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1,443 listings
- $25,998good price$989 below market
- 99,924 miles
- No accidents, 1 owner, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Umansky Chevrolet (87 mi away)
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Located in Glendale, WI / 87 miles away from Chicago, IL
Command the road in this versatile and family-friendly AWD 2020 Toyota Highlander XLE, now available at Umansky Chevrolet Milwaukee. Featuring a bold ...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDGZRBH7LS048687
Stock: P48687
Certified Pre-Owned: No
Listed since: 06-19-2025 - New Listing$35,694good price$1,977 below market
- 63,226 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Gerald Toyota of Matteson (27 mi away)
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Located in Matteson, IL / 27 miles away from Chicago, IL
New Price! Recent Arrival! 2020 Toyota Highlander Platinum Midnight Black Metallic *ONE OWNER, *NAVIGATION, *BLUETOOTH, *BACKUP CAMERA, *MOONROOF, *LE...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDFZRBH4LS037223
Stock: 706079A
Certified Pre-Owned: Yes
Listed since: 07-17-2025 - Price Drop$29,977fair price$558 above market
- 67,827 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Woodfield Lexus (25 mi away)
- Home delivery*
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Located in Schaumburg, IL / 25 miles away from Chicago, IL
** Local Trade**, ** Lane Departure Warning, ** Blind Spot Monitor, ** Alloy Wheels / Premium Wheels, ** Apple CarPlay/Android Auto, ** Backup Camera,...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDGZRBH0LS039071
Stock: 251031A
Certified Pre-Owned: No
Listed since: 06-27-2025 - $29,808fair price$289 below market
- 87,357 miles
- No accidents, 1 owner, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Lexus of Orland (22 mi away)
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Located in Orland Park, IL / 22 miles away from Chicago, IL
Blizzard Pearl 2020 Toyota Highlander Limited AWD 8-Speed Automatic 3.5L V6 DOHC NAVIGATION!, LOCAL TRADE!, GREAT VEHICLE HISTORY!, PARK ASSIST, BACK ...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDDZRBH5LS003993
Stock: LX07821
Certified Pre-Owned: No
Listed since: 07-02-2025 - $30,991fair price$757 below market
- 99,422 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Romeoville Toyota (34 mi away)
- Home delivery*
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Located in Romeoville, IL / 34 miles away from Chicago, IL
2020 Toyota Highlander Platinum ***ONE OWNER*** AWD, 20 Painted Alloy Wheels, Electronic Rear-View Mirror, Heated rear seats, Heated steering wheel, H...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDFZRBH4LS037688
Stock: T18736A
Certified Pre-Owned: No
Listed since: 07-19-2025 - Price Drop$34,990fair price$1,213 below market
- 63,058 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Carvana - Chicago (41 mi away)
- Home delivery*
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Located in Chicago, IL / 41 miles away from Chicago, IL
At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts you ...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDFZRBH6LS021329
Stock: 2003788931
Certified Pre-Owned: No
Listed since: 06-06-2025 - $33,867fair price$786 above market
- 38,895 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Elgin Hyundai (31 mi away)
- Home delivery*Five Star Dealer
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Located in Bartlett, IL / 31 miles away from Chicago, IL
Recent Arrival! 2020 Toyota Highlander 4D Sport Utility XLE AWD.Odometer is 15064 miles below market average! 20/27 City/Highway MPGBUY YOUR NEXT PRE-...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDHZRBH7LS033420
Stock: H22805A
Certified Pre-Owned: No
Listed since: 07-26-2025 - New Listing$30,998fair price$1,063 above market
- 32,993 miles
- 1 accident, 1 owner, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- CarMax Merrillville (33 mi away)
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Located in Merrillville, IN / 33 miles away from Chicago, IL
CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...
