Used 2016 Jeep Cherokee for Sale nearChicago, IL

How much does the 2016 Jeep Cherokee cost?

Prices have softened 8.87% compared to this time last year, making it a favorable time to shop this model year.

There are 2,372 listings available, which gives you a solid pool of options to compare.

Is the 2016 Jeep Cherokee a good car?

Generally — 4.1/5 — the 2016 Jeep Cherokee is a strong fit if you want a compact SUV that blends comfort, utility, and capability. The expert rating is 7.8/10, and the model scores 9/10 across Look and feel and Technology.

Drivers repeatedly praise its sporty feel, comfortable interior, adequate power, and convenient size, along with features like heated seats and a heated steering wheel. The overview also points to a vehicle that can handle daily commuting, freeway ramps, and rougher pavement while still being useful for a wide range of tasks.

That combination makes it especially appealing if you want one SUV that can do everyday duty without giving up a more adventurous side. The market also shows 30.8% good or great deals, which suggests there are worthwhile opportunities if you shop carefully.

Is the 2016 Jeep Cherokee reliable?

Owners rate it 4.1/5, a solid signal of long-term satisfaction.

User feedback points to a dependable-feeling ownership experience for many drivers, with praise for the Cherokee’s comfortable interior and useful features. At the same time, the summary also flags concerns about engine and transmission reliability, which is worth taking seriously when you’re shopping used.

The expert drive notes also call out reliability concerns tied to the 9-speed automatic transmission, while the ownership-cost discussion says negative ratings may not reflect the full dependability picture. If you buy one, long-term ownership risk is most likely to come from transmission behavior and maintenance history, so condition and service records matter a lot.

What should I look for when buying a used 2016 Jeep Cherokee?

At 60.8% 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 price looks unusually attractive. Focus on body condition, signs of prior repair, and whether the drivetrain and electronics behave as they should during a thorough test drive.

Key things to evaluate:

• Trim level: The Trailhawk is the rugged, “Trail Rated” version, with a more aggressive look, revised bumpers, and hardware that improves approach and departure angles. Base trims are more about everyday use, so you should pay close attention to which features and off-road pieces are actually included.
• Powertrain: The standard 2.4-liter four-cylinder is paired with a 9-speed automatic, while the optional 3.2-liter V6 is described as the better choice and is more efficient on the highway in Trailhawk form. The transmission’s behavior is a recurring concern, so test it carefully.
• Safety package: The Cherokee includes a standard Park View reversing camera, and available driver aids include blind-spot warning with rear cross-traffic alert, lane-departure warning, and forward-collision warning with automatic emergency braking. Some of these features are optional rather than standard, so verify the exact equipment on the listing you’re considering.
• Infotainment: Trailhawk models use Uconnect 8.4 with an 8.4-inch touchscreen, USB and SD card ports, Bluetooth calling and music streaming, Siri Eyes Free, Do Not Disturb, and text-message reply features. Navigation is optional, and Uconnect Access services are subscription-based.
• Fuel efficiency: The V6 is described as matching the 4-cylinder’s 22-mpg combined rating in Trailhawk form, and the expert drive notes that real-world mileage can fall short of EPA estimates.

Which 2016 Jeep Cherokee trim should I buy?

The 2016 Jeep Cherokee is offered in 4 trim levels: Sport, Latitude, Limited, Trailhawk.

Here's the short version:

• Sport: This is the entry point, so it makes sense if you want the Cherokee’s basic capability and styling at the lowest price, but you should expect the fewest features.
• Latitude: This is the trim that most buyers will likely find easiest to live with, since it sits above the base model without jumping all the way to the more specialized Trailhawk.
• Limited: This is the upscale choice if you want a more premium-feeling Cherokee with more comfort and convenience equipment.
• Trailhawk: This is the best-value trim if you want the Cherokee’s full personality, because it adds the rugged hardware, off-road-focused tuning, and the most distinctive capability in the lineup.

The safety content also notes that the standard reversing camera is weak in low light, so if you’re shopping any trim, make sure the available driver-assistance features are present if they matter to you.

Is now a good time to buy a used 2016 Jeep Cherokee?

This is a moderate market for selective buyers, so you can shop with some leverage if you’re patient and compare listings carefully.

• Deal availability: 30.8% of listings are priced as good or great deals.
• Inventory: There are 2,372 listings available.
• Price trend: Prices have softened 8.87% compared with last year.
• Clean inventory: 60.8% of listings are accident-free.

If you find a listing below $10,053, that's toward the low end of the year-round range and worth acting on quickly.

What is the 2016 Jeep Cherokee's resale value?

The current average of $10,053 sits slightly below last year's $11,032.

That tells you the Cherokee has moved into a softer pricing environment, which can help you as a buyer but may limit upside if you plan to resell soon. If you buy at the right price and keep the vehicle in strong condition, you can reduce the impact of that depreciation.

The model’s broad appeal also helps support future demand, especially because it combines comfort, utility, and capability in a way that many shoppers still want. Vehicles with solid owner satisfaction ratings, like this model year's 4.1/5, tend to retain buyer demand, which supports resale value over time.

Is the 2016 Jeep Cherokee safe?

The 2016 Jeep Cherokee earns a four-star overall rating from NHTSA, and the IIHS rates it Marginal in the small overlap frontal impact test while giving it Good ratings in all other assessments and a Superior rating for front crash prevention.

It earns a 6/10 safety score from our experts.

Jeep equips the Cherokee with a standard Park View reversing camera, and available safety tech includes blind-spot warning with rear cross-traffic alert, lane-departure warning, and forward-collision warning with automatic emergency braking. The weak low-light camera performance and the Marginal IIHS result are the main caveats to keep in mind.

Should I buy a 2016 Jeep Cherokee or consider a different year?

If you're weighing the 2016 against nearby model years, here's how to think about it:

Choose the 2016 if:

• 30.8% of listings are priced as good or great deals.
• At 60.8% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.
• Price trend: Prices have softened 8.87% compared with last year.
• Owners rate it 4.1/5 — a solid satisfaction signal.
• The expert drive highlights the Trailhawk’s ability to handle both daily driving and serious off-pavement use while still feeling comfortable and composed.

The bottom line: The 2016 Cherokee makes sense if you want a capable, comfortable compact SUV and you’re willing to shop carefully for condition and history. If you’re more price-sensitive, you may want to compare nearby model years and focus on the cleanest, best-maintained example rather than chasing the lowest sticker price.

How does the 2016 Jeep Cherokee compare to the 2016 Ford Escape?

Our experts score the 2016 Jeep Cherokee 7.8/10 and the 2016 Ford Escape 7.2/10.

The Cherokee brings stronger personality and more off-pavement capability, while the Escape is the more conventional choice. The Cherokee also has the higher expert score, but the Escape undercuts it on average used price and offers more listings to shop from. If you want a more adventurous compact SUV, the Cherokee is the better fit; if you want a broader pool of cheaper options, the Escape is worth a look.

These recommendations are based on CarGurus' proprietary market data from November 10, 2026, CarGurus experts' opinions, and generative AI.