Used Toyota Highlander for Sale in Chicago, IL
Showing 1-20 of 370 Listings
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$10,538
$10,688
GREAT DEAL
2013 Toyota Highlander Highlander V6
- 140,645 Miles
- Downers Grove, IL (19 mi away)
- Remaining Lifespan: 5.7 yrs
- $2,011 Below market value of $12,549
- Listed 99 days ago
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Used 2013 Toyota Highlander Highlander V6 for Sale
140,645 Miles
Downers Grove, IL (19 mi away)
| Category | Used Cars |
| Price | $10,538 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 6-cylinder |
| Fuel Type | Gas |
| Seats | 7 Seats |
| VIN | 5TDZK3EH2DS117101 |
| Location | Downers Grove, IL - 19 mi. |
| Features | bluetooth, child safety, alloy wheels, power outlet |
| Mileage | 140,645 mi. |
| Transmission | Automatic |
| Exterior Color | Classic silver metallic |
| Interior Color | Gray |
| MPG | 20 combined |
| Drivetrain | Front-wheel drive |
$42,998
$43,599
GOOD DEAL
2025 Toyota Highlander Limited
- 31,126 Miles
- Chicago, IL (3 mi away)
- $3,049 Below market value of $46,047
- 1 Owner, Certified used
- Listed 22 days ago
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Used 2025 Toyota Highlander Limited for Sale
31,126 Miles
Chicago, IL (3 mi away)
| Category | Certified Used Cars |
| Price | $42,998 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 4-cylinder |
| Fuel Type | Gas |
| Seats | 7 Seats |
| VIN | 5TDKDRBH7SS575720 |
| Location | Chicago, IL - 3 mi. |
| Features | bluetooth, captain's chair, child safety, navigation, backup camera |
| Mileage | 31,126 mi. |
| Transmission | Automatic |
| Exterior Color | Wind chill pearl |
| Interior Color | Black |
| MPG | 24 combined |
| Drivetrain | All-wheel drive |
| Positives | inspected, warranty, clean history, certified pre-owned car |
$5,400
$5,895
GREAT DEAL
2005 Toyota Highlander Limited
- 162,756 Miles
- Roselle, IL (23 mi away)
- Remaining Lifespan: 5.1 yrs
- $776 Below market value of $6,176
- Listed 165 days ago
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Used 2005 Toyota Highlander Limited for Sale
162,756 Miles
Roselle, IL (23 mi away)
| Category | Used Cars |
| Price | $5,400 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 6-cylinder |
| Fuel Type | Gas |
| Seats | 7 Seats |
| VIN | JTEEP21A150131140 |
| Location | Roselle, IL - 23 mi. |
| Features | captain's chair, alloy wheels, anti-theft system |
| Mileage | 162,756 mi. |
| Transmission | Automatic |
| Exterior Color | Red |
| MPG | 19 combined |
| Drivetrain | All-wheel drive |
$26,995
GOOD DEAL
2021 Toyota Highlander LE
- 37,579 Miles
- Midlothian, IL (15 mi away)
- Remaining Lifespan: 10.4 yrs
- $2,184 Below market value of $29,179
- Listed 43 days ago
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Used 2021 Toyota Highlander LE for Sale
37,579 Miles
Midlothian, IL (15 mi away)
| Category | Used Cars |
| Price | $26,995 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 6-cylinder |
| Fuel Type | Gas |
| Seats | 8 Seats |
| VIN | 5TDBZRBHXMS119831 |
| Location | Midlothian, IL - 15 mi. |
| Features | bluetooth, child safety, backup camera, alloy wheels, satellite radio |
| Mileage | 37,579 mi. |
| Transmission | Automatic |
| Exterior Color | Silver |
| Interior Color | Black |
| MPG | 23 combined |
| Drivetrain | All-wheel drive |
$8,000
GOOD DEAL
2009 Toyota Highlander Base
- 143,627 Miles
- Arlington Heights, IL (23 mi away)
