Used 2021 Toyota Highlander for Sale nearChicago, IL
222 vehicles found
- Year:
- 2021
- 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:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray (Graphite)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 75,177
- Stock #:
- PC0077
- VIN:
- 5TDZZRAH8MS079331
Sponsored by Dial Chevrolet
2021 Toyota Highlander
LE FWD
75,177 mi
$25,300
- 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:
- 63,867
- Stock #:
- 60633D
- VIN:
- 5TDGZRBH6MS104121
Sponsored Listing
2021 Toyota Highlander
XLE AWD
63,867 mi
$30,995
- Year:
- 2022
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 68,994
- Stock #:
- P21810
- VIN:
- 5TDJZRBH7NS217602
Sponsored Listing
2022 Toyota Highlander
XSE AWD
68,994 mi
$34,358
- 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:
- 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:
- 2021
- 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:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray (Graphite)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 75,177
- Stock #:
- PC0077
- VIN:
- 5TDZZRAH8MS079331
2021 Toyota Highlander
LE FWD
75,177 mi
$25,300
- 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:
- 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:
- 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:
- 8-Speed Automatic
- Mileage:
- 73,400
- Stock #:
- K7277
- VIN:
- 5TDGZRBH4MS550672
2021 Toyota Highlander
XLE AWD
73,400 mi
$28,898
- 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:
- 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
-$800
2021 Toyota Highlander
XLE AWD
81,199 mi
$28,413
$27,613
- 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:
- Black
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 108,307
- Stock #:
- b148847
- VIN:
- 5TDGZRBH8MS148847
2021 Toyota Highlander
XLE AWD
108,307 mi
$26,875
CarGurus Analysis:
2021 Toyota Highlander
With 234 currently listed for sale near Chicago, IL and an average price of $30,111.00, 37.2% of 2021 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
Favorably reviewed: Owners rated the 2021 Toyota Highlander 4.86 / 5 stars.
100.0% of 2021 Highlander models on CarGurus are accident free.
The 2021 Toyota Highlander features a spacious interior with high-quality materials, a smooth ride, and advanced safety technology, making it a top choice for families.
- Year:
- 2021
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 73,895
- Stock #:
- S086453
- VIN:
- 5TDZZRAH2MS086453
-$500
2021 Toyota Highlander
LE FWD
73,895 mi
$23,515
$23,014
- 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:
- 2022
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Black
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 33,696
- Stock #:
- 70008433
- VIN:
- 5TDHZRBHXNS224977
2022 Toyota Highlander
XLE AWD
33,696 mi
$37,897
- 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:
- Blue
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- Automatic
- Mileage:
- 52,656
- Stock #:
- P21681
- VIN:
- 5TDGZRBHXNS248790
2022 Toyota Highlander
XLE AWD
52,656 mi
$33,658
- 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
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 72,299
- Stock #:
- P21634
- VIN:
- 5TDJZRBH3MS112246
2021 Toyota Highlander
XSE AWD
72,299 mi
$32,358
- 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:
- Automatic
- Mileage:
- 76,945
- Stock #:
- P12048
- VIN:
- 5TDFZRBH0MS092320
2021 Toyota Highlander
Platinum AWD
76,945 mi
$35,257
- 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:
- Gray (Graphite)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 74,573
- Stock #:
- PA0806
- VIN:
- 5TDGZRBH3MS538254
2021 Toyota Highlander
XLE AWD
74,573 mi
$29,336
- Year:
- 2022
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 52,433
- Stock #:
- S20248A
- VIN:
- 5TDGZRBH8NS229719
2022 Toyota Highlander
XLE AWD
52,433 mi
$35,008
- Year:
- 2020
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- White
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Brown (Tan)
- Transmission:
- Automatic
- Mileage:
- 66,785
- Stock #:
- S006528
- VIN:
- 5TDYZRAH0LS006528
2020 Toyota Highlander
Limited FWD
66,785 mi
$30,148
- 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:
- Black
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 71,575
- Stock #:
- D68534A
- VIN:
- 5TDFZRBH9NS191557
Sponsored Listing
2022 Toyota Highlander
Platinum AWD
71,575 mi
$36,858
CarGurus Analysis: 2021 Toyota Highlander
overall
Summary
With 234 currently listed for sale near Chicago, IL and an average price of $30,111.00, 37.2% of 2021 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
Favorably reviewed: Owners rated the 2021 Toyota Highlander 4.86 / 5 stars.
100.0% of 2021 Highlander models on CarGurus are accident free.
The 2021 Toyota Highlander features a spacious interior with high-quality materials, a smooth ride, and advanced safety technology, making it a top choice for families.
Why it stands out
The 2021 Toyota Highlander is a standout option in the competitive three-row SUV market, thanks to its combination of comfort, safety features, and reliability. With an impressive 295 horsepower generated by a 3.5-liter V6 engine paired with an eight-speed automatic transmission, the Highlander delivers satisfactory performance for daily driving and family trips. The interior is designed with both aesthetics and functionality in mind, utilizing high-quality materials that provide a luxurious feel without compromising comfort. Notably, its safety suite has been enhanced to include Toyota Safety Sense 2.5+, ensuring a range of advanced driver-assistance features come standard across all trims. However, while the Highlander excels in many areas, some drivers have raised concerns about its fuel efficiency and limited configurability for certain features, such as third-row seating and advanced options. Overall, the Highlander balances practical family needs with a touch of sophistication, making it a compelling choice for buyers prioritizing safety and comfort.
