New & Used 2025 Toyota Highlander for Sale nearChicago, IL
110 vehicles found
- Year:
- 2024
- 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:
- Brown (Harvest Beige)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 48,579
- Stock #:
- H9722
- VIN:
- 5TDKDRBHXRS538235
Price drop
-$1,000
Sponsored by Chicago Auto Place
2024 Toyota Highlander
XLE AWD
48,579 mi
Downers Grove, IL
22 mi away
Good Deal
$38,256
$37,256
- 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
New arrival
Sponsored Listing
2025 Toyota Highlander
XLE AWD
33,609 mi
Hodgkins, IL
15 mi away
Fair Deal
$43,879
- Year:
- 2024
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Gray
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 58,821
- Stock #:
- XP17022
- VIN:
- 5TDKDRBH6RS546820
Sponsored Listing
2024 Toyota Highlander
LE AWD
58,821 mi
Chicago, IL
8 mi away
Fair Deal
$30,868
- 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 #:
- 93F03513
- VIN:
- 5TDKDRBH6SS586062
2025 Toyota Highlander
XLE AWD
18,171 mi
Highland, IN
25 mi away
Great Deal
$42,112
- Year:
- 2024
- 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:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 65,288
- Stock #:
- 534610C01
- VIN:
- 5TDKDRBH1RS534610
2024 Toyota Highlander
LE AWD
65,288 mi
Home delivery from Bedford, OH
Price includes $476 shipping
Great Deal
$28,466
- Year:
- 2024
- 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:
- 32,205
- Stock #:
- P21489
- VIN:
- 5TDKDRBHXRS554788
2024 Toyota Highlander
LE AWD
32,205 mi
Streamwood, IL
32 mi away
Good Deal
$33,358
- 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
Crystal Lake, IL
43 mi away
Great Deal
$44,254
- Year:
- 2024
- 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:
- 48,102
- Stock #:
- K6133A
- VIN:
- 5TDKDRBH1RS541623
2024 Toyota Highlander
XSE AWD
48,102 mi
Fox Lake, IL
45 mi away
Fair Deal
$39,359
- 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
Libertyville, IL
31 mi away
Good Deal
$43,934
- Year:
- 2024
- 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:
- 8-Speed Automatic
- Mileage:
- 38,081
- Stock #:
- NV561279
- VIN:
- 5TDKDRBH2RS561279
2024 Toyota Highlander
Limited AWD
38,081 mi
Home delivery from West Park, FL
Price includes $1,176 shipping
Great Deal
$38,207
- Year:
- 2024
- 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:
- 50,599
- Stock #:
- P16940
- VIN:
- 5TDKDRBH9RS561747
2024 Toyota Highlander
XSE AWD
50,599 mi
Chicago, IL
8 mi away
Good Deal
$39,368
- Year:
- 2024
- 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:
- 45,673
- Stock #:
- XP21817
- VIN:
- 5TDKDRBH1RS551925
2024 Toyota Highlander
LE AWD
45,673 mi
Streamwood, IL
32 mi away
Fair Deal
$32,558
- Year:
- 2024
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Midnight Black Metal
- Combined gas mileage:
- 25 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 51,861
- Stock #:
- 25052
- VIN:
- 5TDKDRAH9RS527745
2024 Toyota Highlander
XSE FWD
51,861 mi
Home delivery from Marietta, GA
Price includes $719 shipping
Fair Deal
$37,518
CarGurus Analysis:
2025 Toyota Highlander
With 102 currently listed for sale near Chicago, IL and an average price of $39,400.00, 43.1% of 2025 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
100.0% of 2025 Highlander models on CarGurus are accident free.
The 2025 Toyota Highlander continues to be a leader in reliability, comfort, and safety, making it a favored choice among families.
