Used 2025 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:
- 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


Sponsored by Victory Honda of Michigan City
2025 Toyota Highlander
XLE AWD
18,171 mi
$44,061
- 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:
- Blue
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 36,979
- Stock #:
- 62323
- VIN:
- 5TDKDRAH1SS552015

Sponsored Listing
2025 Toyota Highlander
LE FWD
36,979 mi
$35,099
- 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:
- Black
- Combined gas mileage:
- 25 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 52,599
- Stock #:
- XP21799
- VIN:
- 5TDKDRAH6RS534037

Sponsored Listing
2024 Toyota Highlander
LE FWD
52,599 mi
$30,358
- 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:
- 25,104
- Stock #:
- P7352
- VIN:
- 5TDKDRBH5SS583265

-$2,066
2025 Toyota Highlander
XSE AWD
25,104 mi
$42,010
$39,944
- 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
- Transmission:
- 8-Speed Automatic
- Mileage:
- 26,568
- Stock #:
- 13064P
- VIN:
- 5TDKDRBH4RS537260

2024 Toyota Highlander
XLE AWD
26,568 mi
$41,366
- 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
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Cockpit Red
- Transmission:
- 8-Speed Automatic
- Mileage:
- 38,388
- Stock #:
- MX4769
- VIN:
- 5TDKDRBH3RS548623

2024 Toyota Highlander
XSE AWD
38,388 mi
$40,027
- 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:
- Celestial Silver Metallic
- Combined gas mileage:
- 25 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 57,182
- Stock #:
- V3972
- VIN:
- 5TDKDRAH3RS537994

2024 Toyota Highlander
LE FWD
57,182 mi
$28,296
- 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:
- White (Wind Chill Pearl)
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Transmission:
- 8-Speed Automatic
- Mileage:
- 10,383
- Stock #:
- TR43791
- VIN:
- 5TDKDRBH5SS590961

2025 Toyota Highlander
XLE AWD
10,383 mi
$47,366
- 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
- Transmission:
- 8-Speed Automatic
- Mileage:
- 28,505
- Stock #:
- 13080P
- VIN:
- 5TDKDRBH6RS542914

2024 Toyota Highlander
XLE AWD
28,505 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:
- 37,357
- Stock #:
- 13042P
- VIN:
- 5TDKDRBH2SS588794

2025 Toyota Highlander
LE AWD
37,357 mi
$39,366
- 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
$36,198
- 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:
- Pearl
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- Automatic
- Mileage:
- 4,043
- Stock #:
- 28689703
- VIN:
- 5TDKDRBH8TS596836

2026 Toyota Highlander
Platinum AWD
4,043 mi
$54,747
CarGurus Analysis:
2025 Toyota Highlander
With 93 currently listed for sale near Chicago, IL and an average price of $39,522.00, 43.0% 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.
- 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:
- 32,129
- Stock #:
- XXP21819
- VIN:
- 5TDKDRBHXRS560770

2024 Toyota Highlander
LE AWD
32,129 mi
$33,858
- 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:
- 38,500
- Stock #:
- 28845391
- VIN:
- 5TDKDRBH9RS537013

2024 Toyota Highlander
XSE AWD
38,500 mi
$41,397
- 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:
- White
- Combined gas mileage:
- 25 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 39,731
- Stock #:
- 70179854
- VIN:
- 5TDKDRAH5RS532960

2024 Toyota Highlander
XLE FWD
39,731 mi
$37,397
- 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
$42,113
- 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

2025 Toyota Highlander
XSE AWD
19,572 mi
$43,238
- 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:
- Black
- Combined gas mileage:
- 25 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 52,599
- Stock #:
- XP21799
- VIN:
- 5TDKDRAH6RS534037

2024 Toyota Highlander
LE FWD
52,599 mi
$30,358
- 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:
- 12,560
- Stock #:
- TR43648
- VIN:
- 5TDKDRBH3SS589680

2025 Toyota Highlander
XLE AWD
12,560 mi
$46,366
- 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:
- Red (Ruby Flare Pearl)
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 16,028
- Stock #:
- SP533798
- VIN:
- 5TDKDRBH7RS533798

2024 Toyota Highlander
XSE AWD
16,028 mi
$45,285
- 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:
- 29,913
- Stock #:
- 28207718
- VIN:
- 5TDKDRBH5SS586005

2025 Toyota Highlander
XSE AWD
29,913 mi
$43,997
- 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:
- 28,817
- Stock #:
- 61923
- VIN:
- 5TDKDRAH2SS554968

Sponsored Listing
2025 Toyota Highlander
LE FWD
28,817 mi
$35,898
CarGurus Analysis: 2025 Toyota Highlander

