Used 2021 Toyota Highlander for Sale nearChicago, IL

How much does the 2021 Toyota Highlander cost?

Prices have softened 5.23% compared to this time last year, making it a favorable time to shop this model year.

There are 3,478 listings available, which suggests solid inventory for comparison shopping.

Is the 2021 Toyota Highlander a good car?

Yes — the 2021 Toyota Highlander earns a 4.9/5 user rating and a 7.5/10 expert rating. The standout strength is Safety at 10/10.

Drivers consistently praise its comfort, reliability, and features, and they also highlight the smooth ride, high-quality interior, spaciousness, and safety features. That lines up with the Highlander’s family-focused role in the overview, where comfort, space, and safety matter more than flash.

The trade-offs are familiar: the base engine is underwhelming, the styling is uninspired, and the technology feels outdated. Even so, the Highlander’s practical strengths make it a strong fit if you want a mainstream three-row SUV that prioritizes everyday usability.

The current market shows 37.0% good or great deals, so there are still some attractive listings to find.

Is the 2021 Toyota Highlander reliable?

Owners rate it 4.9/5, a strong signal of long-term satisfaction.

User feedback points to reliability, comfort, and features as recurring strengths, and many owners describe the Highlander as a vehicle they can count on. The expert review also emphasizes smooth, predictable operation and a reputation for reliability, which reinforces that dependable character.

Toyota’s safety and convenience package adds to the sense of low-stress ownership, and the model’s family-oriented design supports everyday durability. For used buyers, the main long-term risk is less about outright dependability and more about finding a well-kept example with consistent maintenance and no hidden wear.

What should I look for when buying a used 2021 Toyota Highlander?

At 74.6% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.

You should start with a vehicle history report and confirm whether any prior damage was repaired properly. A pre-purchase inspection is especially important on a three-row SUV like this, where family use can mean heavier wear on the interior, suspension, and safety systems. Focus on condition, maintenance records, and how well the technology and seating functions operate.

Key things to evaluate:

• Trim level: The lineup ranges from the LE through the Platinum, with the XSE adding a more aggressive front end, suspension tuning, and an appearance package. The Limited trim sits just below Platinum and brings a more upscale feel, while lower trims use the smaller 8-inch touchscreen.
• Powertrain: Every Highlander uses a 3.5-liter V6 with 295 horsepower and an eight-speed automatic transmission, with front-wheel drive or all-wheel drive available. The setup is smooth and predictable, but it is not built for quick acceleration.
• Safety package: Toyota Safety Sense 2.5+ includes automatic emergency braking with pedestrian detection and intersection support, plus road-sign assist, adaptive cruise control, lane-departure warning, lane-keeping assist, lane-tracing assist, and automatic high beams. These features are standard across the lineup.
• Infotainment: Lower trims get an 8-inch touchscreen, while the Limited offers a 12.3-inch screen as an option and the Platinum makes it standard. Android Auto and Apple CarPlay are standard, and the system is easy to use.
• Fuel efficiency: The V6 is rated at 21 mpg city and 29 mpg highway with front-wheel drive, or 20 mpg city and 27 mpg highway with all-wheel drive.

Which 2021 Toyota Highlander trim should I buy?

The 2021 Toyota Highlander is offered in 6 trim levels: LE, XLE, XSE, Limited, Platinum, and Limited trim.

Here's the short version:

• LE: This is the entry point, so it makes sense if you want the Highlander’s core comfort, space, and safety without paying for extras. It is the value play if you mainly want the family-hauling basics.
• XLE: This trim adds more equipment and is a sensible step up if you want a better-balanced daily driver without jumping too far in price. It should suit shoppers who want a more complete feature set.
• XSE: This is the sportier-looking choice, with a more aggressive front end, suspension tuning, and an appearance package. It is for buyers who want a little more style and a slightly firmer feel.
• Limited: This is the best-value trim for many shoppers because it brings a more upscale cabin and sits just below Platinum. It is the sweet spot if you want a premium feel without going all the way to the top.
• Platinum: This is the top-tier choice if you want the biggest touchscreen and the most upscale presentation. It makes the most sense if you want the most features available.
• Limited trim: This trim is called out as the test vehicle and is described as especially upscale inside, with near-flawless fit and finish. It suits buyers who care most about cabin quality and comfort.

