Used 2020 Toyota Highlander for Sale near Chicago, IL
221 results
CarGurus Analysis:
2020 Toyota Highlander
With 214 currently listed for sale near Chicago, IL and an average price of $28,452.00, 32.2% of 2020 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
Favorably reviewed: Owners rated the 2020 Toyota Highlander 4.6 / 5 stars.
92.5% of 2020 Highlander models on CarGurus are accident free.
The 2020 Toyota Highlander stands out for its spacious interior, smooth ride, and robust safety features, making it a preferred choice for families.
CarGurus Analysis: 2020 Toyota Highlander
overall
Summary
With 214 currently listed for sale near Chicago, IL and an average price of $28,452.00, 32.2% of 2020 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
Favorably reviewed: Owners rated the 2020 Toyota Highlander 4.6 / 5 stars.
92.5% of 2020 Highlander models on CarGurus are accident free.
The 2020 Toyota Highlander stands out for its spacious interior, smooth ride, and robust safety features, making it a preferred choice for families.
Why it stands out
The 2020 Toyota Highlander is designed to deliver family-friendly space, comfort, and safety, distinguishing itself in the competitive midsize SUV market. Redesigned for 2020, the Highlander offers a quiet and cushioned ride, with an interior that rivals luxury vehicles, particularly in the upper trim levels. The advanced safety features, part of the Toyota Safety Sense 2.0 package, include automatic emergency braking and lane-keeping assist, essential for today’s safety-conscious drivers. While its performance may not be as thrilling—often criticized for less responsive handling—the Highlander fulfills most family needs effortlessly, making it an ideal choice for those prioritizing comfort and peace of mind during their travels.
Other model years to consider
- Average price: $35,827.00
- Good/great deal percentage: 49.8%
- User rating: 5 / 5
- Total listings: 203
- Average price: $36,640.00
- Good/great deal percentage: 48.8%
- User rating: 4.75 / 5
- Total listings: 260
- Average price: $29,851.00
- Good/great deal percentage: 41.0%
- User rating: 4.86 / 5
- Total listings: 217
This analysis is based on CarGurus' proprietary market data from June 2, 2026, CarGurus experts' opinions, and generative AI.
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4.6 Overall rating
Filter by rating
Sarah T
Reviewed a 2020 Toyota Highlander on Dec 7, 2025
It’s well-equipped, comfortable, and family-friendly SUV with strong safety tech, a smooth ride, and premium touches (thanks to the platinum trim) like a panoramic moonroof, leather seating, and 12” touchscreen. Its V6 offers solid power and decent fuel efficiency for a 3-row SUV, and overall it feels modern, quiet, and refined. It’s a great value if you want a reliable, upscale daily driver! The main thing it’s missing is more usable third-row and cargo space. The 3rd row is tight for adults and cargo behind it is limited. Otherwise, it’s a strong all-around pick and fits exactly what I was looking for. I would compare this to the Kia Telluride, Hyundai Palisade, Honda Pilot, and the Ford Explorer.
Anonymous
Reviewed a 2020 Toyota Highlander on Nov 8, 2020
Most comfortable riding vehicle that we have ever purchased. Great features and a great looking vehicle as well.
Kris B
Reviewed a 2020 Toyota Highlander on May 22, 2023
Absolutely love this car. Great comfortable family vehicle with plenty of space, and features
Lee W
Reviewed a 2020 Toyota Highlander on Feb 28, 2020
The ride was smooth, the Highlander is quick and very quiet. I loved many of the features it had, like the posted speed limit on the instrument cluster. What really disappointed me was the passenger seat comfort. The seat bottom only adjusts fron-to-rear, not up or down so I wasn’t as comfortable in it as I was the Hyundai Palisade or the Kia Telluride. It’s still a really good vehicle.
2020 Toyota Highlander Trims
| Trim type | MSRP |
|---|---|
| L AWD | $36,200 |
| LE FWD | $36,800 |
| LE AWD | $38,400 |
| Limited FWD | $43,650 |
| Limited AWD | $45,600 |
| Platinum AWD | $48,800 |
| XLE FWD | $39,600 |
| XLE AWD | $41,200 |
2020 Toyota Highlander Price Trends
CarGurus tracks the prices of millions of used car listings every year. See how the average price of 2020 Toyota Highlander prices has changed over time.
