Used Toyota Highlander for Sale in Chicago, IL
Showing 1-20 of 460 Listings
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$5,003
GREAT DEAL
2006 Toyota Highlander Sport
- 137,716 Miles
- Listed 15 days ago
- Elgin, IL (36 mi away)
- $2,557 Below market value of $7,560
- iSeeCars Dealer Score
Additional info close
Used 2006 Toyota Highlander Sport for Sale
137,716 Miles
Elgin, IL (36 mi away)
| Category | Used Cars |
| Price | $5,003 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 6-cylinder |
| Fuel Type | Gas |
| Seats | 7 Seats |
| VIN | JTEEP21A960153503 |
| Location | Elgin, IL - 36 mi. |
| Features | captain's chair, child safety, alloy wheels, power outlet, anti-theft system |
| Mileage | 137,716 mi. |
| Transmission | Automatic |
| Exterior Color | Unknown |
| MPG | 19 combined |
| Drivetrain | All-wheel drive |
$5,450
$6,950
GREAT DEAL
2011 Toyota Highlander SE
- 243,732 Miles
- Listed 8 days ago
- Addison, IL (19 mi away)
- $1,359 Below market value of $6,809
- iSeeCars Dealer Score
Additional info close
Used 2011 Toyota Highlander SE for Sale
243,732 Miles
Addison, IL (19 mi away)
| Category | Used Cars |
| Price | $5,450 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 6-cylinder |
| Fuel Type | Gas |
| Seats | 7 Seats |
| VIN | 5TDBK3EH3BS088027 |
| Location | Addison, IL - 19 mi. |
| Features | bluetooth, child safety, backup camera, leather upholstery, sunroof |
| Mileage | 243,732 mi. |
| Transmission | Automatic |
| Exterior Color | Magnetic gray metallic |
| Interior Color | Black |
| MPG | 19 combined |
| Drivetrain | All-wheel drive |
$17,700
$18,000
GREAT DEAL
2017 Toyota Highlander XLE
- 115,569 Miles
- Listed 34 days ago
- Lansing, IL (20 mi away)
- $3,587 Below market value of $21,287
- iSeeCars Dealer Score
Additional info close
Used 2017 Toyota Highlander XLE for Sale
115,569 Miles
Lansing, IL (20 mi away)
| Category | Used Cars |
| Price | $17,700 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 6-cylinder |
| Fuel Type | Gas |
| Seats | 7 Seats |
| VIN | 5TDJZRFH7HS429527 |
| Location | Lansing, IL - 20 mi. |
| Features | bluetooth, captain's chair, child safety, navigation, backup camera |
| Mileage | 115,569 mi. |
| Transmission | Automatic |
| Exterior Color | Ooh la la rouge mica |
| Interior Color | Black |
| MPG | 22 combined |
| Drivetrain | All-wheel drive |
$6,150
$6,350
GREAT DEAL
2007 Toyota Highlander Base
- 127,347 Miles
- Listed 99 days ago
- Addison, IL (19 mi away)
- $1,771 Below market value of $7,921
- iSeeCars Dealer Score
Additional info close
Used 2007 Toyota Highlander Base for Sale
127,347 Miles
Addison, IL (19 mi away)
| Category | Used Cars |
| Price | $6,150 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 6-cylinder |
| Fuel Type | Gas |
| Seats | 7 Seats |
| VIN | JTEEP21A170194029 |
| Location | Addison, IL - 19 mi. |
| Features | captain's chair, child safety, power outlet |
| Mileage | 127,347 mi. |
| Transmission | Automatic |
| Exterior Color | Indigo ink pearl |
| MPG | 19 combined |
| Drivetrain | All-wheel drive |
$4,675
$4,750
GREAT DEAL
2006 Toyota Highlander Base
- 168,288 Miles
- Listed 31 days ago
- Downers Grove, IL (19 mi away)
- $1,661 Below market value of $6,336
- iSeeCars Dealer Score
Additional info close
Used 2006 Toyota Highlander Base for Sale
168,288 Miles
Downers Grove, IL (19 mi away)
