Used Toyota Highlander for Sale in Chicago, IL
Showing 1-20 of 351 Listings
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$25,245
$25,419
GREAT DEAL
2019 Toyota Highlander Limited Platinum
- 88,577 Miles
- Listed 104 days ago
- Frankfort, IL (27 mi away)
- $3,224 Below market value of $28,469
- iSeeCars Dealer Score
Additional info close
Used 2019 Toyota Highlander Limited Platinum for Sale
88,577 Miles
Frankfort, IL (27 mi away)
| Category | Used Cars |
| Price | $25,245 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 6-cylinder |
| Fuel Type | Gas |
| Seats | 7 Seats |
| VIN | 5TDDZRFH8KS915963 |
| Location | Frankfort, IL - 27 mi. |
| Features | bluetooth, captain's chair, child safety, navigation, backup camera |
| Mileage | 88,577 mi. |
| Transmission | Automatic |
| Exterior Color | Ooh la la rouge mica |
| Interior Color | Black |
| MPG | 22 combined |
| Drivetrain | All-wheel drive |
$7,985
GREAT DEAL
2009 Toyota Highlander Sport
- 124,861 Miles
- Listed 15 days ago
- Summit Argo, IL (9 mi away)
- $2,778 Below market value of $10,763
- iSeeCars Dealer Score
Additional info close
Used 2009 Toyota Highlander Sport for Sale
124,861 Miles
Summit Argo, IL (9 mi away)
| Category | Used Cars |
| Price | $7,985 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 6-cylinder |
| Fuel Type | Gas |
| Seats | 7 Seats |
| VIN | JTEES43A792132228 |
| Location | Summit Argo, IL - 9 mi. |
| Features | child safety, backup camera, alloy wheels, power outlet, anti-theft system |
| Mileage | 124,861 mi. |
| Transmission | Automatic |
| Exterior Color | Silver |
| Interior Color | Black |
| MPG | 19 combined |
| Drivetrain | All-wheel drive |
$15,490
GREAT DEAL
2013 Toyota Highlander Limited
- 96,714 Miles
- Listed 2 days ago
- Streamwood, IL (29 mi away)
- $1,953 Below market value of $17,443
- iSeeCars Dealer Score
Additional info close
Used 2013 Toyota Highlander Limited for Sale
96,714 Miles
Streamwood, IL (29 mi away)
| Category | Used Cars |
| Price | $15,490 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 6-cylinder |
| Fuel Type | Gas |
| Seats | 7 Seats |
| VIN | 5TDDK3EH3DS250976 |
| Location | Streamwood, IL - 29 mi. |
| Features | bluetooth, child safety, navigation, backup camera, leather upholstery |
| Mileage | 96,714 mi. |
| Transmission | Automatic |
| Exterior Color | Unknown |
| MPG | 19 combined |
| Drivetrain | All-wheel drive |
$31,990
$32,190
GREAT DEAL
2023 Toyota Highlander L
- 27,569 Miles
- Listed 84 days ago
- Streamwood, IL (29 mi away)
- $5,754 Below market value of $37,744
- iSeeCars Dealer Score
Additional info close
Used 2023 Toyota Highlander L for Sale
27,569 Miles
Streamwood, IL (29 mi away)
| Category | Used Cars |
| Price | $31,990 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 4-cylinder |
| Fuel Type | Gas |
| Seats | 8 Seats |
| VIN | 5TDKDRBH8PS039947 |
| Location | Streamwood, IL - 29 mi. |
| Features | bluetooth, child safety, backup camera, internet radio, alloy wheels |
| Mileage | 27,569 mi. |
| Transmission | Automatic |
| Exterior Color | Celestial silver metallic |
| Interior Color | Black |
| MPG | 24 combined |
| Drivetrain | All-wheel drive |
| Positives | inspected |
$8,999
GREAT DEAL
2009 Toyota Highlander Sport
- 131,825 Miles
- Listed 60 days ago
- Elmhurst, IL (15 mi away)
- $1,428 Below market value of $10,427
- iSeeCars Dealer Score
Additional info close
Used 2009 Toyota Highlander Sport for Sale
131,825 Miles
Elmhurst, IL (15 mi away)
| Category | Used Cars |
| Price | $8,999 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 6-cylinder |
| Fuel Type | Gas |
| Seats | 7 Seats |
| VIN | JTEDS43A092070960 |
| Location | Elmhurst, IL - 15 mi. |
