Used 2021 Toyota Highlander for Sale nearChicago, IL

How much does the 2021 Toyota Highlander cost?

Prices have softened 5.86% compared to this time last year, making it a favorable time to shop this model year.

There are 3,365 listings available, which gives you a solid pool of inventory to compare.

Is the 2021 Toyota Highlander a good car?

Yes — the 4.86/5 user rating points to strong owner satisfaction, and the expert rating is 7.5/10. The standout strength is Safety at 10/10.

Owners consistently praise its comfort, reliability, and features, along with the smooth ride and high-quality interior. Spaciousness and safety features also come up often, which fits a family-focused three-row SUV.

The trade-offs are familiar: the base engine is underwhelming, the styling is uninspired, and the technology feels dated. Even so, if you want a roomy, comfortable SUV with a straightforward family-hauling mission, the Highlander lines up well with that use case.

Good and great deals account for 36.2% of listings, so you still have room to shop selectively.

Is the 2021 Toyota Highlander reliable?

Owners rate it 4.86/5, a strong signal of long-term satisfaction. The user feedback also emphasizes reliability, and the expert evaluation points to smooth, predictable operation and a reputation for reliability.

That dependability theme matters if you want a used three-row SUV you can count on for daily family duty. Toyota also positions the Highlander as a practical, comfort-first choice, which supports the case for long-term ownership.

The main used-buyer risk is that higher-mileage examples may show the usual wear associated with a busy family hauler, so condition and maintenance history matter.

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

Accident-free inventory is solid at 76.3% — always verify the vehicle history report.

You should still check the history report carefully, because accident-free status is only one part of the picture. Prioritize a thorough inspection of the cabin, electronics, and suspension, since this model is meant to serve as a daily family vehicle. Focus on overall condition, especially if you’re comparing higher-mileage examples or trims with more equipment.

Key things to evaluate:

• Trim level: The XSE adds a more aggressive front end, 20-inch wheels with black accents, a unique front fascia, a lower spoiler, and a bit of suspension tuning, while the Limited trim brings a more upscale look and a richer interior feel. The base trims miss some of the more premium presentation and equipment, so you should decide whether you want style, comfort, or value.
• Powertrain: Every Highlander uses a 3.5-liter V6 with 295 horsepower and 263 pound-feet of torque, paired with an eight-speed automatic transmission and front-wheel drive or all-wheel drive. It is smooth and predictable rather than quick, and the XSE adds firmer suspension tuning for a slightly more engaging feel.
• 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 use an 8-inch touchscreen, while the Limited can get a 12.3-inch screen and the Platinum makes it standard. Android Auto and Apple CarPlay are standard, and the larger screen is bright and crisp.
• Fuel efficiency: The V6 returns 21 mpg city, 29 highway, and 24 combined with front-wheel drive, or 20/27/23 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, safety, and V6 power without stretching your budget. It gives you the essentials, but you give up the more upscale cabin feel and larger-screen tech found higher up.
• XLE: This is the trim that most shoppers should cross-shop first because it adds more everyday comfort and convenience without jumping all the way to luxury pricing. It’s the best-value choice if you want a well-rounded family SUV.
• XSE: This trim adds the sportier appearance package, 20-inch wheels, and suspension tuning for shoppers who want a little more attitude. It is more about style and feel than outright performance.
• Limited: This is the trim where the Highlander starts to feel genuinely upscale, with chrome accents, a more premium interior, and the option for the larger 12.3-inch touchscreen. If you want the most polished balance of comfort and features, this is the sweet spot.
• Platinum: This is the top-tier choice if you want the biggest screen and the most premium presentation. It makes the Highlander feel the most fully equipped, but you pay for that upgrade.
• Limited trim: This trim sits just below Platinum in the hierarchy and is described as especially upscale inside, with near-flawless fit and finish and a more luxurious cabin feel.

Toyota Safety Sense 2.5+ is standard across the lineup, so you do not need to move up a trim just to get the core safety suite.

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

This is a moderate market for selective buyers, so you can shop with some leverage if you stay patient.

• Deal availability: 36.2% of listings are priced as good or great deals.
• Inventory: There are 3,365 listings available.
• Price trend: Prices have softened 5.86% compared with last year.
• Clean inventory: 76.3% of listings are accident-free.

If you find a listing below $29,156, 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 $29,775 sits slightly below last year's $31,628.

That softer pricing suggests the market has cooled a bit, which can help you as a buyer today but may temper what a future seller can ask. If you buy at the right price and keep the vehicle in strong condition, you can still protect value reasonably well.

The Highlander’s broad appeal, strong owner satisfaction, and family-friendly reputation should help support demand over time. Still, resale will depend heavily on mileage, condition, and how well the vehicle has been maintained.

Vehicles with strong owner satisfaction ratings, like this model year's 4.86/5, 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 it 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 set of driver-assistance features without needing to climb the trim ladder.

The safety story is especially strong for used buyers because the core suite is standard across the lineup. That means you can shop for value without giving up the Highlander’s main safety advantage.

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:

• 36.2% of listings are priced as good or great deals.
• Accident-free inventory is solid at 76.3% — always verify the vehicle history report.
• Price trend: Prices have softened 5.86% compared with last year.
• Owners rate it 4.86/5 — a strong satisfaction signal.
• Toyota adds Toyota Safety Sense 2.5+ as standard equipment this year.

Consider the 2020 if:

• At $27,527, the 2020 costs less than the current year's $29,775 average.
• It emphasizes comfort, quiet operation, and a Lexus-like feel.

Consider the 2022 if:

• At $32,217, the 2022 costs more than the current year's $29,775 average.
• It adds more versatility and easy-to-use tech for family buyers.

The bottom line: If you want the best mix of price, safety, and family-friendly comfort, the 2021 is the one to target. If your budget is tighter, the 2020 can save you money while keeping the Highlander’s core strengths intact. If you want to spend more for a newer-feeling package, the 2022 is worth a look, but the 2021 remains the smarter middle ground for most used buyers.

These recommendations are based on CarGurus' proprietary market data from September 29, 2026, CarGurus experts' opinions, and generative AI.