| Category | Used Cars |
| Price | $4,675 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 4-cylinder |
| Fuel Type | Gas |
| Seats | 5 Seats |
| VIN | JTEGD21A160138432 |
| Location | Downers Grove, IL - 19 mi. |
| Features | captain's chair, child safety, power outlet, anti-theft system |
| Mileage | 168,288 mi. |
| Transmission | Automatic |
| Exterior Color | Silver |
| Interior Color | Gray |
| MPG | 22 combined |
| Drivetrain | Front-wheel drive |
$14,450
$15,450
GREAT DEAL
2015 Toyota Highlander Limited
- 148,504 Miles
- Listed 96 days ago
- Addison, IL (19 mi away)
- $2,518 Below market value of $16,968
- iSeeCars Dealer Score
Additional info close
Used 2015 Toyota Highlander Limited for Sale
148,504 Miles
Addison, IL (19 mi away)
| Category | Used Cars |
| Price | $14,450 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 6-cylinder |
| Fuel Type | Gas |
| Seats | 7 Seats |
| VIN | 5TDDKRFH8FS091232 |
| Location | Addison, IL - 19 mi. |
| Features | bluetooth, captain's chair, child safety, navigation, backup camera |
| Mileage | 148,504 mi. |
| Transmission | Automatic |
| Exterior Color | Silver sky metallic |
| MPG | 20 combined |
| Drivetrain | All-wheel drive |
| Positives | certified pre-owned car, new tires |
$14,799
$14,999
GREAT DEAL
2013 Toyota Highlander Limited
- 109,299 Miles
- Listed 90 days ago
- Chicago, IL (3 mi away)
- $1,741 Below market value of $16,540
- iSeeCars Dealer Score
Additional info close
Used 2013 Toyota Highlander Limited for Sale
109,299 Miles
Chicago, IL (3 mi away)
| Category | Used Cars |
| Price | $14,799 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 6-cylinder |
| Fuel Type | Gas |
| Seats | 7 Seats |
| VIN | 5TDDK3EH1DS188297 |
| Location | Chicago, IL - 3 mi. |
| Features | bluetooth, child safety, navigation, backup camera, leather upholstery |
| Mileage | 109,299 mi. |
| Transmission | Automatic |
| Exterior Color | Classic silver metallic |
| Interior Color | Black |
| MPG | 19 combined |
| Drivetrain | All-wheel drive |
| Positives | receipts |
$7,494
GREAT DEAL
2006 Toyota Highlander Base
- 104,926 Miles
- Listed 7 days ago
- Chesterton, IN (35 mi away)
- $1,476 Below market value of $8,970
Additional info close
Used 2006 Toyota Highlander Base for Sale
104,926 Miles
Chesterton, IN (35 mi away)
| Category | Used Cars |
| Price | $7,494 |
| For Sale By | dealer |
| Engine | 6-cylinder |
| Fuel Type | Gas |
| Seats | 7 Seats |
| VIN | JTEEP21A160151826 |
| Location | Chesterton, IN - 35 mi. |
| Features | captain's chair, child safety, power outlet, anti-theft system |
| Mileage | 104,926 mi. |
| Transmission | Automatic |
| Exterior Color | Tan |
| MPG | 19 combined |
| Drivetrain | All-wheel drive |
$3,500
GREAT DEAL
2003 Toyota Highlander Limited
- 223,377 Miles
- Listed 15 days ago
- Midlothian, IL (15 mi away)
- $1,201 Below market value of $4,701
- iSeeCars Dealer Score
Additional info close
Used 2003 Toyota Highlander Limited for Sale
223,377 Miles
Midlothian, IL (15 mi away)
| Category | Used Cars |
| Price | $3,500 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 6-cylinder |
| Fuel Type | Gas |
| Seats | 5 Seats |
| VIN | JTEHF21A130104601 |
| Location | Midlothian, IL - 15 mi. |
| Features | captain's chair, alloy wheels, anti-theft system |
| Mileage | 223,377 mi. |
| Transmission | Automatic |