| Features | child safety, backup camera, alloy wheels, power outlet, anti-theft system |
| Mileage | 131,825 mi. |
| Transmission | Automatic |
| Exterior Color | Gray |
| Interior Color | Black |
| MPG | 20 combined |
| Drivetrain | Front-wheel drive |
$24,995
GREAT DEAL
2021 Toyota Highlander LE
- 69,011 Miles
- Listed 18 days ago
- Palos Hills, IL (13 mi away)
- $3,978 Below market value of $28,973
- iSeeCars Dealer Score
Additional info close
Used 2021 Toyota Highlander LE for Sale
69,011 Miles
Palos Hills, IL (13 mi away)
| Category | Used Cars |
| Price | $24,995 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 6-cylinder |
| Fuel Type | Gas |
| Seats | 8 Seats |
| VIN | 5TDBZRBH2MS122870 |
| Location | Palos Hills, IL - 13 mi. |
| Features | bluetooth, child safety, backup camera, alloy wheels, satellite radio |
| Mileage | 69,011 mi. |
| Transmission | Automatic |
| Exterior Color | Midnight black metallic |
| Interior Color | Black |
| MPG | 23 combined |
| Drivetrain | All-wheel drive |
$12,995
GREAT DEAL
2015 Toyota Highlander XLE
- 155,619 Miles
- Listed 4 days ago
- Chicago, IL (5 mi away)
- $2,429 Below market value of $15,424
- iSeeCars Dealer Score
Additional info close
Used 2015 Toyota Highlander XLE for Sale
155,619 Miles
Chicago, IL (5 mi away)
| Category | Used Cars |
| Price | $12,995 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 6-cylinder |
| Fuel Type | Gas |
| Seats | 8 Seats |
| VIN | 5TDJKRFH9FS102547 |
| Location | Chicago, IL - 5 mi. |
| Features | bluetooth, child safety, navigation, backup camera, leather upholstery |
| Mileage | 155,619 mi. |
| Transmission | Automatic |
| Exterior Color | Red |
| Interior Color | Black |
| MPG | 20 combined |
| Drivetrain | All-wheel drive |
$8,795
$8,995
GREAT DEAL
2011 Toyota Highlander Limited
- 187,509 Miles
- Listed 43 days ago
- Des Plaines, IL (18 mi away)
- $1,226 Below market value of $10,021
- iSeeCars Dealer Score
Additional info close
Used 2011 Toyota Highlander Limited for Sale
187,509 Miles
Des Plaines, IL (18 mi away)
| Category | Used Cars |
| Price | $8,795 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 6-cylinder |
| Fuel Type | Gas |
| Seats | 7 Seats |
| VIN | 5TDDK3EH2BS072393 |
| Location | Des Plaines, IL - 18 mi. |
| Features | bluetooth, child safety, backup camera, leather upholstery, sunroof |
| Mileage | 187,509 mi. |
| Transmission | Automatic |
| MPG | 19 combined |
| Drivetrain | All-wheel drive |
$11,500
$11,795
GREAT DEAL
2011 Toyota Highlander SE
- 85,892 Miles
- Listed 37 days ago
- Palatine, IL (27 mi away)
- $2,560 Below market value of $14,060
- iSeeCars Dealer Score
Additional info close
Used 2011 Toyota Highlander SE for Sale
85,892 Miles
Palatine, IL (27 mi away)
| Category | Used Cars |
| Price | $11,500 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 6-cylinder |
| Fuel Type | Gas |
| Seats | 7 Seats |
| VIN | 5TDZK3EH8BS047374 |
| Location | Palatine, IL - 27 mi. |
| Features | bluetooth, child safety, backup camera, leather upholstery, sunroof |
| Mileage | 85,892 mi. |
| Transmission | Automatic |
| Exterior Color | Silver |
| Interior Color | Gray |
| MPG | 20 combined |
| Drivetrain | Front-wheel drive |
$7,500
GREAT DEAL
2009 Toyota Highlander Sport
- 166,167 Miles
- Listed 13 days ago
- Midlothian, IL (15 mi away)
- $1,759 Below market value of $9,259
- iSeeCars Dealer Score
Additional info close
Used 2009 Toyota Highlander Sport for Sale
166,167 Miles
Midlothian, IL (15 mi away)
| Category | Used Cars |
| Price | $7,500 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 6-cylinder |
| Fuel Type | Gas |
| Seats | 7 Seats |
| VIN | JTEES43A592149027 |
