stars.
100.0% of 2021 Grand Cherokee models on CarGurus are accident free.
The 2021 Jeep Grand Cherokee features impressive off-road capabilities, advanced technology, and a variety of trims to suit different preferences.
Why it stands out
The 2021 Jeep Grand Cherokee remains a standout in the midsize SUV segment, thanks to its perfect blend of rugged utility and upscale sophistication. Notable for its stylish design, the Grand Cherokee is equipped with a well-appointed interior that features premium materials and a wide array of tech options, making for a luxurious driving experience. What sets it apart from competitors is its impressive off-road capability, making it an excellent choice for adventurers and everyday users alike. The inclusion of advanced features like the Uconnect infotainment system enhances its appeal, providing seamless connectivity and navigation. However, some buyers may find the base engine underwhelming and the crash-test ratings from the IIHS concerning, especially since safety ratings can influence the purchasing decision. Overall, the Grand Cherokee offers a versatile platform that can satisfy many drivers' needs, blending features of mainstream, luxury, and performance SUVs into one package.
Other model years to consider
- Average price: $31,828.00
- Good/great deal percentage: 77.2%
- User rating: 5 / 5
- Total listings: 312
- Average price: $28,767.00
- Good/great deal percentage: 75.4%
- User rating: 4.86 / 5
- Total listings: 297
- Average price: $34,361.00
- Good/great deal percentage: 75.4%
- User rating: 5 / 5
- Total listings: 305
This analysis is based on CarGurus' proprietary market data from June 2, 2026, CarGurus experts' opinions, and generative AI.
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4.7 Overall rating
Filter by rating
Lee B
Reviewed a 2021 Jeep Grand Cherokee on May 7, 2026
Beautiful, solid, great stereo, comfortable seats, a high quality ride. Drives beautifully between 0 - 100 mph
Lee B
Reviewed a 2021 Jeep Grand Cherokee on May 7, 2026
Beautiful, solid, great stereo, comfortable seats, a high quality ride. Drives beautifully between 0 - 100 mph. No shakes or rattles. Very quiet cabin.
James H
Reviewed a 2021 Jeep Grand Cherokee on Apr 21, 2025
I'm a little biased because I've always driven Grand Cherokees. But I've always done that for a reason. Good quality, good features, great 4x4 capabilities and great handling.
Anonymous
Reviewed a 2021 Jeep Grand Cherokee on Aug 31, 2024
This vehicle is exactly what I expected from the Jeep brand . It has some great features, including panoramic sunroof. It would have been nice to have a CD player or a hard drive that holds CD recordings.
2021 Jeep Grand Cherokee Trims
| Trim type | MSRP |
|---|---|
| High Altitude 4WD | $54,175 |
| Overland 4WD | $51,230 |
| Trailhawk 4WD | $46,815 |
| Laredo X RWD | $38,960 |
| Laredo E 4WD | $37,485 |
| 80th Anniversary Edition 4WD | $45,970 |
| Laredo X 4WD | $40,985 |
| Limited 4WD | $43,580 |
2021 Jeep Grand Cherokee Price Trends
CarGurus tracks the prices of millions of used car listings every year. See how the average price of 2021 Jeep Grand Cherokee prices has changed over time.
See more price trends2021 Jeep Grand Cherokee Pricing Analysis: Chicago, IL Market Report
Pricing by Nearby Locations
Market Area: Chicago, IL
Key Insights
- Lowest Prices in South Bend: The average price of $21,862 in South Bend, IN suggests a more price-sensitive market, possibly due to higher inventory or less competitive demand.
- Higher Prices in Suburbs: Areas like Palatine and Aurora ($26,513) show the highest average prices, indicating stronger demand in suburban markets.
- Varied Inventory Levels: The inventory ranges widely, with Kenosha, WI having the highest at 483 listings, suggesting stable supply which could help moderate prices.
City-Level Pricing
| City | Total Listings | Avg Price |
|---|---|---|
| Palatine, IL | 251 | $26,513 |
| Aurora, IL | 245 | $26,513 |
| Lafayette, IN | 431 | $26,123 |
| Holland, MI | 420 | $24,121 |
| Kalamazoo, MI | 418 | $23,581 |
| Janesville, WI | 414 | $23,526 |
| Milwaukee, WI | 408 | $22,934 |
| Rockford, IL | 427 | $22,904 |
| Kenosha, WI | 483 | $23,097 |
| South Bend, IN | 419 | $21,862 |
Pricing by Trim Packages
Key Insights
- Dominance of the Limited 4WD Trim: The Limited 4WD trim leads with 398 listings, indicating strong market visibility and demand as a benchmark for pricing.
- Premium Models Command Higher MSRP: The Summit 4WD trim, priced at $57,305, reflects a significant $24,725 gap compared to the Limited 4WD, emphasizing the price premium for luxury features.
- Greater Variety in Drivetrain: The diversity in drivetrains (4X2 vs 4X4) among trims may cater to different consumer preferences such as performance vs fuel efficiency.
Trim-Level Details
| Trim | Listings | MSRP | Drivetrain | Engine |
|---|---|---|---|---|
| Limited 4WD | 398 | $43,580 | 4X4 | 3.6L 295 hp V6 |
| Overland 4WD | 272 | $51,230 | 4X4 | 3.6L 295 hp V6 |
| Summit 4WD | 157 | $57,305 | 4X4 | 3.6L 295 hp V6 |
| Limited RWD | 40 | $41,560 | 4X2 | 3.6L 295 hp V6 |
| Laredo E 4WD | 57 | $37,485 | 4X4 | 3.6L 295 hp V6 |
| Trailhawk 4WD | 64 | $46,815 | 4X4 | 3.6L 295 hp V6 |
Pricing Analysis by Model Year
Key Insights
- 2025 Model Experiencing Strong Demand: The latest year, 2026, shows a price of $46,971, which is +20.6% over its MSRP, indicating robust demand for newer models.
- Deep Depreciation for Older Models: The 2014 model has declined to $11,519, revealing an -60.0% drop compared to its original MSRP, illustrating significant depreciation over time.
- 2022 Models Present Attractive Options: The 2022 Jeep Grand Cherokee is averaging $28,789, just -22.4% below MSRP, making it a favorable choice for value-conscious buyers looking for more recent models.
Model Year Pricing
| Model Year | Original MSRP | Avg Price | Price vs MSRP |
|---|---|---|---|
| 2026 Jeep Grand Cherokee | $38,920 | $46,971 | +20.6% |
| 2025 Jeep Grand Cherokee | $37,095 | $38,722 | +4.4% |
| 2024 Jeep Grand Cherokee | $36,495 | $34,262 | -6.1% |
| 2023 Jeep Grand Cherokee | $39,535 | $31,837 | -19.5% |
| 2022 Jeep Grand Cherokee | $36,980 | $28,789 | -22.4% |
| 2020 Jeep Grand Cherokee | $32,150 | $22,723 | -29.4% |
| 2019 Jeep Grand Cherokee | $31,945 | $19,344 | -39.5% |
| 2018 Jeep Grand Cherokee | $30,895 | $32,658 | +5.7% |
| 2017 Jeep Grand Cherokee | $30,395 | $16,541 | -45.5% |
| 2016 Jeep Grand Cherokee | $29,995 | $13,287 | -55.7% |
| 2015 Jeep Grand Cherokee | $29,995 | $13,877 | -53.7% |
| 2014 Jeep Grand Cherokee | $29,495 | $11,519 | -60.0% |
These recommendations are based on CarGurus' proprietary market data from June 4, 2026, CarGurus experts' opinions, and generative AI.