- Remaining Lifespan: 5.3 yrs
- $606 Below market value of $8,606
- Listed 11 days ago
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Used 2009 Toyota Highlander Base for Sale
143,627 Miles
Arlington Heights, IL (23 mi away)
| Category | Used Cars |
| Price | $8,000 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 4-cylinder |
| Fuel Type | Gas |
| Seats | 5 Seats |
| VIN | JTEDA41A692006671 |
| Location | Arlington Heights, IL - 23 mi. |
| Features | child safety, alloy wheels, power outlet |
| Mileage | 143,627 mi. |
| Transmission | Automatic |
| Exterior Color | Blizzard pearl |
| Interior Color | Beige |
| MPG | 22 combined |
| Drivetrain | Front-wheel drive |
$8,795
$8,995
GOOD DEAL
2011 Toyota Highlander Limited
- 197,351 Miles
- Carol Stream, IL (24 mi away)
- Remaining Lifespan: 5.5 yrs
- $633 Below market value of $9,428
- Listed 51 days ago
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Used 2011 Toyota Highlander Limited for Sale
197,351 Miles
Carol Stream, IL (24 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 | 5TDDK3EH2BS077254 |
| Location | Carol Stream, IL - 24 mi. |
| Features | bluetooth, child safety, backup camera, leather upholstery, sunroof |
| Mileage | 197,351 mi. |
| Transmission | Automatic |
| Exterior Color | Silver |
| Interior Color | Gray |
| MPG | 19 combined |
| Drivetrain | All-wheel drive |
$18,500
GOOD DEAL
2018 Toyota Highlander XLE
- 131,139 Miles
- Lansing, IL (20 mi away)
- Remaining Lifespan: 7.8 yrs
- $838 Below market value of $19,338
- Listed 8 days ago
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Used 2018 Toyota Highlander XLE for Sale
131,139 Miles
Lansing, IL (20 mi away)
| Category | Used Cars |
| Price | $18,500 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 6-cylinder |
| Fuel Type | Gas |
| Seats | 7 Seats |
| VIN | 5TDJZRFH4JS808197 |
| Location | Lansing, IL - 20 mi. |
| Features | bluetooth, captain's chair, child safety, navigation, backup camera |
| Mileage | 131,139 mi. |
| Transmission | Automatic |
| Exterior Color | Ooh la la rouge mica |
| MPG | 22 combined |
| Drivetrain | All-wheel drive |
| Positives | clean history, certified pre-owned car |
$29,790
$29,990
GOOD DEAL
2023 Toyota Highlander L
- 54,649 Miles
- Streamwood, IL (29 mi away)
- Remaining Lifespan: 11.9 yrs
- $2,939 Below market value of $32,729
- Listed 50 days ago
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Used 2023 Toyota Highlander L for Sale
54,649 Miles
Streamwood, IL (29 mi away)
| Category | Used Cars |
| Price | $29,790 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 4-cylinder |
| Fuel Type | Gas |
| Seats | 8 Seats |
| VIN | 5TDKDRBH9PS016788 |
| Location | Streamwood, IL - 29 mi. |
| Features | bluetooth, child safety, backup camera, internet radio, alloy wheels |
| Mileage | 54,649 mi. |
| Transmission | Automatic |
| Exterior Color | Magnetic gray metallic |
| Interior Color | Gray |
| MPG | 24 combined |
| Drivetrain | All-wheel drive |
$19,995
$20,995
GOOD DEAL
2016 Toyota Highlander Limited
- 94,992 Miles
- West Chicago, IL (29 mi away)
- Remaining Lifespan: 7.1 yrs
- $1,256 Below market value of $21,251
- Listed 14 days ago
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Used 2016 Toyota Highlander Limited for Sale
94,992 Miles
West Chicago, IL (29 mi away)
| Category | Used Cars |
| Price | $19,995 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 6-cylinder |
| Fuel Type | Gas |