| Location | Midlothian, IL - 15 mi. |
| Features | child safety, backup camera, alloy wheels, power outlet, anti-theft system |
| Mileage | 166,167 mi. |
| Transmission | Automatic |
| Exterior Color | Salsa red pearl |
| MPG | 19 combined |
| Drivetrain | All-wheel drive |
$9,995
$10,795
GREAT DEAL
2010 Toyota Highlander Limited
- 127,014 Miles
- Listed 197 days ago
- Burbank, IL (9 mi away)
- $1,800 Below market value of $11,795
- iSeeCars Dealer Score
Additional info close
Used 2010 Toyota Highlander Limited for Sale
127,014 Miles
Burbank, IL (9 mi away)
| Category | Used Cars |
| Price | $9,995 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 6-cylinder |
| Fuel Type | Gas |
| Seats | 7 Seats |
| VIN | JTEYK3EH9A2102556 |
| Location | Burbank, IL - 9 mi. |
| Features | child safety, backup camera, leather upholstery, alloy wheels, satellite radio |
| Mileage | 127,014 mi. |
| Transmission | Automatic |
| Exterior Color | Magnetic gray metallic |
| MPG | 20 combined |
| Drivetrain | Front-wheel drive |
$12,977
$13,477
GREAT DEAL
2013 Toyota Highlander Limited
- 131,429 Miles
- Listed 152 days ago
- Joliet, IL (32 mi away)
- $1,653 Below market value of $14,630
- iSeeCars Dealer Score
Additional info close
Used 2013 Toyota Highlander Limited for Sale
131,429 Miles
Joliet, IL (32 mi away)
| Category | Used Cars |
| Price | $12,977 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 6-cylinder |
| Fuel Type | Gas |
| Seats | 7 Seats |
| VIN | 5TDDK3EH4DS205917 |
| Location | Joliet, IL - 32 mi. |
| Features | bluetooth, child safety, navigation, backup camera, leather upholstery |
| Mileage | 131,429 mi. |
| Transmission | Automatic |
| Exterior Color | Blue |
| Interior Color | Brown |
| MPG | 19 combined |
| Drivetrain | All-wheel drive |
$36,891
$36,941
GREAT DEAL
2024 Toyota Highlander Limited
- 47,138 Miles
- Listed 148 days ago
- Libertyville, IL (34 mi away)
- $5,880 Below market value of $42,771
- iSeeCars Dealer Score
Additional info close
Used 2024 Toyota Highlander Limited for Sale
47,138 Miles
Libertyville, IL (34 mi away)
| Category | Used Cars |
| Price | $36,891 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 4-cylinder |
| Fuel Type | Gas |
| Seats | 7 Seats |
| VIN | 5TDKDRBH6RS555338 |
| Location | Libertyville, IL - 34 mi. |
| Features | bluetooth, captain's chair, child safety, navigation, backup camera |
| Mileage | 47,138 mi. |
| Transmission | Automatic |
| Exterior Color | Silver |
| Interior Color | Black |
| MPG | 24 combined |
| Drivetrain | All-wheel drive |
$6,999
GREAT DEAL
2007 Toyota Highlander Sport
- 129,805 Miles
- Listed 29 days ago
- Midlothian, IL (15 mi away)
- $935 Below market value of $7,934
- iSeeCars Dealer Score
Additional info close
Used 2007 Toyota Highlander Sport for Sale
129,805 Miles
Midlothian, IL (15 mi away)
| Category | Used Cars |
| Price | $6,999 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 6-cylinder |
| Fuel Type | Gas |
| Seats | 7 Seats |
| VIN | JTEEP21AX70216416 |
| Location | Midlothian, IL - 15 mi. |
| Features | captain's chair, child safety, alloy wheels, power outlet |
| Mileage | 129,805 mi. |
| Transmission | Automatic |
| Exterior Color | Blue |
| Interior Color | Beige |
| MPG | 19 combined |
| Drivetrain | All-wheel drive |
$38,770
GOOD DEAL
2023 Toyota Highlander Limited
- 38,175 Miles
- Listed 21 days ago
- Saint Charles, IL (32 mi away)
- $2,102 Below market value of $40,872
- iSeeCars Dealer Score
Additional info close
Used 2023 Toyota Highlander Limited for Sale
38,175 Miles
Saint Charles, IL (32 mi away)
| Category | Certified Used Cars |
| Price | $38,770 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 4-cylinder |
