Used 2016 Jeep Grand Cherokee for Sale near Chicago, IL
191 results
CarGurus Analysis:
2016 Jeep Grand Cherokee
With 364 currently listed for sale near Chicago, IL and an average price of $13,511.00, 23.1% of 2016 Jeep Grand Cherokees for sale on CarGurus are rated as good or great deals.
Favorably reviewed: Owners rated the 2016 Jeep Grand Cherokee 4.8 / 5 stars.
65.4% of 2016 Grand Cherokee models on CarGurus are accident free.
The 2016 Jeep Grand Cherokee is known for its powerful performance, luxurious features, and off-road capabilities, making it an excellent choice for both daily driving and rugged adventures.
CarGurus Analysis: 2016 Jeep Grand Cherokee
overall
Summary
With 364 currently listed for sale near Chicago, IL and an average price of $13,511.00, 23.1% of 2016 Jeep Grand Cherokees for sale on CarGurus are rated as good or great deals.
Favorably reviewed: Owners rated the 2016 Jeep Grand Cherokee 4.8 / 5 stars.
65.4% of 2016 Grand Cherokee models on CarGurus are accident free.
The 2016 Jeep Grand Cherokee is known for its powerful performance, luxurious features, and off-road capabilities, making it an excellent choice for both daily driving and rugged adventures.
Why it stands out
The 2016 Jeep Grand Cherokee distinguishes itself with its combination of luxury and ruggedness. It appeals to buyers who need a vehicle that can handle towing and off-road excursions, as well as those who simply enjoy the iconic styling of the Jeep brand. Its adeptness for both on-road comfort and off-road capability is especially highlighted by various available trims, including the powerful SRT model designed for performance. However, while it excels in many areas—such as interior comfort, spaciousness, and accessible technology—it isn't without its downsides. Some owners have noted the absence of certain features, such as a CD player, and the presence of a truck-like ride quality can detract from the everyday driving experience. Overall, the Grand Cherokee offers a well-rounded package that balances style, performance, and utilitarian capability for adventurers and families alike.
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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4.8 Overall rating
Filter by rating
Thomas T
Reviewed a 2016 Jeep Laredo 75th Anniversary 4WD on Jan 20, 2025
After driving it for the first time I knew I wanted it. I had to have some things line up for me to be able to buy it but they did and I was able to bring it home. The style, comfort and luxury are more than I ever could’ve asked for.
Russ E
Reviewed a 2016 Jeep Grand Cherokee on Jan 19, 2026
Rides and handles great. The 3.0L diesel runs awesome and gets excellent fuel mileage. Can't hear the diesel at all on the road. The looks of the GC are so sexy!
Ken N
Reviewed a 2016 Jeep Limited on Oct 22, 2025
The car is nice I like the black and it’s clean it has a back up camera even though I don’t use them that’s nice as well it’s very spacious
Cory L
Reviewed a 2016 Jeep Grand Cherokee on Feb 11, 2020
2016 Jeep Cherokee - great everyday vehicle. Super comfortable and great capabilities. 4x4 with all the comfort of a fine leather chair. Mudd/rocks no problem. Highway driving @ 80 mph no problem. Plenty of space for all my sh...stuff. :) This is our fourth GC and fifth Jeep overall. No complaints.
2016 Jeep Grand Cherokee Trims
| Trim type | MSRP |
|---|---|
| Laredo | $29,995 |
| High Altitude 4WD | $50,090 |
| Limited 75th Anniversary 4WD | $43,175 |
| Summit 4WD | $52,795 |
| Limited | $37,565 |
| Overland 4WD | $47,395 |
| Laredo 4WD | $32,295 |
| Limited 4WD | $39,565 |
2016 Jeep Grand Cherokee Price Trends
CarGurus tracks the prices of millions of used car listings every year. See how the average price of 2016 Jeep Grand Cherokee prices has changed over time.