| Seats | 7 Seats |
| VIN | 5TDDKRFHXGS258515 |
| Location | West Chicago, IL - 29 mi. |
| Features | bluetooth, captain's chair, child safety, navigation, backup camera |
| Mileage | 94,992 mi. |
| Transmission | Automatic |
| Exterior Color | Silver |
| Interior Color | Gray |
| MPG | 20 combined |
| Drivetrain | All-wheel drive |
$14,950
GOOD DEAL
2015 Toyota Highlander XLE
- 143,625 Miles
- Villa Park, IL (16 mi away)
- Remaining Lifespan: 6.8 yrs
- $722 Below market value of $15,672
- Listed 15 days ago
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Used 2015 Toyota Highlander XLE for Sale
143,625 Miles
Villa Park, IL (16 mi away)
| Category | Used Cars |
| Price | $14,950 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 6-cylinder |
| Fuel Type | Gas |
| Seats | 8 Seats |
| VIN | 5TDJKRFH8FS122854 |
| Location | Villa Park, IL - 16 mi. |
| Features | bluetooth, child safety, navigation, backup camera, leather upholstery |
| Mileage | 143,625 mi. |
| Transmission | Automatic |
| Exterior Color | Red |
| Interior Color | Black |
| MPG | 20 combined |
| Drivetrain | All-wheel drive |
$40,995
$41,399
GOOD DEAL
2023 Toyota Highlander Platinum
- 21,595 Miles
- Crystal Lake, IL (44 mi away)
- Remaining Lifespan: 11.9 yrs
- $1,554 Below market value of $42,549
- Listed 60 days ago
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Used 2023 Toyota Highlander Platinum for Sale
21,595 Miles
Crystal Lake, IL (44 mi away)
| Category | Used Cars |
| Price | $40,995 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 4-cylinder |
| Fuel Type | Gas |
| Seats | 7 Seats |
| VIN | 5TDKDRBHXPS003290 |
| Location | Crystal Lake, IL - 44 mi. |
| Features | bluetooth, captain's chair, child safety, navigation, backup camera |
| Mileage | 21,595 mi. |
| Transmission | Automatic |
| Exterior Color | Celestial silver metallic |
| Interior Color | Black |
| MPG | 24 combined |
| Drivetrain | All-wheel drive |
$26,106
$26,941
GOOD DEAL
2019 Toyota Highlander XLE
- 60,159 Miles
- Palatine, IL (27 mi away)
- Remaining Lifespan: 8.2 yrs
- $943 Below market value of $27,049
- Listed 17 days ago
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Used 2019 Toyota Highlander XLE for Sale
60,159 Miles
Palatine, IL (27 mi away)
| Category | Used Cars |
| Price | $26,106 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 6-cylinder |
| Fuel Type | Gas |
| Seats | 7 Seats |
| VIN | 5TDJZRFH9KS619546 |
| Location | Palatine, IL - 27 mi. |
| Features | bluetooth, captain's chair, child safety, navigation, backup camera |
| Mileage | 60,159 mi. |
| Transmission | Automatic |
| Exterior Color | Midnight black metallic |
| Interior Color | Black |
| MPG | 22 combined |
| Drivetrain | All-wheel drive |
$42,690
$42,991
GOOD DEAL
2022 Toyota Highlander Platinum
- 23,419 Miles
- Saint Charles, IL (32 mi away)
- Remaining Lifespan: 11.1 yrs
- $1,081 Below market value of $43,771
- Listed 46 days ago
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Used 2022 Toyota Highlander Platinum for Sale
23,419 Miles
Saint Charles, IL (32 mi away)
| Category | Used Cars |
| Price | $42,690 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 6-cylinder |
| Fuel Type | Gas |
| Seats | 7 Seats |
| VIN | 5TDFZRBH1NS222199 |
| Location | Saint Charles, IL - 32 mi. |
| Features | bluetooth, captain's chair, child safety, navigation, backup camera |
| Mileage | 23,419 mi. |
| Transmission | Automatic |
| Exterior Color | Midnight black metallic |