| Fuel Type | Gas |
| Seats | 7 Seats |
| VIN | 5TDKDRBH4PS504675 |
| Location | Saint Charles, IL - 32 mi. |
| Features | bluetooth, captain's chair, child safety, navigation, backup camera |
| Mileage | 38,175 mi. |
| Transmission | Automatic |
| Exterior Color | Midnight black metallic |
| MPG | 24 combined |
| Drivetrain | All-wheel drive |
| Positives | certified pre-owned car, warranty, inspected, clean history |
$42,588
$42,659
GOOD DEAL
2022 Toyota Highlander Platinum
- 31,833 Miles
- Listed 18 days ago
- Matteson, IL (23 mi away)
- $2,364 Below market value of $44,952
- iSeeCars Dealer Score
Additional info close
Used 2022 Toyota Highlander Platinum for Sale
31,833 Miles
Matteson, IL (23 mi away)
| Category | Certified Used Cars |
| Price | $42,588 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 6-cylinder |
| Fuel Type | Gas |
| Seats | 7 Seats |
| VIN | 5TDFZRBHXNS197352 |
| Location | Matteson, IL - 23 mi. |
| Features | bluetooth, captain's chair, child safety, navigation, backup camera |
| Mileage | 31,833 mi. |
| Transmission | Automatic |
| Exterior Color | Ruby flare pearl |
| Interior Color | Gray |
| MPG | 23 combined |
| Drivetrain | All-wheel drive |
| Positives | certified pre-owned car, receipts, warranty, one owner, inspected |
$37,488
$37,659
GOOD DEAL
2021 Toyota Highlander Platinum
- 50,313 Miles
- Listed 22 days ago
- Matteson, IL (23 mi away)
- $1,175 Below market value of $38,663
- iSeeCars Dealer Score
Additional info close
Used 2021 Toyota Highlander Platinum for Sale
50,313 Miles
Matteson, IL (23 mi away)
| Category | Certified Used Cars |
| Price | $37,488 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 6-cylinder |
| Fuel Type | Gas |
| Seats | 7 Seats |
| VIN | 5TDFZRBH0MS079485 |
| Location | Matteson, IL - 23 mi. |
| Features | bluetooth, captain's chair, child safety, navigation, backup camera |
| Mileage | 50,313 mi. |
| Transmission | Automatic |
| Exterior Color | Ruby flare pearl |
| Interior Color | Beige |
| MPG | 23 combined |
| Drivetrain | All-wheel drive |
| Positives | certified pre-owned car, warranty, one owner, inspected, receipts |
$17,092
GOOD DEAL
2013 Toyota Highlander Limited
- 80,161 Miles
- Listed Today
- Libertyville, IL (34 mi away)
- $1,877 Below market value of $18,969
- iSeeCars Dealer Score
Additional info close
Used 2013 Toyota Highlander Limited for Sale
80,161 Miles
Libertyville, IL (34 mi away)
| Category | Used Cars |
| Price | $17,092 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 6-cylinder |
| Fuel Type | Gas |
| Seats | 7 Seats |
| VIN | 5TDDK3EH7DS221125 |
| Location | Libertyville, IL - 34 mi. |
| Features | bluetooth, child safety, navigation, backup camera, leather upholstery |
| Mileage | 80,161 mi. |
| Transmission | Automatic |
| Exterior Color | Magnetic gray metallic |
| Interior Color | Gray |
| MPG | 19 combined |
| Drivetrain | All-wheel drive |
| Positives | certified pre-owned car |
$36,990
GOOD DEAL
2021 Toyota Highlander XSE
- 21,151 Miles
- Listed 1 day ago
- Chicago, IL (10 mi away)
- $3,121 Below market value of $40,111
- iSeeCars Dealer Score
Additional info close
Used 2021 Toyota Highlander XSE for Sale
21,151 Miles
Chicago, IL (10 mi away)
| Category | Used Cars |
| Price | $36,990 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 6-cylinder |
| Fuel Type | Gas |
| Seats | 7 Seats |
| VIN | 5TDJZRBH8MS115014 |
| Location | Chicago, IL - 10 mi. |
| Features | bluetooth, captain's chair, child safety, backup camera, sunroof |
| Mileage | 21,151 mi. |
| Transmission | Automatic |
| Exterior Color | Magnetic gray metallic |
| Interior Color | Red |