See more price trends2020 Toyota Highlander Pricing Analysis: Chicago, IL Market Report
Pricing by Nearby Locations
Market Area: Chicago, IL
Key Insights
- Highest Prices in Janesville, WI: This market leads with an average price of $33,425, likely due to limited availability.
- Best Deals in Palatine, IL: With an average price of $28,976, it offers significant savings compared to other nearby locations.
- Overall Inventory Range: Cities like Aurora, IL (222 listings) and Kenosha, WI (202 listings) show a healthy inventory, suggesting responsive demand in the market.
City-Level Pricing
| City | Total Listings | Avg Price |
|---|---|---|
| Janesville, WI | 163 | $33,425 |
| Rockford, IL | 172 | $31,070 |
| South Bend, IN | 171 | $29,476 |
| Palatine, IL | 214 | $28,976 |
| Aurora, IL | 222 | $28,312 |
| Kenosha, WI | 202 | $28,226 |
| Milwaukee, WI | 166 | $28,481 |
| Holland, MI | 186 | $30,438 |
| Kalamazoo, MI | 183 | $30,443 |
| Lafayette, IN | 191 | $27,811 |
Pricing by Trim Packages
Key Insights
- XLE AWD Most Common: The XLE AWD trim is the leading option with 240 listings, reflecting consumer preference for all-wheel drive.
- Price Variation Across Trims: The Limited AWD trim’s MSRP of $45,600 indicates a ~10% premium over the XLE AWD, suggesting value in additional features.
- An Abundance of AWD Options: All trims, particularly AWD versions, dominate listings, catering to demand for enhanced traction in varying climates.
Trim-Level Details
| Trim | Listings | MSRP | Drivetrain | Engine |
|---|---|---|---|---|
| XLE AWD | 240 | $41,200 | AWD | 3.5L 295 hp V6 |
| Limited AWD | 104 | $45,600 | AWD | 3.5L 295 hp V6 |
| XLE FWD | 52 | $39,600 | FWD | 3.5L 295 hp V6 |
| LE AWD | 70 | $38,400 | AWD | 3.5L 295 hp V6 |
| LE FWD | 37 | $36,800 | FWD | 3.5L 295 hp V6 |
| Platinum AWD | 47 | $48,800 | AWD | 3.5L 295 hp V6 |
| Limited FWD | 25 | $43,650 | FWD | 3.5L 295 hp V6 |
| Limited Platinum AWD | 23 | $48,800 | AWD | 3.5L 295 hp V6 |
Pricing Analysis by Model Year
Key Insights
- New Models Attract a Premium: The 2026 Highlander is valued at $51,882, representing a 13.3% markup over its starting MSRP, indicating strong demand.
- Depreciation Rate Increases for Older Models: The 2019 Highlander has seen a ~20.2% decline in value compared to its original MSRP, illustrating the typical depreciation trend.
- 2021 Model Represents Best Value: The 2021 Highlander averages $29,916, showing modest depreciation of ~14.3% from its original price, making it an attractive option for budget-conscious buyers.
Model Year Pricing
| Model Year | Original MSRP | Avg Price | Price vs MSRP |
|---|---|---|---|
| 2026 Toyota Highlander | $45,870 | $51,882 | +13.3% |
| 2025 Toyota Highlander | $40,320 | $41,202 | +2.2% |
| 2024 Toyota Highlander | $39,270 | $37,088 | -5.5% |
| 2023 Toyota Highlander | $36,620 | $36,348 | -0.7% |
| 2022 Toyota Highlander | $35,855 | $34,735 | -3.1% |
| 2021 Toyota Highlander | $35,085 | $29,916 | -14.3% |
| 2019 Toyota Highlander | $31,830 | $25,407 | -20.2% |
| 2018 Toyota Highlander | $31,230 | $23,030 | -26.4% |
| 2017 Toyota Highlander | $30,630 | $20,186 | -34.1% |
| 2016 Toyota Highlander | $30,490 | $19,546 | -35.9% |
| 2015 Toyota Highlander | $29,765 | $17,112 | -42.5% |
These recommendations are based on CarGurus' proprietary market data from June 4, 2026, CarGurus experts' opinions, and generative AI.