| MPG | 23 combined |
| Drivetrain | All-wheel drive |
| Positives | no accidents, clean history |
$20,995
$21,499
GOOD DEAL
2019 Toyota Highlander LE
- 83,538 Miles
- Glenview, IL (17 mi away)
- Remaining Lifespan: 8.2 yrs
- $767 Below market value of $21,762
- Listed 4 days ago
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Used 2019 Toyota Highlander LE for Sale
83,538 Miles
Glenview, IL (17 mi away)
| Category | Used Cars |
| Price | $20,995 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 6-cylinder |
| Fuel Type | Gas |
| Seats | 8 Seats |
| VIN | 5TDBZRFH8KS998690 |
| Location | Glenview, IL - 17 mi. |
| Features | bluetooth, child safety, backup camera, alloy wheels, voice recognition |
| Mileage | 83,538 mi. |
| Transmission | Automatic |
| MPG | 23 combined |
| Drivetrain | All-wheel drive |
$31,900
$32,990
GOOD DEAL
2022 Toyota Highlander Limited
- 75,089 Miles
- Lockport, IL (26 mi away)
- Remaining Lifespan: 11.1 yrs
- $1,224 Below market value of $33,124
- Listed 20 days ago
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Used 2022 Toyota Highlander Limited for Sale
75,089 Miles
Lockport, IL (26 mi away)
| Category | Used Cars |
| Price | $31,900 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 6-cylinder |
| Fuel Type | Gas |
| Seats | 7 Seats |
| VIN | 5TDDZRBH7NS176661 |
| Location | Lockport, IL - 26 mi. |
| Features | bluetooth, captain's chair, child safety, navigation, backup camera |
| Mileage | 75,089 mi. |
| Transmission | Automatic |
| Exterior Color | Gray |
| Interior Color | Black |
| MPG | 23 combined |
| Drivetrain | All-wheel drive |
$19,997
GOOD DEAL
2016 Toyota Highlander XLE
- 93,235 Miles
- Bensenville, IL (16 mi away)
- Remaining Lifespan: 7.1 yrs
- $476 Below market value of $20,473
- Listed 17 days ago
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Used 2016 Toyota Highlander XLE for Sale
93,235 Miles
Bensenville, IL (16 mi away)
| Category | Used Cars |
| Price | $19,997 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 6-cylinder |
| Fuel Type | Gas |
| Seats | 8 Seats |
| VIN | 5TDJKRFH8GS255924 |
| Location | Bensenville, IL - 16 mi. |
| Features | bluetooth, child safety, navigation, backup camera, leather upholstery |
| Mileage | 93,235 mi. |
| Transmission | Automatic |
| Exterior Color | Black |
| Interior Color | Black |
| MPG | 20 combined |
| Drivetrain | All-wheel drive |
$34,790
$34,990
GOOD DEAL
2023 Toyota Highlander XLE
- 40,961 Miles
- Streamwood, IL (29 mi away)
- Remaining Lifespan: 11.9 yrs
- $1,300 Below market value of $36,090
- Listed 48 days ago
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Used 2023 Toyota Highlander XLE for Sale
40,961 Miles
Streamwood, IL (29 mi away)
| Category | Used Cars |
| Price | $34,790 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 4-cylinder |
| Fuel Type | Gas |
| Seats | 7 Seats |
| VIN | 5TDKDRBH4PS013605 |
| Location | Streamwood, IL - 29 mi. |
| Features | bluetooth, captain's chair, child safety, backup camera, internet radio |
| Mileage | 40,961 mi. |
| Transmission | Automatic |
| Exterior Color | Midnight black metallic |
| Interior Color | Black |
| MPG | 24 combined |
| Drivetrain | All-wheel drive |
$22,995
GOOD DEAL
2017 Toyota Highlander Limited Platinum
- 92,524 Miles
- Northbrook, IL (21 mi away)
- Remaining Lifespan: 7.4 yrs
- $588 Below market value of $23,583
- Listed 2 days ago
