Used Toyota Highlander for Sale nearChicago, IL
340 vehicles found
- Year:
- 2021
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Midnight Black Metallic
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 62,322
- Stock #:
- G2835A
- VIN:
- 5TDGZRBH7MS108209
Sponsored by Genesis of Aurora
2021 Toyota Highlander
XLE AWD
62,322 mi
$28,889
- Year:
- 2021
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Red (Ruby Flare Pearl)
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Brown (Harvest Beige)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 85,984
- Stock #:
- MK260471A
- VIN:
- 5TDGZRBH6MS554383
Sponsored Listing
2021 Toyota Highlander
XLE AWD
85,984 mi
$29,210
- Year:
- 2008
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Exterior color:
- Black
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 5-Speed Automatic Overdrive
- Mileage:
- 143,299
- Stock #:
- 3683
- VIN:
- JTEES42A982021521
Sponsored Listing
2008 Toyota Highlander
Limited 4WD
143,299 mi
$10,150
- Year:
- 2023
- 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:
- 31,094
- Stock #:
- 28630314
- VIN:
- 5TDKDRAH9PS003749
2023 Toyota Highlander
L FWD
31,094 mi
$32,797
- Year:
- 2016
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Exterior color:
- Midnight Black Metallic
- Fuel type:
- Gasoline
- Interior color:
- Ash
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 70,088
- Stock #:
- X026945A
- VIN:
- 5TDDKRFH2GS281125
2016 Toyota Highlander
Limited Platinum AWD
70,088 mi
$24,763
- Year:
- 2022
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Midnight Black Metallic
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Brown (Harvest Beige)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 68,265
- Stock #:
- 27028I
- VIN:
- 5TDDZRBH9NS191582
2022 Toyota Highlander
Limited AWD
68,265 mi
$31,902
- Year:
- 2022
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Midnight Black Metallic
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 50,689
- Stock #:
- P7340
- VIN:
- 5TDDZRBH6NS576243
2022 Toyota Highlander
Limited AWD
50,689 mi
$35,969
- Year:
- 2018
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Gray
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 69,652
- Stock #:
- 261445A
- VIN:
- 5TDJZRFH3JS889824
2018 Toyota Highlander
SE AWD
69,652 mi
$26,867
- Year:
- 2023
- 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:
- Gray (Graphite)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 51,384
- Stock #:
- N2640056A
- VIN:
- 5TDKDRBH4PS504790
2023 Toyota Highlander
LE AWD
51,384 mi
$30,395
- Year:
- 2021
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Magnetic Gray Metallic
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 76,536
- Stock #:
- 469771
- VIN:
- 5TDDZRBH0MS127624
2021 Toyota Highlander
Limited AWD
76,536 mi
$32,377
- Year:
- 2010
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Exterior color:
- White
- Fuel type:
- Gasoline
- Interior color:
- Ash
- Transmission:
- 5-Speed Automatic Overdrive
- Mileage:
- 138,207
- Stock #:
- JU18223A
- VIN:
- 5TDJK3EH6AS009752
2010 Toyota Highlander
SE 4WD
138,207 mi
$10,173
- Year:
- 2021
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Blueprint
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray (Graphite)
- Transmission:
- Automatic
- Mileage:
- 62,803
- Stock #:
- PH1896
- VIN:
- 5TDGZRBH6MS136860
2021 Toyota Highlander
XLE AWD
62,803 mi
$30,050
- Year:
- 2023
- 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:
- 72,825
- Stock #:
- P1686
- VIN:
- 5TDKDRBH3PS511522
2023 Toyota Highlander
XLE AWD
72,825 mi
$33,213
Recommended model year:
2024 Toyota Highlander
Shop 2024 Toyota Highlander »With 192 currently listed for sale near Chicago, IL and an average price of $36,482.00, 50.0% of 2024 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
Favorably reviewed: Owners rated the 2024 Toyota Highlander 5 / 5 stars.
100.0% of 2024 Highlander models on CarGurus are accident free.
The 2024 Toyota Highlander features a spacious interior, advanced safety technology, and a smooth ride, making it an excellent choice for families.