| Exterior Color | Millennium silver metallic |
| MPG | 18 combined |
| Drivetrain | All-wheel drive |
$8,789
$8,999
GREAT DEAL
2010 Toyota Highlander Base
- 133,556 Miles
- Listed 100 days ago
- Elmhurst, IL (15 mi away)
- $1,134 Below market value of $9,923
- iSeeCars Dealer Score
Additional info close
Used 2010 Toyota Highlander Base for Sale
133,556 Miles
Elmhurst, IL (15 mi away)
| Category | Used Cars |
| Price | $8,789 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 6-cylinder |
| Fuel Type | Gas |
| Seats | 7 Seats |
| VIN | 5TDBK3EH6AS027091 |
| Location | Elmhurst, IL - 15 mi. |
| Features | child safety, alloy wheels, power outlet |
| Mileage | 133,556 mi. |
| Transmission | Automatic |
| Exterior Color | Gray |
| Interior Color | Gray |
| MPG | 19 combined |
| Drivetrain | All-wheel drive |
$37,500
GOOD DEAL
2022 Toyota Highlander XSE
- 45,850 Miles
- Listed 29 days ago
- Schaumburg, IL (24 mi away)
- $1,402 Below market value of $38,902
- iSeeCars Dealer Score
Additional info close
Used 2022 Toyota Highlander XSE for Sale
45,850 Miles
Schaumburg, IL (24 mi away)
| Category | Used Cars |
| Price | $37,500 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 6-cylinder |
| Fuel Type | Gas |
| Seats | 7 Seats |
| VIN | 5TDLZRBHXNS235438 |
| Location | Schaumburg, IL - 24 mi. |
| Features | bluetooth, captain's chair, child safety, backup camera, sunroof |
| Mileage | 45,850 mi. |
| Transmission | Automatic |
| Exterior Color | Celestial silver metallic |
| Interior Color | Red |
| MPG | 23 combined |
| Drivetrain | All-wheel drive |
$13,449
$13,995
GOOD DEAL
2015 Toyota Highlander Limited
- 185,007 Miles
- Listed 12 days ago
- Libertyville, IL (34 mi away)
- $1,371 Below market value of $14,820
- iSeeCars Dealer Score
Additional info close
Used 2015 Toyota Highlander Limited for Sale
185,007 Miles
Libertyville, IL (34 mi away)
| Category | Used Cars |
| Price | $13,449 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 6-cylinder |
| Fuel Type | Gas |
| Seats | 7 Seats |
| VIN | 5TDDKRFH4FS168582 |
| Location | Libertyville, IL - 34 mi. |
| Features | bluetooth, captain's chair, child safety, navigation, backup camera |
| Mileage | 185,007 mi. |
| Transmission | Automatic |
| Exterior Color | Alumina jade metallic |
| MPG | 20 combined |
| Drivetrain | All-wheel drive |
$16,988
GREAT DEAL
2015 Toyota Highlander LE Plus
- 89,356 Miles
- Listed Today
- Berwyn, IL (7 mi away)
- $1,951 Below market value of $18,939
- iSeeCars Dealer Score
Additional info close
Used 2015 Toyota Highlander LE Plus for Sale
89,356 Miles
Berwyn, IL (7 mi away)
| Category | Used Cars |
| Price | $16,988 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 6-cylinder |
| Fuel Type | Gas |
| Seats | 8 Seats |
| VIN | 5TDBKRFH9FS119546 |
| Location | Berwyn, IL - 7 mi. |
| Features | bluetooth, child safety, navigation, backup camera, alloy wheels |
| Mileage | 89,356 mi. |
| Transmission | Automatic |
| Exterior Color | Ooh la la rouge mica |
| Interior Color | Black |
| MPG | 20 combined |
| Drivetrain | All-wheel drive |
$23,250
$23,500
GOOD DEAL
2018 Toyota Highlander XLE
- 84,883 Miles
- Listed 50 days ago
- Libertyville, IL (34 mi away)
- $1,821 Below market value of $25,071
- iSeeCars Dealer Score
Additional info close
Used 2018 Toyota Highlander XLE for Sale
84,883 Miles
Libertyville, IL (34 mi away)
