Used 2020 Toyota Highlander for Sale nearChicago, IL

How much does the 2020 Toyota Highlander cost?

Prices have softened 3.89% compared to this time last year, making it a favorable time to shop this model year.

There are 3,469 listings available, which gives you a solid amount of inventory to compare.

Is the 2020 Toyota Highlander a good car?

Yes — the 2020 Toyota Highlander earns a 4.6/5 user rating and a 7.7/10 expert rating. The model scores 9/10 across Form and function and Safety.

Owners consistently praise its smooth ride, advanced features, and spacious interior, and many also highlight its safety features and family-friendly usefulness. The main trade-offs are its poor handling and uninspired styling, and the Highlander is best suited to you if you want a calm, upscale-feeling three-row SUV rather than something sporty. It also fits buyers who value comfort and practicality over driving excitement. With 36.0% of listings marked as good or great deals, the market still offers some attractive opportunities.

Is the 2020 Toyota Highlander reliable?

Owners rate it 4.6/5, a strong signal of long-term satisfaction.

Owners describe it as smooth, dependable, and a vehicle they can count on for family use, with repeated praise for its comfort and features. The expert review also emphasizes its quiet operation and easygoing character, which supports the impression of a well-sorted daily driver. Toyota includes two years of maintenance and roadside assistance.

For used buyers, the main long-term ownership risk is less about outright durability and more about finding one that has been cared for properly, since condition and maintenance history matter a lot on a family SUV.

What should I look for when buying a used 2020 Toyota Highlander?

At 70.2% 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 thorough pre-purchase inspection, especially if the listing price looks unusually strong. Focus on overall condition, signs of prior bodywork, and whether the cabin and exterior wear match the mileage and asking price. Because this model is valued for comfort and family use, you should pay close attention to how well the seats, trim, and controls have held up.

Key things to evaluate:

• Trim level: Every trim except the base L has projector-beam LED headlights and fog lights, while the higher trims add prettier LED running lamps. The Limited and Platinum also get big 20-inch wheels, and the cabin quality and detailing become more upscale as you move up.
• Powertrain: The Highlander uses a 3.5-liter V6 with either front-wheel drive or all-wheel drive. It delivers brisk acceleration, smooth operation, and strong everyday refinement.
• Safety package: Toyota Safety Sense 2.0 is standard, including automatic emergency braking with pedestrian detection and cyclist detection, lane-keeping assist, adaptive cruise control, and automatic high beams. Blind-spot monitoring, parking sensors, and rear emergency braking are optional.
• Infotainment: An 8-inch touchscreen is standard, and Apple CarPlay, Android Auto, and Amazon Alexa integration come standard. Higher trims can get a 12.3-inch touchscreen, plus a 10-inch head-up display and a 7-inch instrument display.
• Fuel efficiency: The Highlander FWD is EPA rated at 21 mpg city, 29 mpg highway, and 24 mpg combined. With AWD, it is 20/27/23.

Which 2020 Toyota Highlander trim should I buy?

The 2020 Toyota Highlander is offered in 5 trim levels: L, LE, XLE, Limited, Platinum.

Here's the short version:

• L: This is the entry point, and it makes sense if you want the Highlander’s comfort, space, and standard safety features at the lowest price.
• LE: This is the best-value trim, because it sits in the low $40,000 range and is called out as the strongest balance of equipment and price.
• XLE: This trim adds more comfort and convenience while staying below the top-end luxury pricing.
• Limited: This is the trim for you if you want the richer cabin, more upscale feel, and the more premium presentation that helps the Highlander feel close to a Lexus.
• Platinum: This is the top choice if you want the most fully equipped Highlander, including the larger screen and the most upscale interior treatment.

Toyota Safety Sense 2.0 is standard across the lineup.

Is now a good time to buy a used 2020 Toyota Highlander?

This looks like a moderate, selective buyer’s market, so you can shop patiently but should move quickly on strong listings.

• Deal availability: 36.0% of listings are priced as good or great deals.
• Inventory: There are 3,469 listings available.
• Price trend: Prices have softened 3.89% compared with last year.
• Clean inventory: 70.2% of listings are accident-free.

If you find a listing below $26,942, that's toward the low end of the year-round range and worth acting on quickly.

What is the 2020 Toyota Highlander's resale value?

The current average of $27,363 sits slightly below last year's $28,470.

That price movement suggests the market has already adjusted downward, which can help you buy at a more favorable entry point today. For a future seller, the softer trend means resale gains may be harder to realize unless the vehicle is especially clean, well maintained, and attractively equipped. Strong condition and a good history report should matter more than ever if you want to protect value.

Vehicles with strong owner satisfaction ratings, like this model year's 4.6/5, tend to retain buyer demand, which supports resale value over time.

Is the 2020 Toyota Highlander safe?

The 2020 Highlander earns a 2020 Top Safety Pick from the IIHS.

It earns a 9/10 safety score from our experts.

Toyota Safety Sense 2.0 is standard, and it includes automatic emergency braking with pedestrian detection and cyclist detection, lane-keeping assist, adaptive cruise control, and automatic high beams. Blind-spot monitoring, parking sensors, and rear emergency braking are optional, so you should check whether a used example has the extra driver-assistance equipment you want.

Should I buy a 2020 Toyota Highlander or consider a different year?

If you're weighing the 2020 against nearby model years, here's how to think about it:

Choose the 2020 if:

• 36.0% of listings are priced as good or great deals.
• At 70.2% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.
• Price trend: Prices have softened 3.89% compared with last year.
• Owners rate it 4.6/5 — a strong satisfaction signal.
• The 2020 redesign emphasizes comfort, quietness, and a more premium feel.

Consider the 2021 if:

• At $29,403, the 2021 costs more than the current year's $27,363 average.
• It adds more standard safety-feature technology.

The bottom line: If you want the better value today, the 2020 is the smarter buy because it combines a lower average price with strong owner satisfaction and a comfortable, upscale driving experience. If you are willing to pay more for additional standard safety technology, the 2021 is the cleaner upgrade path.

How does the 2020 Toyota Highlander compare to the 2020 Honda Pilot?

Expert Pros & Cons (per CarGurus review team)

2020 Toyota Highlander:

• Pros: Standard advanced safety features, Spacious.
• Cons: Poor handling, Uninspired styling.

2020 Honda Pilot:

• Pros: Powerful engine, Standard advanced safety features.
• Cons: Unintuitive technology, Interior materials feel cheap.

Our experts score the 2020 Toyota Highlander 7.7/10 and the 2020 Honda Pilot 8/10. The Highlander leans harder into comfort and a more premium-feeling cabin, while the Pilot gets the edge for power. If you care most about a relaxed ride and upscale feel, the Highlander is the better fit; if you want stronger engine performance, the Pilot has the advantage. Both bring standard advanced safety features, but each has its own compromises.

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

These recommendations are based on CarGurus' proprietary market data from October 27, 2026, CarGurus experts' opinions, and generative AI.