Used Toyota Highlander for Sale near Chicago, IL
368 results
- 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:
- 62,754
- Stock #:
- 16702
- VIN:
- 5TDHZRBH9NS560409
Sponsored by Driven Auto Sales
2022 Toyota Highlander
XLE AWD
62,754 mi
$33,757
- 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:
- Gray
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 93,891
- Stock #:
- 93480A
- VIN:
- 5TDJZRFH3KS589699
Sponsored Listing
2019 Toyota Highlander
XLE AWD
93,891 mi
$24,907
- 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:
- Celestial Silver Metallic
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 110,981
- Stock #:
- 11209
- VIN:
- 5TDGZRBH2MS542599
Sponsored Listing
2021 Toyota Highlander
XLE AWD
110,981 mi
$28,100
- Year:
- 2018
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Blue
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 99,641
- Stock #:
- 28520857
- VIN:
- 5TDKZRFHXJS265393
2018 Toyota Highlander
XLE
99,641 mi
$23,747
- 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
- Combined gas mileage:
- 21 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 88,789
- Stock #:
- 101444
- VIN:
- 5TDDKRFH1FS122529
2015 Toyota Highlander
Limited AWD
88,789 mi
$19,980
- 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:
- Shoreline Blue Pearl
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 61,211
- Stock #:
- T65878B
- VIN:
- 5TDJZRFH3JS861814
2018 Toyota Highlander
XLE AWD
61,211 mi
$27,278
- 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:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 87,753
- Stock #:
- P12236
- VIN:
- 5TDDKRFH7GS354683
2016 Toyota Highlander
Limited AWD
87,753 mi
$22,668
- Year:
- 2014
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Exterior color:
- Gray
- Combined gas mileage:
- 21 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 135,997
- Stock #:
- K6090A
- VIN:
- 5TDDKRFH5ES046828
-$733
2014 Toyota Highlander
Limited Platinum AWD
135,997 mi
$17,491
$16,758
- 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
$25,213
- Year:
- 2017
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- White (Blizzard Pearl)
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Brown (Tan)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 62,936
- Stock #:
- 10521A
- VIN:
- 5TDYZRFH2HS220159
2017 Toyota Highlander
Limited
62,936 mi
$26,013
- Year:
- 2015
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Exterior color:
- White
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Brown (TAN)
- Transmission:
- 6-Speed Automatic
- Mileage:
- 149,170
- Stock #:
- 3847
- VIN:
- 5TDJKRFH3FS159536
2015 Toyota Highlander
XLE
149,170 mi
$14,064
- 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
$29,110
- 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:
- Midnight Black Metallic
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 10,743
- Stock #:
- P7292
- VIN:
- 5TDKDRBH2PS021606
2023 Toyota Highlander
XLE AWD
10,743 mi
$40,281
Recommended model year:
2024 Toyota Highlander
Shop 2024 Toyota Highlander »With 204 currently listed for sale near Chicago, IL and an average price of $36,370.00, 53.4% 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 and comfortable interior, excellent safety ratings, and advanced technology, making it an ideal family SUV.
- 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
$43,713
- 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:
- Red
- Combined gas mileage:
- 21 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 152,027
- Stock #:
- M6809A
- VIN:
- 5TDBKRFH5GS226949
2016 Toyota Highlander
LE AWD
152,027 mi
$15,497
- 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:
- Celestial Silver Metallic
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 83,483
- Stock #:
- FP0529
- VIN:
- 5TDDZRFH7HS482208
2017 Toyota Highlander
Limited Platinum AWD
83,483 mi
$26,968
- 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
$30,362
- 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:
- Cypress
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 114,069
- Stock #:
- PBA1190A
- VIN:
- 5TDKDRBH5PS502093
2023 Toyota Highlander
LE AWD
114,069 mi
$25,611
- 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
$29,250
- 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:
- Silver Sky Metallic
- Combined gas mileage:
- 21 MPG
- Fuel type:
- Gasoline
- Interior color:
- Ash
- Transmission:
- Automatic
- Mileage:
- 133,294
- Stock #:
- N260221A
- VIN:
- 5TDJKRFH2GS246832
-$557
2016 Toyota Highlander
XLE AWD
133,294 mi
$18,903
$18,346
- 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:
- 2021
- 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:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray (Graphite)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 88,727
- Stock #:
- XBP8554
- VIN:
- 5TDGZRBH9MS105117
2021 Toyota Highlander
XLE AWD
88,727 mi
$28,331
- 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:
- Midnight Black Metallic
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 41,870
- Stock #:
- 69F04524
- VIN:
- 5TDKDRAH3SS550623
Sponsored Listing
2025 Toyota Highlander
LE FWD
41,870 mi
$34,349
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
Filter by rating
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 | $53,525 |
| XLE AWD | $45,870 |
| XSE AWD | $47,940 |
| Limited AWD | $50,325 |
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
- Newer Models at a Premium: The 2026 Highlander is priced at $50,380, reflecting a +9.1% increase over its MSRP, suggesting strong demand for the latest model.
- Significant Depreciation Over Time: The 2016 Highlander shows a steep decline in average price, down to $18,844, representing a -38.5% drop from its original MSRP.