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Used 2017 Toyota Highlander Limited Platinum for Sale
92,524 Miles
Northbrook, IL (21 mi away)
| Category | Used Cars |
| Price | $22,995 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 6-cylinder |
| Fuel Type | Gas |
| Seats | 7 Seats |
| VIN | 5TDDZRFH7HS417939 |
| Location | Northbrook, IL - 21 mi. |
| Features | bluetooth, captain's chair, child safety, navigation, backup camera |
| Mileage | 92,524 mi. |
| Transmission | Automatic |
| Exterior Color | Red |
| Interior Color | Black |
| MPG | 22 combined |
| Drivetrain | All-wheel drive |
$20,556
GOOD DEAL
2018 Toyota Highlander LE
- 67,522 Miles
- Niles, IL (13 mi away)
- Remaining Lifespan: 7.8 yrs
- $1,525 Below market value of $22,081
- Listed 8 days ago
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Used 2018 Toyota Highlander LE for Sale
67,522 Miles
Niles, IL (13 mi away)
| Category | Used Cars |
| Price | $20,556 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 6-cylinder |
| Fuel Type | Gas |
| Seats | 8 Seats |
| VIN | 5TDBZRFH6JS889546 |
| Location | Niles, IL - 13 mi. |
| Features | bluetooth, child safety, backup camera, alloy wheels, voice recognition |
| Mileage | 67,522 mi. |
| Transmission | Automatic |
| Exterior Color | Silver |
| MPG | 22 combined |
| Drivetrain | All-wheel drive |
$6,995
$7,295
GOOD DEAL
2005 Toyota Highlander Base
- 120,511 Miles
- Lombard, IL (18 mi away)
- Remaining Lifespan: 5.1 yrs
- $723 Below market value of $7,718
- Listed 79 days ago
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Used 2005 Toyota Highlander Base for Sale
120,511 Miles
Lombard, IL (18 mi away)
| Category | Used Cars |
| Price | $6,995 |
| For Sale By | dealer |
| iSeeCars Dealer Score | |
| Engine | 6-cylinder |
| Fuel Type | Gas |
| Seats | 7 Seats |
| VIN | JTEDP21A550089325 |
| Location | Lombard, IL - 18 mi. |
| Features | captain's chair |
| Mileage | 120,511 mi. |
| Transmission | Automatic |
| Exterior Color | Silver |
| Interior Color | Gray |
| MPG | 19 combined |
| Drivetrain | Front-wheel drive |
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Used Cars for Sale Insights
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.
Average Price of Toyota Highlander Trims
| Trim | Average Price | Listings | Specs | ||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|
|
Toyota Highlander XLE (2014-2020) |
$29,246 | 4,702 Listings |
|
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Toyota Highlander Limited (2002-2020) |
$23,133 | 2,053 Listings |
|
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Toyota Highlander LE (2014-2020) |
$29,130 | 2,043 Listings |
|
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Toyota Highlander XSE (2021) |
$37,461 | 787 Listings |
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Toyota Highlander Platinum (2020) |
$39,914 | 733 Listings |
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|
Toyota Highlander Base (2001-2013) |
$8,440 | 557 Listings |
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Toyota Highlander SE (2010-2013, 2017-2019) |
$16,782 | 557 Listings |
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Toyota Highlander L (2020) |
$30,519 | 384 Listings |
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Toyota Highlander Limited Platinum (2014-2020) |
$22,598 | 368 Listings |
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Toyota Highlander LE Plus (2014-2019) |
$18,903 | 311 Listings |
|