- Year:
- 2024
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Cypress
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray (Graphite)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 34,572
- Stock #:
- TW306092A
- VIN:
- 5TDKDRBH8RS547581
2024 Toyota Highlander
Limited AWD
34,572 mi
Home delivery from Palmetto Bay, FL
Free home delivery
Great Deal
$39,798
- Year:
- 2024
- 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:
- 50,121
- Stock #:
- P21475
- VIN:
- 5TDKDRBH3RS550954
2024 Toyota Highlander
LE AWD
50,121 mi
Streamwood, IL
32 mi away
Good Deal
$31,158
- 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
Home delivery from Delaware, OH
Price includes $395 shipping
Great Deal
$36,643
- 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:
- Cement
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 11,369
- Stock #:
- PM589245
- VIN:
- 5TDKDRBH7SS589245
2025 Toyota Highlander
XSE AWD
11,369 mi
Home delivery from Pleasantville, NJ
Price includes $1,292 shipping
Good Deal
$45,742
- Year:
- 2024
- 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:
- 49,121
- Stock #:
- XP16914
- VIN:
- 5TDKDRBH6RS546512
2024 Toyota Highlander
LE AWD
49,121 mi
Chicago, IL
8 mi away
Good Deal
$31,868
- Year:
- 2024
- 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:
- 55,496
- Stock #:
- P21482
- VIN:
- 5TDKDRBHXRS535688
2024 Toyota Highlander
LE AWD
55,496 mi
Streamwood, IL
32 mi away
Good Deal
$30,358
- Year:
- 2024
- 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:
- Brown (Harvest Beige)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 48,579
- Stock #:
- H9722
- VIN:
- 5TDKDRBHXRS538235
Price drop
-$1,000
2024 Toyota Highlander
XLE AWD
48,579 mi
Downers Grove, IL
22 mi away
Good Deal
$38,256
$37,256
- Year:
- 2024
- 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:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 55,834
- Stock #:
- DT1354A
- VIN:
- 5TDKDRBH5RS575239
2024 Toyota Highlander
XLE AWD
55,834 mi
Niles, IL
12 mi away
Fair Deal
$38,373
- Year:
- 2024
- 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:
- 39,385
- Stock #:
- P21557
- VIN:
- 5TDKDRBH5RS552821
2024 Toyota Highlander
XLE AWD
39,385 mi
Streamwood, IL
32 mi away
Good Deal
$37,858
- Year:
- 2024
- 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:
- 50,599
- Stock #:
- P16940
- VIN:
- 5TDKDRBH9RS561747
Sponsored Listing
2024 Toyota Highlander
XSE AWD
50,599 mi
Chicago, IL
8 mi away
Good Deal
$39,368
CarGurus Analysis: 2025 Toyota Highlander
Summary
With 102 currently listed for sale near Chicago, IL and an average price of $39,400.00, 43.1% of 2025 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
100.0% of 2025 Highlander models on CarGurus are accident free.
The 2025 Toyota Highlander continues to be a leader in reliability, comfort, and safety, making it a favored choice among families.
Why it stands out
The 2025 Toyota Highlander maintains its reputation as a top contender in the midsize SUV category, characterized by its spacious interior and excellent safety ratings. It offers a comfortable driving experience with reliable performance, enhanced by the recent introduction of a hybrid option that maximizes fuel efficiency. The Highlander's blend of practicality and advanced safety features, such as Toyota Safety Sense, ensures peace of mind for families and daily commuters alike. However, while it excels in offering a smooth ride and ample passenger space, it might not be the most exciting vehicle to drive, with a softer suspension and less engaging handling compared to some rivals. Overall, buyers appreciate its versatility, robust reliability, and strong resale values.
Other model years to consider
- Average price: $36,506.00
- Good/great deal percentage: 51.7%
- User rating: 5 / 5
- Total listings: 209
- Average price: $35,748.00
- Good/great deal percentage: 50.8%
- User rating: 4.75 / 5
- Total listings: 258
- Average price: $30,111.00
- Good/great deal percentage: 37.2%
- User rating: 4.86 / 5
- Total listings: 234
This analysis is based on CarGurus' proprietary market data from June 23, 2026, CarGurus experts' opinions, and generative AI.
2025 Toyota Highlander Trims
| Trim type | MSRP |
|---|---|
| LE FWD | $40,320 |
| Limited FWD | $47,575 |
| Limited AWD | $49,525 |
| LE AWD | $41,920 |
| Platinum AWD | $52,725 |
| XSE AWD | $47,140 |
| XLE AWD | $45,070 |
| XLE FWD | $43,470 |
2025 Toyota Highlander Price Trends
CarGurus tracks the prices of millions of used car listings every year. See how the average price of 2025 Toyota Highlander prices has changed over time.
See more price trendsAVG Price
$41,848
0.2%
2025 Toyota Highlander
Index Price
$29,175
0.2%
All used vehicles
2025 Toyota Highlander Pricing Analysis: Chicago, IL Market Report
Pricing by Nearby Locations
Market Area: Chicago, IL
Key Insights
- Highest Prices in Holland, MI: The city reports an average price of $46,359, indicating strong demand or limited supply in that area.
- Lowest Priced Local Market: South Bend, IN ($44,857) presents a more competitive pricing option, suggesting a different supply-demand dynamic compared to markets like Holland.