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: $18,947.00
- Good/great deal percentage: 26.8%
- User rating: 4.93 / 5
- Total listings: 142
This analysis is based on CarGurus' proprietary market data from June 23, 2026, CarGurus experts' opinions, and generative AI.
4.9 Overall rating
Filter by rating
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.
Tony T
Reviewed a 2021 Toyota Highlander on Jul 5, 2022
Love this 2021 Highlander SXE model, got all the bells and whistles. No complaints. Can’t go wrong with Toyota. Out of the 20 SUV with 5000 lbs towing, this one is top IMO.
Melissa C
Reviewed a 2021 Toyota Highlander on May 6, 2024
Toyota knocked it out of the park again with this 2021 Highlander Platinum. Luxurious quiet ride Lexus feel like. Very happy with this purchase.
Frederick and Mariah P
Reviewed a 2021 Toyota Platinum AWD on Mar 5, 2023
Absolutely love the upgraded features of this car. The panoramic sunroof is stunning, the infotainment screen is huge and easy to operate, the seats are insanely comfortable, and the ride is so smooth and surprisingly quiet on the inside. We haven’t had the car for long but we are absolutely loving it so far. We are so glad that we decided to go with the platinum trim!
2021 Toyota Highlander Trims
| Trim type | MSRP |
|---|---|
| LE FWD | $37,285 |
| LE AWD | $38,885 |
| XSE FWD | $41,680 |
| XSE AWD | $43,630 |
| Limited AWD | $45,990 |
| Platinum AWD | $49,190 |
| XLE FWD | $40,085 |
| XLE AWD | $41,685 |
2021 Toyota Highlander Price Trends
CarGurus tracks the prices of millions of used car listings every year. See how the average price of 2021 Toyota Highlander prices has changed over time.
See more price trends2021 Toyota Highlander Pricing Analysis: Chicago, IL Market Report
Pricing by Nearby Locations
Market Area: Chicago, IL
Key Insights
- Highest Prices in Kalamazoo: The average price in Kalamazoo, MI ($32,833) indicates strong demand and likely a limited supply of Highlanders in the area.
- Lowest Prices in Aurora: Conversely, Aurora, IL ($30,128) offers the most competitive pricing, suggesting a more price-sensitive market with higher inventory.
- Consistent Inventory Across Regions: Most locations around Chicago show similar inventory levels, with Palatine, IL and Aurora maintaining the highest at around 232 listings each.
City-Level Pricing
| City | Total Listings | Avg Price |
|---|---|---|
| Kalamazoo, MI | 180 | $32,833 |
| Rockford, IL | 180 | $31,656 |
| Milwaukee, WI | 185 | $31,807 |
| Janesville, WI | 176 | $31,295 |
| Palatine, IL | 228 | $30,359 |
| Aurora, IL | 232 | $30,128 |
| South Bend, IN | 177 | $30,264 |
Pricing by Trim Packages
Key Insights
- XLE AWD is the Most Common Trim: With 263 listings, the XLE AWD trim is the leader in supply, underlining its popularity among shoppers.
- Limited AWD Represents Premium Offering: This trim, priced at $45,990 MSRP, reflects the upper end of the price spectrum, featuring enhanced luxury and tech capabilities.
- Price Variation Among Trims: Base trims like the LE FWD at $37,285 MSRP provide a more accessible entry point compared to the higher-end trims.
Trim-Level Details
| Trim | Listings | MSRP | Drivetrain | Engine |
|---|---|---|---|---|
| XLE AWD | 263 | $41,685 | AWD | 3.5L 295 hp V6 |
| Limited AWD | 108 | $45,990 | AWD | 3.5L 295 hp V6 |
| XLE FWD | 63 | $40,085 | FWD | 3.5L 295 hp V6 |
| LE FWD | 42 | $37,285 | FWD | 3.5L 295 hp V6 |
| LE AWD | 64 | $38,885 | AWD | 3.5L 295 hp V6 |
| XSE AWD | 47 | $43,630 | AWD | 3.5L 295 hp V6 |
| Platinum AWD | 40 | $49,190 | AWD | 3.5L 295 hp V6 |
| Limited FWD | 25 | $44,040 | FWD | 3.5L 295 hp V6 |
Pricing Analysis by Model Year
Key Insights
- Newer Models Command Higher Prices: The 2026 Highlander shows an average price of $49,880, about 8.7% above MSRP, indicating strong demand and less depreciation compared to older models.
- Steep Depreciation for Older Models: The 2019 Highlander, down 22.4% vs MSRP, reflects larger depreciation trends as vehicles age.
- Best Value Mid-Year Models: The 2022 Highlander currently averages $33,705, showing minimal depreciation of -6.5%, making it an attractive option compared to significantly older models.
Model Year Pricing
| Model Year | Original MSRP | Avg Price | Price vs MSRP |
|---|---|---|---|
| 2026 | $45,870 | $49,880 | +8.7% |
| 2025 | $40,320 | $39,020 | -3.2% |
| 2024 | $39,270 | $38,580 | -1.8% |
| 2023 | $36,620 | $35,627 | -2.7% |
| 2022 | $35,855 | $33,705 | -6.5% |
| 2020 | $34,600 | $27,493 | -20.5% |
| 2019 | $31,830 | $24,702 | -22.4% |
| 2018 | $31,230 | $22,613 | -27.7% |
| 2017 | $30,630 | $20,159 | -34.1% |
| 2016 | $30,490 | $19,171 | -37.1% |
| 2015 | $29,765 | $17,744 | -40.5% |
These recommendations are based on CarGurus' proprietary market data from June 25, 2026, CarGurus experts' opinions, and generative AI.
FAQs
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