| Category | Used Cars |
| Price | $23,250 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 6-cylinder |
| Fuel Type | Gas |
| Seats | 7 Seats |
| VIN | 5TDJZRFH1JS877526 |
| Location | Libertyville, IL - 34 mi. |
| Features | bluetooth, captain's chair, child safety, navigation, backup camera |
| Mileage | 84,883 mi. |
| Transmission | Automatic |
| Exterior Color | Celestial silver metallic |
| MPG | 22 combined |
| Drivetrain | All-wheel drive |
| Positives | inspected |
$40,000
$40,200
GOOD DEAL
2024 Toyota Highlander XLE
- 17,699 Miles
- Listed 99 days ago
- Frankfort, IL (27 mi away)
- $2,994 Below market value of $42,994
- iSeeCars Dealer Score
Additional info close
Used 2024 Toyota Highlander XLE for Sale
17,699 Miles
Frankfort, IL (27 mi away)
| Category | Used Cars |
| Price | $40,000 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 4-cylinder |
| Fuel Type | Gas |
| Seats | 7 Seats |
| VIN | 5TDKDRBH9RS531051 |
| Location | Frankfort, IL - 27 mi. |
| Features | bluetooth, captain's chair, child safety, backup camera, internet radio |
| Mileage | 17,699 mi. |
| Transmission | Automatic |
| Exterior Color | Midnight black metallic |
| Interior Color | Black |
| MPG | 24 combined |
| Drivetrain | All-wheel drive |
$33,990
$34,490
GOOD DEAL
2021 Toyota Highlander XLE
- 29,008 Miles
- Listed 58 days ago
- Chicago, IL (10 mi away)
- $2,039 Below market value of $36,029
- iSeeCars Dealer Score
Additional info close
Used 2021 Toyota Highlander XLE for Sale
29,008 Miles
Chicago, IL (10 mi away)
| Category | Used Cars |
| Price | $33,990 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 6-cylinder |
| Fuel Type | Gas |
| Seats | 7 Seats |
| VIN | 5TDHZRBH9MS154533 |
| Location | Chicago, IL - 10 mi. |
| Features | bluetooth, captain's chair, child safety, backup camera, sunroof |
| Mileage | 29,008 mi. |
| Transmission | Automatic |
| Exterior Color | Midnight black metallic |
| Interior Color | Black |
| MPG | 23 combined |
| Drivetrain | All-wheel drive |
| Positives | no accidents, one owner |
$13,506
$13,606
GOOD DEAL
2015 Toyota Highlander LE
- 133,602 Miles
- Listed 80 days ago
- Merrillville, IN (29 mi away)
- $1,266 Below market value of $14,772
- iSeeCars Dealer Score
Additional info close
Used 2015 Toyota Highlander LE for Sale
133,602 Miles
Merrillville, IN (29 mi away)
| Category | Used Cars |
| Price | $13,506 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 4-cylinder |
| Fuel Type | Gas |
| Seats | 8 Seats |
| VIN | 5TDZARFH4FS015242 |
| Location | Merrillville, IN - 29 mi. |
| Features | bluetooth, child safety, backup camera, alloy wheels, voice recognition |
| Mileage | 133,602 mi. |
| Transmission | Automatic |
| Exterior Color | Ooh la la rouge mica |
| Interior Color | Black |
| MPG | 22 combined |
| Drivetrain | Front-wheel drive |
| Positives | inspected, warranty, routine maintenance, certified pre-owned car |
$37,499
$38,852
GOOD DEAL
2022 Toyota Highlander XSE
- 32,539 Miles
- Listed 23 days ago
- Chesterton, IN (35 mi away)
- $3,109 Below market value of $40,608
- 1 Owner, Low annual miles
Additional info close
Used 2022 Toyota Highlander XSE for Sale
32,539 Miles
Chesterton, IN (35 mi away)
| Category | Used Cars |
| Price | $37,499 |
| For Sale By | dealer |
| Engine | 6-cylinder |
| Fuel Type | Gas |
| Seats | 7 Seats |
| VIN | 5TDLZRBHXNS216761 |