Summary
With 93 currently listed for sale near Chicago, IL and an average price of $39,522.00, 43.0% 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.
Why it stands out
The 2025 Toyota Highlander stands out as a practical, comfort-focused midsize SUV with a long reputation for reliability and strong resale value. It is part of the fourth generation, which brought more upscale styling and interior features, and Toyota reinforced the body to make it more comfortable on the road. The Highlander’s appeal has always been its ability to do family duty well: it offers a smooth ride, useful versatility, and the kind of everyday refinement that makes it easy to live with.
For 2025, the Highlander continues to offer both gas and hybrid powertrains, with front-wheel drive standard and all-wheel drive optional. The hybrid can deliver 35 mpg combined, which is much more than most other midsize SUVs, very few of which offer conventional hybrid drivetrains. Cargo space is another strength, with up to 84.3 cubic feet available with the seats folded down. Every Highlander also comes with an 8-inch touchscreen, Apple CarPlay, Android Auto, Amazon Alexa, and Toyota Safety Sense, giving it a solid mix of convenience and safety equipment.
Its main drawbacks are familiar ones. The Highlander is not especially exciting to drive, and Toyota’s tech remains a hassle to use. The third row is also described as tiny, so buyers who need true adult-sized seating in the back may want to look elsewhere. Even so, the 2025 Highlander remains appealing because it combines comfort, efficiency, practicality, and a strong safety and reliability record in a package that has long been one of the most sensible choices in its class.
Other model years to consider
- Average price: $38,796.00
- Good/great deal percentage: 49.3%
- User rating: 5 / 5
- Total listings: 209
- Average price: $33,633.00
- Good/great deal percentage: 51.4%
- User rating: 4.75 / 5
- Total listings: 255
- Average price: $30,563.00
- Good/great deal percentage: 36.8%
- User rating: 4.86 / 5
- Total listings: 242
This analysis is based on CarGurus' proprietary market data from August 11, 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 trends2025 Toyota Highlander Pricing Analysis: Chicago, IL Market Report
Pricing by Nearby Locations
Market Area: Chicago, IL
Key Insights
- Highest Prices in South Bend, IN: The market in South Bend shows the highest average price at $44,752, likely due to limited inventory and higher demand.
- Lowest Prices in Palatine and Aurora, IL: Both Palatine and Aurora have the lowest average price at $38,264, indicating a more competitive market with higher inventory levels.
- Inventory Variation: Cities like Kenosha, WI (91 listings) and Rockford, IL (56 listings) show moderate pricing, suggesting a balance between supply and demand.
City-Level Pricing
| City | Total Listings | Avg Price |
|---|---|---|
| South Bend, IN | 52 | $44,752 |
| Rockford, IL | 56 | $43,500 |
| Kenosha, WI | 91 | $39,004 |
| Palatine, IL | 94 | $38,264 |
| Aurora, IL | 98 | $38,264 |
Pricing by Trim Packages
Key Insights
- AWD Trims Lead Inventory: The XLE AWD trim is the most common with 272 listings, reflecting strong demand for all-wheel drive options.
- Premium Pricing for Limited Trims: The Limited AWD trim, priced at $49,525 MSRP, commands a significant premium, indicating a market preference for luxury features.
- Value in Base Trims: The LE AWD trim, with 47 listings and a $41,920 MSRP, offers a competitive entry point for buyers seeking AWD capabilities without the luxury markup.
Trim-Level Details
| Trim | Listings | MSRP | Drivetrain | Engine |
|---|---|---|---|---|
| XLE AWD | 272 | $45,070 | AWD | 2.4L 265 hp I4 |
| Limited AWD | 121 | $49,525 | AWD | 2.4L 265 hp I4 |
| XLE FWD | 55 | $43,470 | FWD | 2.4L 265 hp I4 |
| LE AWD | 47 | $41,920 | AWD | 2.4L 265 hp I4 |
| LE FWD | 35 | $40,320 | FWD | 2.4L 265 hp I4 |
| XSE AWD | 51 | $47,140 | AWD | 2.4L 265 hp I4 |
| Platinum AWD | 44 | $52,725 | AWD | 2.4L 265 hp I4 |
| Limited FWD | 23 | $47,575 | FWD | 2.4L 265 hp I4 |
Pricing Analysis by Model Year
Key Insights
- New Model Premium: The 2026 Highlander is priced at $51,469, reflecting a 10.5% premium over its MSRP, indicating strong demand for the latest model.
- Depreciation Trends: The 2019 Highlander shows a significant depreciation of -26.8%, suggesting that older models are becoming more affordable as newer models enter the market.
- Best Value Years: The 2024 Highlander is priced slightly below its MSRP at $39,035, making it a compelling option for buyers looking for a recent model with less depreciation.
Model Year Pricing
| Model Year | Original MSRP | Avg Price | Price vs MSRP |
|---|---|---|---|
| 2026 Toyota Highlander | $46,270 | $51,469 | +10.5% |
| 2024 Toyota Highlander | $39,270 | $39,035 | -0.6% |