- Best Value in Mid-Year Range: The 2021 Highlander offers considerable value with an average price of $29,723, being -15.9% below MSRP.
Model Year Pricing
| Model Year | Original MSRP | Avg Price | Price vs MSRP |
|---|---|---|---|
| 2026 Toyota Highlander | $45,870 | $50,380 | +9.1% |
| 2025 Toyota Highlander | $40,320 | $39,242 | -2.7% |
| 2024 Toyota Highlander | $39,270 | $36,762 | -6.4% |
| 2023 Toyota Highlander | $36,620 | $35,386 | -3.4% |
| 2022 Toyota Highlander | $35,855 | $33,924 | -5.4% |
| 2021 Toyota Highlander | $35,085 | $29,723 | -15.9% |
| 2020 Toyota Highlander | $34,600 | $27,379 | -20.9% |
| 2019 Toyota Highlander | $31,830 | $24,944 | -21.6% |
| 2018 Toyota Highlander | $31,230 | $23,044 | -26.3% |
| 2017 Toyota Highlander | $30,630 | $20,185 | -34.0% |
| 2016 Toyota Highlander | $30,490 | $18,844 | -38.5% |
Pricing in Nearby Cities
Market Area: Greater Chicago Region
Key Insights
- Palatine Leads in Affordability: Among the cities listed, Palatine, IL ($25,587) offers the lowest average price, likely reflecting local market dynamics and inventory levels.
- South Bend Represents a Middle Ground: With an average price of $29,850 and significant inventory (630 listings), South Bend strikes a balance between supply and cost.
- Higher Prices Elsewhere: Cities like Aurora, IL ($25,362) and Milwaukee, WI ($27,101) show slightly elevated pricing, indicating potential demand pressures in urban centers.
City-Level Pricing
| City | Total Listings | Avg Price |
|---|---|---|
| Palatine, IL | 351 | $25,587 |
| Aurora, IL | 341 | $25,362 |
| Kenosha, WI | 327 | $27,120 |
| South Bend, IN | 630 | $29,850 |
| Rockford, IL | 629 | $25,194 |
| Milwaukee, WI | 646 | $27,101 |
| Janesville, WI | 620 | $24,586 |
| Holland, MI | 621 | $26,045 |
| Kalamazoo, MI | 653 | $26,550 |
| Lafayette, IN | 727 | $28,641 |
Pricing by Trim Packages
Key Insights
- Most Inventory in XLE AWD Trim: The XLE AWD is the most frequently available trim with 247 listings, indicating strong consumer preference for this well-equipped variant.
- Limited AWD at a Premium: The Limited AWD ($50,325 MSRP) stands out as the highest priced trim, reflecting its enhanced luxury features and technology.
- XSE AWD Balances Price and Features: With a MSRP of $47,940, the XSE AWD offers a solid value proposition with ample features while still maintaining reasonable availability.
Trim-Level Details
| Trim | Listings | MSRP | Drivetrain | Engine |
|---|---|---|---|---|
| XLE AWD | 247 | $45,870 | AWD | 2.4L 265 hp I4 |
| Limited AWD | 99 | $50,325 | AWD | 2.4L 265 hp I4 |
| XSE AWD | 42 | $47,940 | AWD | 2.4L 265 hp I4 |
| Platinum AWD | 41 | $53,525 | AWD | 2.4L 265 hp I4 |
These recommendations are based on CarGurus' proprietary market data from June 18, 2026, CarGurus experts' opinions, and generative AI.
CarGurus recommends the 2024 Toyota Highlander
Summary
With 204 currently listed for sale near Chicago, IL and an average price of $36,370.00, 53.4% 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 and comfortable interior, excellent safety ratings, and advanced technology, making it an ideal family SUV.
Why it stands out
The 2024 Toyota Highlander continues to be a leading choice in the midsize SUV segment due to its combination of comfort, reliability, and family-friendly features. This model showcases a refined design while offering versatile seating options and ample cargo space, making it an excellent choice for families and those needing extra room. With a user-friendly infotainment system and highlights such as Toyota Safety Sense providing advanced safety features, the Highlander excels in providing both peace of mind and enjoyable driving experiences. Its impressive reliability and the introduction of efficient hybrid variants ensure that it remains a practical option for buyers looking for a dependable SUV.
Other model years to consider
- Average price: $35,533.00
- Good/great deal percentage: 52.4%
- User rating: 4.75 / 5
- Total listings: 250
- Average price: $18,774.00
- Good/great deal percentage: 31.6%
- User rating: 4.93 / 5
- Total listings: 133
- Average price: $30,321.00
- Good/great deal percentage: 38.4%
- User rating: 4.86 / 5
- Total listings: 224
These recommendations are based on CarGurus' proprietary market data from June 16, 2026, CarGurus experts' opinions, and generative AI.
Recent expert test drives
2022 Toyota Highlander
- Expert review8/10
- MSRP$35,855-$49,960
- Avg. price$33,247
- User rating4.4444
2020 Toyota Highlander
- Expert review8/10
- MSRP$34,600-$48,800
- Avg. price$28,325
- User rating4.6
2021 Toyota Highlander
- Expert review8/10
- MSRP$35,085-$49,190
- Avg. price$30,364
- User rating4.8636
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