| MPG | 23 combined |
| Drivetrain | All-wheel drive |
$37,490
$37,990
GREAT DEAL
2023 Toyota Highlander XLE
- 18,593 Miles
- Listed 43 days ago
- Chicago, IL (10 mi away)
- $4,291 Below market value of $41,781
- iSeeCars Dealer Score
Additional info close
Used 2023 Toyota Highlander XLE for Sale
18,593 Miles
Chicago, IL (10 mi away)
| Category | Used Cars |
| Price | $37,490 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 4-cylinder |
| Fuel Type | Gas |
| Seats | 7 Seats |
| VIN | 5TDKDRBH2PS041709 |
| Location | Chicago, IL - 10 mi. |
| Features | bluetooth, captain's chair, child safety, backup camera, internet radio |
| Mileage | 18,593 mi. |
| Transmission | Automatic |
| Exterior Color | Ruby flare pearl |
| Interior Color | Gray |
| MPG | 24 combined |
| Drivetrain | All-wheel drive |
Page 1 of 18
Used Toyota Highlander in Chicago
How to save money when buying a used Toyota Highlander in Chicago?
| Engine | A 4-Cylinder Highlander costs $4,636 less than a 6-Cylinder |
| Drive Type | A front-wheel drive (FWD) Toyota Highlander can be priced $2,211 less than an all-wheel drive (AWD) |
What colors are the best deals for a Toyota Highlander in Chicago?
Least Expensive Color
Gold
$1,850
Average Savings
Most Expensive Color
Blue
$955
Average Premium
Average car color pricing for a used Toyota Highlander in Chicago?
| Rank | Color | Compared to Avg. Price |
|---|---|---|
| Gold | $1,850 Savings | |
| Brown | $742 Savings | |
| Orange | $675 Savings | |
| Silver | $603 Savings | |
| Black | $200 Savings | |
| White | $18 Savings | |
| Red | $63 Higher | |
| Green | $191 Higher | |
| Gray | $329 Higher | |
| Blue | $955 Higher |
What Toyota Highlander color has the best resale value in Chicago?
Price differences by car color compared to the average price of a used Toyota Highlander in Chicago
What is the best time to buy a used Toyota Highlander in Chicago?
Good times to buy
$274 Average Savings
January, September, October, November, December are good times to buy to find the best prices.
Good times to sell
$198 Average Premium
February, March, April, May, June, July, August are good times to sell to get the best prices.
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Explore other cities
| Average Price | Deals | Listings | |
|---|---|---|---|
| Toyota Highlander in Indianapolis | $27,414 | Save $2,880 on 26 deals | 100 listings |
Average Price of Toyota Highlander Trims
| Trim | Average Price | Listings | Specs | ||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|
|
Toyota Highlander XLE (2014-2020) |
$29,671 | 4,895 Listings |
|
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|
Toyota Highlander Limited (2002-2020) |
$23,949 | 1,971 Listings |
|
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|
Toyota Highlander LE (2014-2020) |
$28,617 | 1,779 Listings |
|
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|
Toyota Highlander XSE (2021) |
$36,886 | 695 Listings |
|
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|
Toyota Highlander L (2020) |
$32,708 | 662 Listings |
|
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|
Toyota Highlander Platinum (2020) |
$40,051 | 618 Listings |
|
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|
Toyota Highlander SE (2010-2013, 2017-2019) |
$16,932 | 572 Listings |
|
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|
Toyota Highlander Base (2001-2013) |
$8,965 | 552 Listings |
|
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|
Toyota Highlander Limited Platinum (2014-2020) |
$23,105 | 280 Listings |
|
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|
Toyota Highlander LE Plus (2014-2019) |
$19,399 | 266 Listings |
|