New & Used 2026 Toyota Highlander for Sale nearChicago, IL
Shop with transparent pricing.
Only show listings that include dealer fees- Year:
- 2025
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Blueprint
- Fuel type:
- Gasoline
- Transmission:
- 8-Speed Automatic
- Mileage:
- 24,069
- Stock #:
- 12968P
- VIN:
- 5TDKDRAH8SS555672


Sponsored by McGrath Elmhurst Toyota
2025 Toyota Highlander
XLE FWD
24,069 mi
$41,366
- Year:
- 2025
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- White (Wind Chill Pearl)
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Transmission:
- 8-Speed Automatic
- Mileage:
- 12,025
- Stock #:
- TR43648
- VIN:
- 5TDKDRBH3SS589680

Sponsored Listing
2025 Toyota Highlander
XLE AWD
12,025 mi
$47,278
- Year:
- 2025
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Red (Ruby Flare Pearl)
- Fuel type:
- Gasoline
- Interior color:
- Gray (Graphite)
- Transmission:
- Automatic
- Mileage:
- 23,685
- Stock #:
- P12080
- VIN:
- 5TDKDRAH4SS555541

Sponsored Listing
2025 Toyota Highlander
XLE FWD
23,685 mi
$43,337
- Year:
- 2025
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Celestial Silver Metallic
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 24,931
- Stock #:
- P7352
- VIN:
- 5TDKDRBH5SS583265

2025 Toyota Highlander
XSE AWD
24,931 mi
$42,010
- Year:
- 2026
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Black
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 8,056
- Stock #:
- TS601793
- VIN:
- 5TDKDRBHXTS601793

2026 Toyota Highlander
XLE AWD
8,056 mi
$44,254
- Year:
- 2025
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Silver
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 20,885
- Stock #:
- SS588777
- VIN:
- 5TDKDRBH2SS588777

2025 Toyota Highlander
XSE AWD
20,885 mi
$43,498
- Year:
- 2025
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Magnetic Gray Metallic
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 19,572
- Stock #:
- 577767
- VIN:
- 5TDKDRBHXSS577767

-$1,000
2025 Toyota Highlander
XSE AWD
19,572 mi
$45,039
$44,039
- Year:
- 2025
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Magnetic Gray Metallic
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 18,171
- Stock #:
- 92F07603
- VIN:
- 5TDKDRBH6SS586062

2025 Toyota Highlander
XLE AWD
18,171 mi
$44,238
- Year:
- 2025
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Heavy Metal
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 36,997
- Stock #:
- T13961
- VIN:
- 5TDKDRBH1SS576281

2025 Toyota Highlander
XLE AWD
36,997 mi
$40,593
- Year:
- 2025
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- White (Wind Chill Pearl)
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 34,521
- Stock #:
- T13679
- VIN:
- 5TDKDRBH1SS577964

2025 Toyota Highlander
LE AWD
34,521 mi
$35,743
- Year:
- 2025
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 30,476
- Stock #:
- B7G586511
- VIN:
- 5TDKDRBH9SS586511

2025 Toyota Highlander
XLE AWD
30,476 mi
$43,875
- Year:
- 2025
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Gray
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 31,873
- Stock #:
- 62040
- VIN:
- 5TDKDRAH7SS554089

2025 Toyota Highlander
LE FWD
31,873 mi
$35,373
- Year:
- 2025
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Magnetic Gray Metallic
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 33,609
- Stock #:
- N260354A
- VIN:
- 5TDKDRBH9SS577923

2025 Toyota Highlander
XLE AWD
33,609 mi
$43,879
CarGurus Analysis:
2026 Toyota Highlander
With 37 currently listed for sale near Chicago, IL and an average price of $45,000.00, 45.9% of 2026 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
100.0% of 2026 Highlander models on CarGurus are accident free.
The 2026 Toyota Highlander continues to impress with its spacious interior, excellent safety ratings, and the availability of hybrid models, making it a practical choice for families.
- Year:
- 2025
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 37,662
- Stock #:
- B7V576342
- VIN:
- 5TDKDRBH6SS576342

2025 Toyota Highlander
XLE AWD
37,662 mi
$43,244
- Year:
- 2025
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Midnight Black Metallic
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray (Graphite)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 21,098
- Stock #:
- 26712AT
- VIN:
- 5TDKDRBH5SS594136

2025 Toyota Highlander
Platinum AWD
21,098 mi
$52,894
- Year:
- 2025
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Heavy Metal
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 48,883
- Stock #:
- AH552334
- VIN:
- 5TDKDRAH6SS552334

2025 Toyota Highlander
XLE FWD
48,883 mi
$37,909
- Year:
- 2025
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Red (Ruby Flare Pearl)
- Fuel type:
- Gasoline
- Interior color:
- Gray (Graphite)
- Transmission:
- Automatic
- Mileage:
- 23,685
- Stock #:
- P12080
- VIN:
- 5TDKDRAH4SS555541

