Used 2021 Jeep Grand Cherokee for Sale near Chicago, IL
257 results
CarGurus Analysis:
2021 Jeep Grand Cherokee
With 255 currently listed for sale near Chicago, IL and an average price of $25,307.00, 50.6% 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 a stylish design, luxurious interior materials, and impressive off-road capability, making it an appealing choice for SUV buyers.
CarGurus Analysis: 2021 Jeep Grand Cherokee
overall
Summary
With 255 currently listed for sale near Chicago, IL and an average price of $25,307.00, 50.6% 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 a stylish design, luxurious interior materials, and impressive off-road capability, making it an appealing choice for SUV buyers.
Why it stands out
The 2021 Jeep Grand Cherokee represents a blend of utility and sophistication, appealing to a diverse range of drivers. Its timeless design continues to attract buyers, while its robust capabilities, especially off-road, ensure it maintains its rugged heritage. Owners appreciate the spacious interior and advanced technology options, but some express disappointment regarding certain features and fuel efficiency. With a user rating of 4.62 out of 5 stars, the Grand Cherokee enjoys a positive reputation among its owners. However, it's essential to consider that the competitive safety ratings, particularly from the IIHS, could be a deterrent for some buyers. The Grand Cherokee excels in performance, and its myriad trims offer both luxury and off-road variants that cater to different preferences. This SUV stands out as a well-rounded choice in its segment.
Other model years to consider
- Average price: $32,140.00
- Good/great deal percentage: 79.3%
- User rating: 5 / 5
- Total listings: 314
- Average price: $28,987.00
- Good/great deal percentage: 77.2%
- User rating: 4.86 / 5
- Total listings: 303
- Average price: $34,156.00
- Good/great deal percentage: 78.9%
- User rating: 5 / 5
- Total listings: 304
This analysis is based on CarGurus' proprietary market data from May 26, 2026, CarGurus experts' opinions, and generative AI.
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4.7 Overall rating
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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 |
|---|---|
| Overland 4WD | $51,230 |
| High Altitude 4WD | $54,175 |
| 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 Kenosha, WI: The city has the cheapest average price at $22,824, likely influenced by higher inventory levels (477 listings).
- High Prices in Overlapping Markets: Aurora, IL ($26,107) and Palatine, IL ($26,203) have higher average prices, suggesting either demand pressures or less aggressive pricing strategies.
- Stable Mid-Range Prices: Listings from cities like Milwaukee, WI (426 listings) maintain a moderately priced inventory around $23,735, illustrating a regional equilibrium.
City-Level Pricing
| City | Total Listings | Avg Price |
|---|---|---|
| Palatine, IL | 247 | $26,203 |
| Aurora, IL | 236 | $26,107 |
| Kenosha, WI | 477 | $22,824 |
| South Bend, IN | 434 | $23,389 |
| Rockford, IL | 437 | $22,542 |
| Milwaukee, WI | 426 | $23,735 |
| Janesville, WI | 426 | $24,222 |
| Holland, MI | 427 | $23,679 |
| Kalamazoo, MI | 428 | $23,792 |
| Lafayette, IN | 448 | $25,096 |
Pricing by Trim Packages
Key Insights
- High Inventory for Limited 4WD: The Limited 4WD (335 listings) is the most commonly listed trim, indicating strong market demand.
- Premium Pricing on Higher Trims: The Summit 4WD ($57,305 MSRP) commands a significant mark-up, reflecting luxury features that cater to a niche market.
- Value in the Limited RWD Trim: The Limited RWD presents a competitive price point at $41,560 MSRP for consumers looking for value without 4WD capabilities.
Trim-Level Details
| Trim | Listings | MSRP | Drivetrain | Engine |
|---|---|---|---|---|
| Limited 4WD | 335 | $43,580 | 4X4 | 3.6L 295 hp V6 |
| Overland 4WD | 236 | $51,230 | 4X4 | 3.6L 295 hp V6 |
| Summit 4WD | 134 | $57,305 | 4X4 | 3.6L 295 hp V6 |
| Limited RWD | 41 | $41,560 | 4X2 | 3.6L 295 hp V6 |
| Laredo E 4WD | 68 | $37,485 | 4X4 | 3.6L 295 hp V6 |
| Trailhawk 4WD | 56 | $46,815 | 4X4 | 3.6L 295 hp V6 |
Pricing Analysis by Model Year
Key Insights
- Strong Premium for New Models: The 2026 Jeep Grand Cherokee holds a substantial premium at $48,401, about 24.5% above MSRP, highlighting robust demand and potentially limited supply.
- Depreciation Trends: Significant depreciation appears in older models, with the 2017 year losing nearly 49.1% of its value compared to MSRP, indicating a steep value drop as vehicles age.
- More Stable Pricing for Recent Models: The 2022 model shows the best overall value with only 23.3% depreciation, representing a good balance between price and remaining features for shoppers.
Model Year Pricing
| Model Year | Original MSRP | Avg Price | Price vs MSRP |
|---|---|---|---|
| 2026 Jeep Grand Cherokee | $38,920 | $48,401 | +24.5% |
| 2025 Jeep Grand Cherokee | $37,095 | $38,775 | +4.5% |
| 2024 Jeep Grand Cherokee | $36,495 | $34,366 | -5.8% |
| 2023 Jeep Grand Cherokee | $39,535 | $32,327 | -18.2% |
| 2022 Jeep Grand Cherokee | $36,980 | $28,334 | -23.3% |
| 2020 Jeep Grand Cherokee | $32,150 | $22,471 | -30.0% |
| 2019 Jeep Grand Cherokee | $31,945 | $19,302 | -39.8% |
| 2018 Jeep Grand Cherokee | $30,895 | $19,854 | -35.8% |
| 2017 Jeep Grand Cherokee | $30,395 | $15,447 | -49.1% |
| 2016 Jeep Grand Cherokee | $29,995 | $12,959 | -56.8% |
| 2015 Jeep Grand Cherokee | $29,995 | $12,594 | -58.1% |
| 2014 Jeep Grand Cherokee | $29,495 | $11,607 | -60.6% |
These recommendations are based on CarGurus' proprietary market data from May 21, 2026, CarGurus experts' opinions, and generative AI.