| Location | Chesterton, IN - 35 mi. |
| Features | bluetooth, captain's chair, child safety, backup camera, sunroof |
| Mileage | 32,539 mi. |
| Transmission | Automatic |
| Exterior Color | White |
| Interior Color | Black |
| MPG | 23 combined |
| Drivetrain | All-wheel drive |
| Positives | negotiable, clean history |
$32,750
$32,990
GOOD DEAL
2021 Toyota Highlander XLE
- 44,848 Miles
- Listed 36 days ago
- Libertyville, IL (34 mi away)
- $1,199 Below market value of $33,949
- iSeeCars Dealer Score
Additional info close
Used 2021 Toyota Highlander XLE for Sale
44,848 Miles
Libertyville, IL (34 mi away)
| Category | Used Cars |
| Price | $32,750 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 6-cylinder |
| Fuel Type | Gas |
| Seats | 7 Seats |
| VIN | 5TDHZRBH5MS124655 |
| Location | Libertyville, IL - 34 mi. |
| Features | bluetooth, captain's chair, child safety, backup camera, sunroof |
| Mileage | 44,848 mi. |
| Transmission | Automatic |
| Exterior Color | Moon dust |
| Interior Color | Gray |
| MPG | 23 combined |
| Drivetrain | All-wheel drive |
| Positives | inspected, clean history, certified pre-owned car |
$31,188
$31,295
GOOD DEAL
2020 Toyota Highlander XLE
- 54,237 Miles
- Listed 13 days ago
- Lisle, IL (22 mi away)
- $1,025 Below market value of $32,213
- iSeeCars Dealer Score
Additional info close
Used 2020 Toyota Highlander XLE for Sale
54,237 Miles
Lisle, IL (22 mi away)
| Category | Used Cars |
| Price | $31,188 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 6-cylinder |
| Fuel Type | Gas |
| Seats | 7 Seats |
| VIN | 5TDHZRBH9LS041440 |
| Location | Lisle, IL - 22 mi. |
| Features | bluetooth, captain's chair, child safety, backup camera, sunroof |
| Mileage | 54,237 mi. |
| Transmission | Automatic |
| Exterior Color | Midnight black metallic |
| Interior Color | Gray |
| MPG | 23 combined |
| Drivetrain | All-wheel drive |
| Positives | clean history, non-smoker, one owner |
Page 1 of 23
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 | $27,040 | Save $7,244 on 28 deals | 117 listings |
Average Price of Toyota Highlander Trims
| Trim | Average Price | Listings | Specs | ||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|
|
Toyota Highlander XLE (2014-2020) |
$30,464 | 4,337 Listings |
|
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|
Toyota Highlander Limited (2002-2020) |
$23,424 | 1,713 Listings |
|
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|
Toyota Highlander LE (2014-2020) |
$28,503 | 1,407 Listings |
|
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|
Toyota Highlander XSE (2021) |
$38,377 | 662 Listings |
|
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|
Toyota Highlander L (2020) |
$33,389 | 640 Listings |
|
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|
Toyota Highlander Base (2001-2013) |
$8,924 | 530 Listings |
|
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|
Toyota Highlander Platinum (2020) |
$40,928 | 518 Listings |
|
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|
Toyota Highlander SE (2010-2013, 2017-2019) |
$16,704 | 470 Listings |
|
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|
Toyota Highlander LE Plus (2014-2019) |
$19,327 | 252 Listings |
|
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|
Toyota Highlander Limited Platinum (2014-2020) |
$24,392 | 196 Listings |
|