Toyota Safety Sense 2.5+ is standard, so even lower trims get the core safety suite.

Is now a good time to buy a used 2021 Toyota Highlander?

This looks like a moderate, selective buyer’s market, with enough inventory and deal activity to reward careful shoppers.

• Deal availability: 37.0% of listings are priced as good or great deals.
• Inventory: There are 3,478 listings available.
• Price trend: Prices have softened 5.23% compared with last year.
• Clean inventory: 74.6% of listings are accident-free.

If you find a listing below $29,120, that's toward the low end of the year-round range and worth acting on quickly.

What is the 2021 Toyota Highlander's resale value?

The current average of $29,169 sits slightly below last year's $30,779.

That softer pricing suggests the Highlander has become a bit more buyer-friendly in the used market. For a future seller, that means you may not see the same pricing strength you would have a year ago, especially if your vehicle has average mileage or visible wear.

Still, the model’s strong reputation, family appeal, and safety focus help support demand. Well-kept examples should remain easier to move than less established competitors, especially if they have clean history and desirable equipment.

Vehicles with strong owner satisfaction ratings, like this model year's 4.9/5, tend to retain buyer demand, which supports resale value over time.

Is the 2021 Toyota Highlander safe?

The 2021 Toyota Highlander earns a five-star overall rating from NHTSA and a Top Safety Pick+ rating from IIHS.

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

Toyota Safety Sense 2.5+ is standard and includes automatic emergency braking with pedestrian detection and intersection support, road-sign assist, adaptive cruise control, lane-departure warning, lane-keeping assist, lane-tracing assist, and automatic high beams. That gives you a broad standard safety package across the lineup.

The main takeaway is that safety is one of the Highlander’s strongest selling points, and Toyota made it even more of a priority for this model year. If safety is high on your list, this is one of the model’s clearest advantages.

Should I buy a 2021 Toyota Highlander 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:

• 37.0% of listings are priced as good or great deals.
• At 74.6% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.
• Price trend: Prices have softened 5.23% compared with last year.
• Owners rate it 4.9/5 — a strong satisfaction signal.
• The 2021 adds standard Toyota Safety Sense 2.5+ with intersection support and other advanced driver aids.

Consider the 2020 if:

• At $27,084, the 2020 costs less than the current year's $29,169 average.
• It emphasizes comfort, a soft ride, and a quiet cabin.

Consider the 2022 if:

• At $31,822, the 2022 costs more than the current year's $29,169 average.
• It keeps the family-focused formula while adding easy-to-use technology and a cramped third row caveat.

The bottom line: The 2021 is the right pick if you want the strongest mix of safety, comfort, and current-market value. If price is your top priority, the 2020 can save you money; if you want a newer-feeling alternative and can spend more, the 2022 is worth a look.

How does the 2021 Toyota Highlander compare to the 2021 Honda Pilot?

Expert Pros & Cons (per CarGurus review team)

2021 Toyota Highlander:

• Pros: Great ride quality, Comfortable, Spacious.
• Cons: Uninspired styling, Underwhelming base engine, Outdated technology.

2021 Honda Pilot:

• Pros: Spacious, Easy-to-use technology, Stylish design.
• Cons: Fairly pedestrian performance, Irritating transmission.

Our experts score the 2021 Toyota Highlander 7.5/10 and the 2021 Honda Pilot 7.2/10. The Highlander has the edge in expert scoring, while the Pilot counters with easier-to-use technology and a more stylish design. The Highlander’s ride quality and comfort stand out, but its base engine and outdated tech are weaker points. The Pilot is also spacious, though its transmission and performance drawbacks keep it slightly behind overall.

Read our full side-by-side expert comparison here.

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