- Year:
- 2015
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Exterior color:
- Predawn Gray Mica
- Fuel type:
- Gasoline
- Interior color:
- Ash
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 124,423
- Stock #:
- KH1197
- VIN:
- 5TDBKRFH1FS106273
2015 Toyota Highlander
LE Plus AWD
124,423 mi
$17,390
- Year:
- 2017
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- White
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 104,993
- Stock #:
- N513252
- VIN:
- 5TDJZRFH9HS513252
2017 Toyota Highlander
XLE AWD
104,993 mi
$20,900
- Year:
- 2020
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Moon Dust
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- 8-Speed Automatic
- Mileage:
- 59,717
- Stock #:
- XBP8521
- VIN:
- 5TDGZRBH0LS013005
2020 Toyota Highlander
XLE AWD
59,717 mi
$29,740
- Year:
- 2019
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- White (Blizzard Pearl)
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 90,906
- Stock #:
- 27000A
- VIN:
- 5TDJZRFH5KS629393
2019 Toyota Highlander
XLE AWD
90,906 mi
$24,164
- Year:
- 2021
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Magnetic Gray Metallic
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray (Graphite)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 81,199
- Stock #:
- PS3791
- VIN:
- 5TDGZRBH6MS103048
2021 Toyota Highlander
XLE AWD
81,199 mi
$27,708
- Year:
- 2023
- 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:
- 45,265
- Stock #:
- D68658A
- VIN:
- 5TDKDRAH5PS508879
2023 Toyota Highlander
XSE FWD
45,265 mi
$36,858
- Year:
- 2022
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- White (Wind Chill Pearl)
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray (Graphite)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 22,054
- Stock #:
- X026725XA1
- VIN:
- 5TDFZRBH7NS214141
2022 Toyota Highlander
Platinum AWD
22,054 mi
$43,013
- Year:
- 2018
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Salsa Red Pearl
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 110,228
- Stock #:
- J5536056
- VIN:
- 5TDJZRFH6JS536056
2018 Toyota Highlander
SE AWD
110,228 mi
$22,877
- Year:
- 2021
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Magnetic Gray Metallic
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 88,024
- Stock #:
- MS260221C
- VIN:
- 5TDGZRBH7MS098720
2021 Toyota Highlander
XLE AWD
88,024 mi
$28,710
- 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:
- 29,599
- Stock #:
- 61997
- VIN:
- 5TDKDRAH9SS554028
-$1,924
Sponsored Listing
2025 Toyota Highlander
LE FWD
29,599 mi
$36,373
$34,449
FAQs
How much does the Toyota Highlander cost in Chicago, IL?
How many Toyota Highlander vehicles in Chicago, IL have no reported accidents or damage?
What fuel types are available?
4.7 Overall rating
Customers say
Overall, the Toyota Highlander has built a strong reputation across its model years for reliability, comfort, and family-friendly features. Drivers appreciate its spacious interiors and smooth rides, often highlighting its impressive safety features as a key asset. Many also enjoy the performance and power of the engines. However, some common criticisms include a lack of advanced infotainment options in older models, tight third-row seating, and varying cargo space depending on configuration. Overall, the Highlander is seen as a dependable choice for families and an excellent value in the SUV market.
AI generated from the text of customer reviews.
Filter by year
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What people say
Anonymous
Reviewed a 2024 Toyota XLE AWD on Dec 10, 2025
The 2024 Toyota Highlander XLE offers insane cabin room, comfort and luxury feel. The chassis makes an absolute smooth, dream and comfortable ride. Cabin rear chairs makes four adults feel like your in a Sequoia with room. Absolute beautiful and enjoyable ride and purchase
Julie W
Reviewed a 2021 Toyota Highlander on Jul 20, 2024
I loved my Highlander. I give my 2021 Toyota Highlander a 100 out of 10 on its safety. My car was a limited and it had most bells and whistles which I loved but what I loved most was that we all walked away from a collision where we were traveling 40 miles an hour and thanks to the safety design , we’re here.
Luong S
Reviewed a 2012 Toyota Base on Apr 26, 2026
This car's features are very good and have great value the only missing is it has only one key.
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.
Toyota Highlander Trims
| Trim type | MSRP |
|---|---|
| Platinum AWD | $53,925 |
| XLE AWD | $46,270 |
| XSE AWD | $48,340 |
| Limited AWD | $50,725 |
Toyota Highlander Price Trends
CarGurus tracks the prices of millions of used car listings every year. See how the average price of Toyota Highlander prices has changed over time.
See more price trendsToyota Highlander Pricing Analysis: Chicago, IL Market Report
Pricing Analysis by Model Year
Key Insights
- New Model Premium: The 2026 Toyota Highlander is priced at $49,880, which is approximately 7.0% above its MSRP, indicating strong demand for the latest model.
- Significant Depreciation for Older Models: The 2016 Highlander shows the steepest depreciation at −39.5% compared to its original MSRP, reflecting a typical depreciation trend for older vehicles.
- Best Value Years: The 2021 Highlander is priced at $30,781, representing a −12.1% depreciation, making it a potentially attractive option for buyers seeking value.