- Consistent Pricing Across Region: Most nearby cities hover around the $38,904 average, which reflects stable pricing in a well-supplied market.
City-Level Pricing
| City | Total Listings | Avg Price |
|---|---|---|
| Holland, MI | 56 | $46,359 |
| South Bend, IN | 62 | $44,857 |
| Rockford, IL | 65 | $40,869 |
| Kenosha, WI | 116 | $38,326 |
| Aurora, IL | 104 | $38,904 |
| Milwaukee, WI | 76 | $38,993 |
| Palatine, IL | 100 | $38,904 |
| Janesville, WI | 63 | $41,375 |
| Lafayette, IN | 76 | $40,485 |
| Kalamazoo, MI | 64 | $45,585 |
Pricing by Trim Packages
Key Insights
- XLE AWD is the Most Available: With 263 listings, this trim dominates the inventory and serves as a key reference point for pricing.
- Limited AWD Commands the Highest Price: Priced at $49,525 MSRP, it reflects the premium features and high demand for this trim.
- Competitive Entry Pricing for LE Trims: The LE FWD at $40,320 MSRP represents a more budget-friendly option for consumers prioritizing cost.
Trim-Level Details
| Trim | Listings | MSRP | Drivetrain | Engine |
|---|---|---|---|---|
| XLE AWD | 263 | $45,070 | AWD | 2.4L 265 hp I4 |
| Limited AWD | 108 | $49,525 | AWD | 2.4L 265 hp I4 |
| LE AWD | 64 | $41,920 | AWD | 2.4L 265 hp I4 |
| XLE FWD | 63 | $43,470 | FWD | 2.4L 265 hp I4 |
| LE FWD | 42 | $40,320 | FWD | 2.4L 265 hp I4 |
| XSE AWD | 47 | $47,140 | AWD | 2.4L 265 hp I4 |
| Platinum AWD | 40 | $52,725 | AWD | 2.4L 265 hp I4 |
| Limited FWD | 25 | $47,575 | FWD | 2.4L 265 hp I4 |
Pricing Analysis by Model Year
Key Insights
- New Model Year at a Premium: The 2026 Toyota Highlander is priced at $49,880, indicating a 8.1% premium over its starting MSRP, reflecting strong demand for the latest model.
- Significant Depreciation for Older Models: The 2019 Highlander shows a steep decline with an average price of $24,702, translating to a -22.4% depreciation from its original MSRP.
- Best Value in 2022 Models: The 2022 Highlander at $33,705 is currently -6.4% below MSRP, making it an attractive option for buyers seeking newer vehicles without the price tag of the latest models.
Model Year Pricing
| Model Year | Original MSRP | Avg Price | Price vs MSRP |
|---|---|---|---|
| 2026 Toyota Highlander | $45,870 | $49,880 | +8.1% |
| 2024 Toyota Highlander | $39,270 | $38,580 | -1.8% |
| 2023 Toyota Highlander | $36,620 | $35,627 | -2.7% |
| 2022 Toyota Highlander | $35,855 | $33,705 | -6.4% |
| 2021 Toyota Highlander | $35,085 | $30,123 | -14.1% |
| 2020 Toyota Highlander | $34,600 | $27,493 | -20.5% |
| 2019 Toyota Highlander | $31,830 | $24,702 | -22.4% |
| 2018 Toyota Highlander | $31,230 | $22,613 | -27.6% |
| 2017 Toyota Highlander | $30,630 | $20,159 | -34.1% |
| 2016 Toyota Highlander | $30,490 | $19,171 | -37.1% |
| 2015 Toyota Highlander | $29,765 | $17,744 | -40.4% |
These recommendations are based on CarGurus' proprietary market data from June 25, 2026, CarGurus experts' opinions, and generative AI.
FAQs
How much does the 2025 Toyota Highlander cost in Chicago, IL?
The average 2025 Toyota Highlander costs about $41,848.18. The average price has increased by 0.6% since last year. The 90 for sale near Chicago, IL on CarGurus, range from $28,466 to $55,860 in price.
How many 2025 Toyota Highlander vehicles in Chicago, IL have no reported accidents or damage?
90 out of 90 for sale near Chicago, IL have no reported accidents or damage.
What is the fuel economy of the 2025 Toyota Highlander?
Depending on the engine and options, the 2025 Toyota Highlander gets between 24 and 25 MPG (or EV battery range).
What fuel types are available?
Gasoline engines are available.
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