2025 Toyota Highlander
XLE FWD
23,685 mi
$43,337
- Year:
- 2025
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Celestial Silver Metallic
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 34,946
- Stock #:
- T13887
- VIN:
- 5TDKDRBH8SS576455

2025 Toyota Highlander
XLE AWD
34,946 mi
$40,743
- Year:
- 2025
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Blueprint
- Fuel type:
- Gasoline
- Transmission:
- 8-Speed Automatic
- Mileage:
- 24,069
- Stock #:
- 12968P
- VIN:
- 5TDKDRAH8SS555672

2025 Toyota Highlander
XLE FWD
24,069 mi
$41,366
- Year:
- 2025
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Black
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 26,011
- Stock #:
- 62028
- VIN:
- 5TDKDRAH1SS553889

2025 Toyota Highlander
LE FWD
26,011 mi
$35,995
- Year:
- 2025
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- White (Wind Chill Pearl)
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Transmission:
- 8-Speed Automatic
- Mileage:
- 37,357
- Stock #:
- 13042P
- VIN:
- 5TDKDRBH2SS588794

2025 Toyota Highlander
LE AWD
37,357 mi
$39,987
- Year:
- 2025
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Magnetic Gray Metallic
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 23,576
- Stock #:
- OP34515
- VIN:
- 5TDKDRBH5SS587428

2025 Toyota Highlander
XSE AWD
23,576 mi
$42,624
- Year:
- 2025
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Silver
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 20,885
- Stock #:
- SS588777
- VIN:
- 5TDKDRBH2SS588777

Sponsored Listing
2025 Toyota Highlander
XSE AWD
20,885 mi
$43,498
CarGurus Analysis: 2026 Toyota Highlander