Model Year Pricing
| Model Year | Original MSRP | Avg Price | Price vs MSRP |
|---|---|---|---|
| 2026 Toyota Highlander | $46,270 | $49,880 | +7.0% |
| 2025 Toyota Highlander | $40,320 | $37,900 | -6.9% |
| 2024 Toyota Highlander | $39,270 | $36,613 | -6.8% |
| 2023 Toyota Highlander | $36,620 | $35,677 | -2.6% |
| 2022 Toyota Highlander | $35,855 | $33,816 | -5.7% |
| 2021 Toyota Highlander | $35,085 | $30,781 | -12.1% |
| 2020 Toyota Highlander | $34,600 | $27,877 | -19.5% |
| 2019 Toyota Highlander | $31,830 | $24,387 | -23.4% |
| 2018 Toyota Highlander | $31,230 | $22,578 | -27.8% |
| 2017 Toyota Highlander | $30,630 | $20,384 | -33.5% |
| 2016 Toyota Highlander | $30,490 | $18,535 | -39.5% |
Pricing in Nearby Cities
Market Area: Greater Chicago Region
Key Insights
- Lowest Prices in Suburban Areas: Palatine, IL offers the lowest average price at $25,451, indicating a more price-sensitive market compared to urban centers.
- Higher Prices in Larger Cities: South Bend, IN has a higher average price of $31,015, likely due to lower inventory and higher demand.
- Inventory Variation: Cities like Aurora, IL and Kenosha, WI have substantial listings (324 and 300 respectively), but their prices remain competitive, suggesting a balanced supply-demand dynamic.
City-Level Pricing
| City | Total Listings | Avg Price |
|---|---|---|
| South Bend, IN | 686 | $31,015 |
| Rockford, IL | 675 | $27,151 |
| Milwaukee, WI | 665 | $27,240 |
| Janesville, WI | 674 | $26,860 |
| Holland, MI | 671 | $26,336 |
| Kalamazoo, MI | 701 | $26,475 |
| Lafayette, IN | 766 | $28,872 |
| Palatine, IL | 334 | $25,451 |
| Aurora, IL | 324 | $25,202 |
| Kenosha, WI | 300 | $27,231 |
Pricing by Trim Packages
Key Insights
- AWD Trims Dominate Listings: The XLE AWD is the most common trim with 255 listings, reflecting strong demand for all-wheel drive options.
- Premium Pricing for Higher Trims: The Limited AWD trim, priced at $50,725, commands a significant premium, indicating a market preference for luxury features.
- Value in Mid-Level Trims: The XSE AWD offers a balance of features and price at $48,340, appealing to buyers seeking a well-equipped vehicle without the highest price tag.
Trim-Level Details
| Trim | Listings | MSRP | Drivetrain | Engine |
|---|---|---|---|---|
| XLE AWD | 255 | $46,270 | AWD | 2.4L 265 hp I4 |
| Limited AWD | 104 | $50,725 | AWD | 2.4L 265 hp I4 |
| XSE AWD | 40 | $48,340 | AWD | 2.4L 265 hp I4 |
| Platinum AWD | 43 | $53,925 | AWD | 2.4L 265 hp I4 |
These recommendations are based on CarGurus' proprietary market data from July 2, 2026, CarGurus experts' opinions, and generative AI.
CarGurus recommends the 2024 Toyota Highlander
Summary
With 192 currently listed for sale near Chicago, IL and an average price of $36,482.00, 50.0% of 2024 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
Favorably reviewed: Owners rated the 2024 Toyota Highlander 5 / 5 stars.
100.0% of 2024 Highlander models on CarGurus are accident free.
The 2024 Toyota Highlander features a spacious interior, advanced safety technology, and a smooth ride, making it an excellent choice for families.
Why it stands out
The 2024 Toyota Highlander continues to build on its reputation as a reliable and family-friendly SUV. With its spacious interior and comfortable seating for up to eight passengers, it caters to families looking for practicality without sacrificing style. The Highlander is equipped with advanced safety features, ensuring peace of mind for drivers and passengers alike. Its smooth ride and efficient powertrains, including hybrid options, make it a versatile choice for various driving needs. Overall, the Highlander stands out for its blend of comfort, safety, and reliability, appealing to those who prioritize these qualities in a midsize SUV.
Other model years to consider
- Average price: $35,578.00
- Good/great deal percentage: 47.7%
- User rating: 4.75 / 5
- Total listings: 237
- Average price: $18,535.00
- Good/great deal percentage: 27.5%
- User rating: 4.93 / 5
- Total listings: 160
- Average price: $30,897.00
- Good/great deal percentage: 33.3%
- User rating: 4.86 / 5
- Total listings: 222
These recommendations are based on CarGurus' proprietary market data from July 1, 2026, CarGurus experts' opinions, and generative AI.
Recent expert test drives
2022 Toyota Highlander
- Expert review8/10
- MSRP$35,855-$49,960
- Avg. price$33,251
- User rating4.4444
2020 Toyota Highlander
- Expert review8/10
- MSRP$34,600-$48,800
- Avg. price$28,151
- User rating4.6
2021 Toyota Highlander
- Expert review8/10
- MSRP$35,085-$49,190
- Avg. price$30,324
- User rating4.8636
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