| 2023 Toyota Highlander | $36,620 | $33,580 | -8.3% |
| 2022 Toyota Highlander | $35,855 | $32,589 | -9.4% |
| 2021 Toyota Highlander | $35,085 | $30,487 | -13.1% |
| 2020 Toyota Highlander | $34,600 | $26,280 | -24.1% |
| 2019 Toyota Highlander | $31,830 | $23,312 | -26.8% |
| 2018 Toyota Highlander | $31,230 | $21,142 | -32.3% |
| 2017 Toyota Highlander | $30,630 | $20,426 | -33.4% |
| 2016 Toyota Highlander | $30,490 | $19,351 | -36.5% |
| 2015 Toyota Highlander | $29,765 | $18,749 | -37.1% |
These recommendations are based on CarGurus' proprietary market data from August 13, 2026, CarGurus experts' opinions, and generative AI.
How much does the 2025 Toyota Highlander cost?
| Metric | Value |
|---|---|
| Current Average Price | $42,366 |
| Year-Round Low | $39,499.49 |
| Year-Round High | $46,597.53 |
| Average Price a Year Ago | $46,569 |
| Change vs. Last Year | −9.02% |
Prices have softened 9.02% compared to this time last year, making it a favorable time to shop this model year.
There are 1,755 listings available, which gives you a solid amount of inventory to compare before you buy.
If you find a listing below $39,499.49, that's toward the low end of the year-round range and worth acting on quickly.
Is the 2025 Toyota Highlander a good car?
The 2025 Toyota Highlander stands out in the crowded midsize SUV market due to its blend of reliability, comfort, and practicality. The Highlander offers a car-like driving experience with the spaciousness of an SUV, and its well-designed interior accommodates up to seven passengers, making it a strong fit for families. Its soft suspension supports a smooth ride, and the hybrid options add excellent fuel efficiency without sacrificing performance. 34.4% of listings are priced as good or great deals, which gives you some room to shop selectively.
Is the 2025 Toyota Highlander reliable?
The 2025 Toyota Highlander stands out in the crowded midsize SUV market due to its blend of reliability, comfort, and practicality. The Highlander has a reputation for being a dependable family vehicle, with a smooth ride and a practical layout that suits everyday use. Its hybrid options also help broaden its appeal if you want efficiency alongside utility. For used buyers, long-term ownership risk should stay relatively manageable if you focus on condition and maintenance history.
What should I look for when buying a used 2025 Toyota Highlander?
Accident-free inventory is excellent at 92.3% — clean inventory, standard diligence applies.
You should still run a vehicle history report and verify that the specific listing matches the seller’s claims. Prioritize a pre-purchase inspection, especially if you plan to keep the SUV long term or drive it heavily. Focus on overall condition, maintenance records, and signs of wear that could affect comfort, reliability, or resale value.
Is now a good time to buy a used 2025 Toyota Highlander?
This looks like a moderate, selective buyer’s market, so you can shop patiently while still moving quickly on the best-priced examples.
- Deal availability: 34.4% of listings are priced as good or great deals.
- Inventory: There are 1,755 listings available.
- Price trend: Prices have softened 9.02% compared with last year.
- Clean inventory: 92.3% of listings are accident-free.
If you find a listing below $39,499.49, that's toward the low end of the year-round range and worth acting on quickly.
What is the 2025 Toyota Highlander's resale value?
The current average of $42,366 sits slightly below last year's $46,569.
That price movement suggests the market has cooled enough to give you a better entry point than a year ago. If you buy well now and keep the SUV in strong condition, you should be in a better position to preserve value later. The Highlander’s broad family appeal and reputation for practicality should help support resale demand, especially for clean, well-maintained examples.
Should I buy a 2025 Toyota Highlander or consider a different year?
If you're weighing the 2025 against nearby model years, here's how to think about it:
Choose the 2025 if:
- 34.4% of listings are priced as good or great deals.
- Accident-free inventory is excellent at 92.3% — clean inventory, standard diligence applies.
- Price trend: Prices have softened 9.02% compared with last year.
The bottom line: The 2025 Highlander is the better choice if you want a current-year used SUV with strong practicality, a comfortable ride, and a market that gives you some negotiating room. If you’re especially price-sensitive, a nearby model year may be worth comparing, but the 2025 is the cleaner primary target when you want a balanced mix of value, inventory, and family-friendly usability.
These recommendations are based on CarGurus' proprietary market data from August 14, 2026, CarGurus experts' opinions, and generative AI.
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