Used 2023 Toyota Highlander for Sale near Chicago, IL
269 results
CarGurus Analysis:
2023 Toyota Highlander
With 270 currently listed for sale near Chicago, IL and an average price of $35,729.00, 50.4% of 2023 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
Favorably reviewed: Owners rated the 2023 Toyota Highlander 4.75 / 5 stars.
100.0% of 2023 Highlander models on CarGurus are accident free.
CarGurus Analysis: 2023 Toyota Highlander
Summary
With 270 currently listed for sale near Chicago, IL and an average price of $35,729.00, 50.4% of 2023 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
Favorably reviewed: Owners rated the 2023 Toyota Highlander 4.75 / 5 stars.
100.0% of 2023 Highlander models on CarGurus are accident free.
Why it stands out
The 2023 Toyota Highlander continues the legacy of its predecessors by merging comfort, reliability, and safety in a spacious midsize SUV package. Known for its smooth ride and practicality, the Highlander stands out with its availability of hybrid models, enhancing fuel efficiency without compromising performance. The recent addition of a turbocharged four-cylinder engine boasts improved power and competitive fuel economy, which appeals to buyers looking for a versatile family vehicle. Its generous standard safety features backed by Toyota Safety Sense ensure peace of mind for families on the move. While the Highlander excels in reliability and comfort, it may lack some excitement in the driving dynamics, making it more of a reliable tool than a thrilling ride. Overall, it remains a top pick for those seeking a dependable and spacious SUV.
Other model years to consider
- Average price: $37,140.00
- Good/great deal percentage: 52.8%
- User rating: 5 / 5
- Total listings: 214
- Average price: $30,052.00
- Good/great deal percentage: 39.9%
- User rating: 4.86 / 5
- Total listings: 223
- Average price: $34,972.00
- Good/great deal percentage: 43.7%
- User rating: 4.44 / 5
- Total listings: 300
This analysis is based on CarGurus' proprietary market data from June 9, 2026, CarGurus experts' opinions, and generative AI.
Relevant articles
Toyota Highlander Buying Guide: Cost, Reliability, and the Best Years to Buy
Discover the ultimate buying guide for purchasing a used Toyota Highlander, covering every generation since 2001. Whether you're a first-time buyer or a Toyota loyalist, this comprehensive overview will help you research your next pre-owned Toyota Highlander.
The Best Three-Row SUVs of 2026
There’s no escaping it: SUVs are everywhere. Minivans offer the space for the most passengers and gear, but big, three-row SUVs deliver on both while offering some level of performance, on and off the paved roads.
The Best Used SUVs Under $10,000 in 2026
Can you get a great SUV for less than $10,000? Heck, yes! Our guide runs through the top 10, with options including family favorites and some upscale options.
4.8 Overall rating
Filter by rating
Jennifer M
Reviewed a 2023 Toyota Highlander on Apr 21, 2026
Great value. This car had everything you could want without buying the fanciest top of the line model.
Samuel B
Reviewed a 2023 Toyota Highlander on Oct 20, 2023
Extremely smooth ride and very comfortable seats. Love the interior layout.
Alexander H
Reviewed a 2023 Toyota XSE AWD on Aug 11, 2023
New 4cyl. is peppy enough, just seems out of place in a vehicle this size. That plus the buzzing of something so small compared to the V6 leaves much to be desired. Handling is great. With the xse sport tuned suspension...it drives relatively good. Only upside of going for the premium audio is the 12.3 inch infotainment. The jbl premium sound doesnt do it for me. Shallow sound and lackluster bass. Build quality is what youd expect from Toyota, surprising actually...in a good way. Seats are comfortable for those lucky to be in the 2 front rows. The third should be reserved for small children or average sized adults in a pinch. Cargo space is a bit small but its what to expect in this segment. The third row means some compromise in that dept. Overall, I love my new Highlander. Its definitely not without flaws but they are easy to look past.
Xexeed M
Reviewed a 2023 Toyota Highlander on May 4, 2023
Car’s 3rd row is not bumpy. Features like Birds Eye view are fantastic. Drives very smooth.