Summary
With 37 currently listed for sale near Chicago, IL and an average price of $45,000.00, 45.9% of 2026 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
100.0% of 2026 Highlander models on CarGurus are accident free.
The 2026 Toyota Highlander continues to impress with its spacious interior, excellent safety ratings, and the availability of hybrid models, making it a practical choice for families.
Why it stands out
The 2026 Toyota Highlander stands out in the crowded midsize SUV market due to its blend of reliability, spaciousness, and safety features. With a history of strong performance and a reputation for durability, the Highlander appeals to families looking for a vehicle that can accommodate both passengers and cargo comfortably. The latest model maintains its commitment to safety, boasting a 100% accident-free rate among listings. Additionally, the Highlander offers hybrid options, enhancing fuel efficiency without sacrificing power. While it may not be the most thrilling drive, its smooth ride and practical features make it a solid choice for everyday use.
Other model years to consider
- Average price: $43,000.00
- Good/great deal percentage: 43.2%
- User rating: 4.75 / 5
- Total listings: 257
- Average price: $39,000.00
- Good/great deal percentage: 34.4%
- User rating: 4.86 / 5
- Total listings: 241
- Average price: $30,000.00
- Good/great deal percentage: 29.2%
- User rating: 4.93 / 5
- Total listings: 154
This analysis is based on CarGurus' proprietary market data from July 21, 2026, CarGurus experts' opinions, and generative AI.
2026 Toyota Highlander Trims
| Trim type | MSRP |
|---|---|
| Platinum AWD | $53,925 |
| XLE AWD | $46,270 |
| XSE AWD | $48,340 |
| Limited AWD | $50,725 |
2026 Toyota Highlander Price Trends
CarGurus tracks the prices of millions of used car listings every year. See how the average price of 2026 Toyota Highlander prices has changed over time.
See more price trends2026 Toyota Highlander Pricing Analysis: Chicago, IL Market Report
Pricing by Nearby Locations
Market Area: Chicago, IL
Key Insights
- Highest Prices in Milwaukee: The market in Milwaukee, WI ($49,394) shows the highest average price, likely due to demand for larger family vehicles in urban areas.
- Lowest Prices in Rockford: Rockford, IL ($43,899) offers the lowest average price among nearby cities, indicating a more price-sensitive market or higher inventory turnover.
- Consistent Pricing Across Suburbs: Cities like Palatine, Aurora, and Janesville all average $43,899, suggesting stable pricing dynamics in suburban areas.
City-Level Pricing
| City | Total Listings | Avg Price |
|---|---|---|
| Milwaukee, WI | 38 | $49,394 |
| Kenosha, WI | 50 | $46,647 |
| Palatine, IL | 42 | $43,899 |
| Aurora, IL | 42 | $43,899 |
| Rockford, IL | 27 | $43,899 |
| Janesville, WI | 31 | $43,899 |
Pricing by Trim Packages
Key Insights
- XLE AWD is the Most Common Trim: With 254 listings, the XLE AWD trim is the most prevalent, indicating strong demand for its features and pricing.
- Premium Pricing for Limited AWD: The Limited AWD trim, priced at $50,725 MSRP, reflects a significant markup due to its luxury features, appealing to buyers seeking higher-end options.
- Consistent Drivetrain Across Trims: All trims listed feature the same 2.4L 265 hp I4 engine and AWD, catering to a market that values all-weather capability.
Trim-Level Details
| Trim | Listings | MSRP | Drivetrain | Engine |
|---|---|---|---|---|
| XLE AWD | 254 | $46,270 | AWD | 2.4L 265 hp I4 |
| Limited AWD | 117 | $50,725 | AWD | 2.4L 265 hp I4 |
| XSE AWD | 55 | $48,340 | AWD | 2.4L 265 hp I4 |
| Platinum AWD | 49 | $53,925 | AWD | 2.4L 265 hp I4 |
Pricing Analysis by Model Year
Key Insights
- Newer Models Retain Value: The 2025 Highlander is priced at $39,702, which is approximately −1.5% below MSRP, indicating strong demand for the latest model.
- Significant Depreciation for Older Models: The 2019 Highlander shows a steep decline, with an average price of $25,154, reflecting a −21.1% depreciation from its original MSRP.
- Best Value in Recent Years: The 2022 Highlander is priced at $35,041, only −2.3% below MSRP, making it a compelling option for buyers looking for a balance of price and features.
Model Year Pricing
| Model Year | Original MSRP | Avg Price | Price vs MSRP |
|---|---|---|---|
| 2025 Toyota Highlander | $40,320 | $39,702 | -1.5% |
| 2024 Toyota Highlander | $39,270 | $37,119 | -5.5% |
| 2023 Toyota Highlander | $36,620 | $34,934 | -4.6% |
| 2022 Toyota Highlander | $35,855 | $35,041 | -2.3% |
| 2021 Toyota Highlander | $35,085 | $30,075 | -14.3% |
| 2020 Toyota Highlander | $34,600 | $25,656 | -25.9% |
| 2019 Toyota Highlander | $31,830 | $25,154 | -21.1% |
| 2018 Toyota Highlander | $31,230 | $22,588 | -27.7% |
| 2017 Toyota Highlander | $30,630 | $20,128 | -34.2% |
| 2016 Toyota Highlander | $30,490 | $19,690 | -35.5% |
| 2015 Toyota Highlander | $29,765 | $18,507 | -37.8% |
These recommendations are based on CarGurus' proprietary market data from July 23, 2026, CarGurus experts' opinions, and generative AI.
Is the 2026 Toyota Highlander a good car?
The 2026 Toyota Highlander stands out in the crowded midsize SUV market because it blends reliability, comfort, and safety. It offers a spacious interior that can accommodate up to seven passengers, which makes it a practical fit for families. It also has a refined ride quality and advanced safety technologies, so you get a vehicle that prioritizes everyday ease and peace of mind over excitement.
That makes it a strong choice if you want a family-friendly SUV that focuses on practicality, comfort, and efficiency rather than sporty driving dynamics. Market availability is moderate, with 32.4% of listings marked as good or great deals.
Is the 2026 Toyota Highlander reliable?
The 2026 Toyota Highlander has a strong reputation for reliability, and it also benefits from a blend of comfort and safety that supports confident daily use. Its fuel efficiency, especially in hybrid variants, adds to its appeal if you want a practical SUV that can handle family duty without demanding much from you.
For used buyers, the main long-term ownership risk is less about the model’s core reputation and more about how well a specific example was maintained and driven.
What should I look for when buying a used 2026 Toyota Highlander?
Accident-free inventory is excellent at 94.5% — clean inventory, standard diligence applies.
You should still run a history report on any listing you’re seriously considering, even when the market looks clean. Prioritize a pre-purchase inspection that focuses on overall condition, signs of prior damage, and how well the vehicle has been maintained. Since this model is often chosen for family use, pay close attention to interior wear, tire condition, and evidence of heavy daily use.
Is now a good time to buy a used 2026 Toyota Highlander?
This looks like a moderate, selective buyer’s market, so you have room to shop carefully without expecting every listing to be a standout deal.
- Deal availability: 32.4% of listings are priced as good or great deals.
- Inventory: There are 831 listings available.
- Clean inventory: 94.5% of listings are accident-free.
If you find a listing below $49,779.13, that's toward the low end of the year-round range and worth acting on quickly.
Should I buy a 2026 Toyota Highlander or consider a different year?
If you're weighing the 2026 against nearby model years, here's how to think about it:
Choose the 2026 if:
- 32.4% of listings are priced as good or great deals.
- Accident-free inventory is excellent at 94.5% — clean inventory, standard diligence applies.
The bottom line: If you want the newest version in this year-specific market and value a strong mix of comfort, safety, and practicality, the 2026 Toyota Highlander is the primary path to consider. If you’re more price-sensitive, a nearby model year may give you a lower entry point while still keeping the Highlander’s core family-friendly strengths.
These recommendations are based on CarGurus' proprietary market data from July 22, 2026, CarGurus experts' opinions, and generative AI.
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