See more price trends2016 Jeep Grand Cherokee Pricing Analysis: Chicago, IL Market Report
Pricing by Nearby Locations
Market Area: Chicago, IL
Key Insights
- Lower Prices in Milwaukee: The city of Kalamazoo, MI ($11,473) offers the lowest average price, suggesting high inventory and potentially lower demand.
- Higher Prices in South Bend: In contrast, South Bend, IN ($13,900) commands the highest price among nearby locations, indicating a preference for these vehicles in the area.
- Market Dynamics Reflect Inventory Levels: Cities with greater listings, such as Kenosha, WI (326 listings), demonstrate more competitive pricing, reflecting strong competition among sellers.
City-Level Pricing
| City | Total Listings | Avg Price |
|---|---|---|
| Kalamazoo, MI | 281 | $11,473 |
| Rockford, IL | 285 | $11,996 |
| Kenosha, WI | 326 | $13,264 |
| Aurora, IL | 186 | $13,072 |
| Palatine, IL | 189 | $13,194 |
| Janesville, WI | 280 | $12,818 |
| Milwaukee, WI | 278 | $13,879 |
| South Bend, IN | 283 | $13,900 |
| Holland, MI | 272 | $13,900 |
| Lafayette, IN | 296 | $13,485 |
Pricing by Trim Packages
Key Insights
- Most Popular Trim: The Limited 4WD (395 listings) is the most commonly available trim, reflecting strong demand and balance of features.
- Price Range Across Trims: The Summit 4WD ($52,795 MSRP) is the highest-priced trim, while the Laredo ($29,995 MSRP) offers the most budget-friendly option.
- Four-Wheel Drive Dominance: All trims listed are 4WD, indicating a strong consumer preference for off-road capability among buyers in the Chicago area.
Trim-Level Details
| Trim | Listings | MSRP | Drivetrain | Engine |
|---|---|---|---|---|
| Limited 4WD | 395 | $39,565 | 4X4 | 3.6L 295 hp V6 |
| Laredo 4WD | 245 | $32,295 | 4X4 | 3.6L 295 hp V6 |
| Overland 4WD | 272 | $47,395 | 4X4 | 3.6L 295 hp V6 |
| Summit 4WD | 157 | $52,795 | 4X4 | 3.6L 295 hp V6 |
| Laredo E 4WD | 57 | $34,295 | 4X4 | 3.6L 295 hp V6 |
| Limited | 40 | $37,565 | 4X2 | 3.6L 295 hp V6 |
| High Altitude 4WD | 68 | $50,090 | 4X4 | 3.6L 295 hp V6 |
| Laredo | 33 | $29,995 | 4X2 | 3.6L 295 hp V6 |
Pricing Analysis by Model Year
Key Insights
- Notable Appreciation for Newer Models: The 2026 Jeep Grand Cherokee currently has an average price of $46,971, indicating a strong demand or limited supply as it is priced 20.6% above MSRP.
- Continuous Depreciation Trend: The 2017 model has depreciated the most, with an average price of $16,541, a decrease of 45.5% vs MSRP.
- Value Proposition in 2022-2020 Models: These model years maintain a good balance of price and equipment, with depreciation in the range of 20.8% to 28.9%, making them attractive for buyers seeking moderate discounts.
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 | -22.2% |
| 2021 Jeep Grand Cherokee | $35,460 | $26,368 | -25.7% |
| 2020 Jeep Grand Cherokee | $32,150 | $22,723 | -29.4% |
| 2019 Jeep Grand Cherokee | $31,945 | $19,344 | -39.4% |
| 2018 Jeep Grand Cherokee | $30,895 | $32,658 | +5.7% |
| 2017 Jeep Grand Cherokee | $30,395 | $16,541 | -45.5% |
| 2015 Jeep Grand Cherokee | $29,995 | $13,877 | -53.8% |
| 2014 Jeep Grand Cherokee | $29,495 | $11,519 | -60.9% |
These recommendations are based on CarGurus' proprietary market data from June 4, 2026, CarGurus experts' opinions, and generative AI.