2023 Toyota Highlander Trims
| Trim type | MSRP |
|---|---|
| Platinum AWD | $51,425 |
| Limited AWD | $48,225 |
| LE AWD | $40,620 |
| L FWD | $36,620 |
| XSE AWD | $45,565 |
| LE FWD | $39,020 |
| XLE FWD | $42,020 |
| XLE AWD | $43,620 |
2023 Toyota Highlander Price Trends
CarGurus tracks the prices of millions of used car listings every year. See how the average price of 2023 Toyota Highlander prices has changed over time.
See more price trends2023 Toyota Highlander Pricing Analysis: Chicago, IL Market Report
Pricing by Nearby Locations
Market Area: Chicago, IL
Key Insights
- Highest Price in Janesville: The highest average price is found in Janesville, WI at $38,245, indicating potentially limited inventory.
- Lowest Priced Option in Palatine: Palatine, IL offers the best price at $35,988, reflecting a more competitive market or higher inventory.
- Pricing Consistency Across Cities: The average prices across these markets vary slightly but generally remain in the range of $35,000 to $39,000.
City-Level Pricing
| City | Total Listings | Avg Price |
|---|---|---|
| Janesville, WI | 158 | $38,245 |
| South Bend, IN | 163 | $36,940 |
| Milwaukee, WI | 161 | $36,738 |
| Kenosha, WI | 232 | $36,238 |
| Rockford, IL | 175 | $35,327 |
| Aurora, IL | 249 | $35,878 |
| Palatine, IL | 244 | $35,988 |
| Holland, MI | 158 | $35,437 |
| Kalamazoo, MI | 163 | $35,648 |
| Lafayette, IN | 203 | $39,217 |
Pricing by Trim Packages
Key Insights
- XLE AWD is the Most Available Trim: With 241 listings, it represents a significant portion of the market, likely aligning with consumer preference for AWD vehicles.
- Limited AWD Provides Premium Features: The Limited AWD trim priced at $48,225 offers a considerable upgrade with premium features and positions as a high-value option for consumers seeking luxury.
- Price Range Reflects Feature Set: The variance of $21,100 between the base LE AWD ($40,620) and the high-end Platinum AWD ($51,425) illustrates the breadth of offerings tailored to different buyer needs.
Trim-Level Details
| Trim | Listings | MSRP | Drivetrain | Engine |
|---|---|---|---|---|
| XLE AWD | 241 | $43,620 | AWD | 2.4L 265 hp I4 |
| Limited AWD | 104 | $48,225 | AWD | 2.4L 265 hp I4 |
| LE AWD | 69 | $40,620 | AWD | 2.4L 265 hp I4 |
| Platinum AWD | 47 | $51,425 | AWD | 2.4L 265 hp I4 |
| XLE FWD | 52 | $42,020 | FWD | 2.4L 265 hp I4 |
| LE FWD | 37 | $39,020 | FWD | 2.4L 265 hp I4 |
| XSE AWD | 34 | $45,565 | AWD | 2.4L 265 hp I4 |
| Limited FWD | 25 | $46,275 | FWD | 2.4L 265 hp I4 |
Pricing Analysis by Model Year
Key Insights
- Newer Models Retain Higher Value: The 2026 model has a current average price of $51,882, reflecting a strong demand despite being above the original MSRP of $45,870 (+13.9%).
- Depreciation Trend is Apparent: Vehicles from 2021 and older show significant depreciation, with 2019 models down about 20.2% from their MSRP.
- Best Value in Recent Models: The 2024 Highlander drops below MSRP by 5.0%, suggesting it may be a sweet spot for shoppers looking for nearly new at a good price.
Model Year Pricing
| Model Year | Original MSRP | Avg Price | Price vs MSRP |
|---|---|---|---|
| 2026 Toyota Highlander | $45,870 | $51,882 | +13.9% |
| 2025 Toyota Highlander | $40,320 | $41,202 | +2.2% |
| 2024 Toyota Highlander | $39,270 | $37,088 | -5.6% |
| 2022 Toyota Highlander | $35,855 | $34,735 | -3.1% |
| 2021 Toyota Highlander | $35,085 | $29,916 | -14.5% |
| 2020 Toyota Highlander | $34,600 | $28,312 | -18.1% |
| 2019 Toyota Highlander | $31,830 | $25,407 | -20.2% |
| 2018 Toyota Highlander | $31,230 | $23,030 | -26.3% |
| 2017 Toyota Highlander | $30,630 | $20,186 | -34.3% |
| 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.