AutoCheck Vehicle History Summary
Accident Free Vehicle: No
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDBZRBHXLS522299
Stock: 27227606
Certified Pre-Owned: No - New Listing
- 39,806 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Carvana - Chicago (41 mi away)
- Home delivery*
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Located in Chicago, IL / 41 miles away from Chicago, IL
At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts you ...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDDZRBH2LS052603
Stock: 2003934648
Certified Pre-Owned: No
Listed since: 08-01-2025 - 61,328 miles
- No accidents, 1 owner, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Carvana - Chicago (41 mi away)
- Home delivery*
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Located in Chicago, IL / 41 miles away from Chicago, IL
At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts you ...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDGZRBH5LS511801
Stock: 2003792730
Certified Pre-Owned: No
Listed since: 06-07-2025- $20,981good price$1,428 below market
- 138,514 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 20 City / 26 Hwy MPG
- Murgado Ford of Chicago (4 mi away)
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Located in Chicago, IL / 4 miles away from Chicago, IL
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDJZRFH0KS960110
Stock: FB07005A
Certified Pre-Owned: No
Listed since: 06-25-2025 - Price Drop$22,990good price$972 below market
- 110,269 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 26 Hwy MPG
- Carvana - Chicago (41 mi away)
- Home delivery*
Close
Located in Chicago, IL / 41 miles away from Chicago, IL
At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts you ...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDJZRFH6KS610061
Stock: 2003831711
Certified Pre-Owned: No
Listed since: 06-19-2025 - $34,497good price$2,114 below market
- 26,966 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Honda City Chicago (7 mi away)
- Home delivery*
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Located in Chicago, IL / 7 miles away from Chicago, IL
2021 Toyota Highlander XLEPriced below KBB Fair Purchase Price! Odometer is 20903 miles below market average! 20/27 City/Highway MPGStop by Honda City...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDHZRBH9MS155522
Stock: C20140A
Certified Pre-Owned: No
Listed since: 05-12-2025 - $37,980good price$773 below market
- 45,463 miles
- No accidents, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- CarWise Gurnee (39 mi away)
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Located in Gurnee, IL / 39 miles away from Chicago, IL
** Adaptive Cruise Control, ** Alloy Wheels / Premium Wheels, ** Automatic Emergency Braking, ** Backup Camera, ** Blind Spot Monitor, ** Bluetooth, H...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDFZRBH2MS159564
Stock: GG29037
Certified Pre-Owned: No
Listed since: 06-17-2025 - Price Drop$16,999fair price$492 above market
- 183,439 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- Your Choice Autos - Waukegan (34 mi away)
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Located in Waukegan, IL / 34 miles away from Chicago, IL
2019 Toyota Highlander LE 4dr SUV (3.5L V6) features: 3.5L V6 engine 8-speed automatic transmission Front-wheel drive Seating for up to 8 passengers F...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDZZRFH9KS297641
Stock: WYC-297641
Certified Pre-Owned: No
Listed since: 06-16-2025 - $32,779good price$1,512 below market
- 72,809 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Zeigler Buick GMC of Lincolnwood (9 mi away)
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Located in Lincolnwood, IL / 9 miles away from Chicago, IL
2021 Toyota Highlander XSE Midnight Black Metallic AWD*, NAVIGATION w/BACKUP CAMERA*, BLUETOOTH w/MUSIC STREAMING*, BLIND SPOT MONITOR*, PRE-COLLSION ...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDJZRBH3MS106026
Stock: M25401A
Certified Pre-Owned: No
Listed since: 05-23-2025 - Price Drop$25,377good price$1,504 below market
- 84,094 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 20 City / 26 Hwy MPG
- Antioch Chrysler Dodge Jeep Ram (47 mi away)
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Located in Antioch, IL / 47 miles away from Chicago, IL
**BLUETOOTH**, **REARVIEW CAMERA**, **AWD**, *** FULLY SERVICED & DETAILED ***, *** SHARP LOOKING SUV ***, *** ROOF RACK ***, AWD, ABS brakes, Active ...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDJZRFH6KS577756
Stock: 20849U
Certified Pre-Owned: No
Listed since: 07-11-2025 - $35,990fair price$221 below market
- 30,246 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Carvana - Chicago (41 mi away)
- Home delivery*
Close
Located in Chicago, IL / 41 miles away from Chicago, IL
At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts you ...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDGZRBH5MS160129
Stock: 2003862153
Certified Pre-Owned: No
Listed since: 07-12-2025 - $35,311good price$1,314 below market
- 62,345 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Schaumburg Toyota (27 mi away)
- Home delivery*
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Located in Schaumburg, IL / 27 miles away from Chicago, IL
** Adaptive Cruise Control, ** Alloy Wheels / Premium Wheels, ** Apple CarPlay/Android Auto, ** Automatic Emergency Braking, ** Backup Camera, ** Blin...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDJZRBH6MS148383
Stock: 251835A
Certified Pre-Owned: Yes
Listed since: 07-15-2025 - $35,100fair price$43 below market
- 73,884 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- CarWise Gurnee (39 mi away)
Close
Located in Gurnee, IL / 39 miles away from Chicago, IL
** Adaptive Cruise Control, ** Alloy Wheels / Premium Wheels, ** Automatic Emergency Braking, ** Backup Camera, ** Blind Spot Monitor, ** Bluetooth, H...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDFZRBH1MS067670
Stock: GL28864
Certified Pre-Owned: No
Listed since: 05-21-2025 - $25,950good price$895 below market
- 111,537 miles
- 1 accident, 2 owners, rental vehicle
- 7 Seats, 20 City / 27 Hwy MPG
- iDrive Motor Sports (9 mi away)
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Located in Berwyn, IL / 9 miles away from Chicago, IL
This 2021 Toyota Highlander XLE, has a Celestial Silver Metallic exterior and an Black interior color. 111537 miles. Stock Number 10268. You c...
AutoCheck Vehicle History Summary
Accident Free Vehicle: No
Personal Use Only: No
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDGZRBH3MS524726
Stock: 10268
Certified Pre-Owned: No
Listed since: 07-03-2025
Showing 1 - 21 out of 1,443 listings
Consumer Reviews for the Toyota Highlander
Read recent reviews for the Toyota Highlander
"Some Adjustment Needed"
Bill, 01/11/2020
2020 Toyota Highlander Limited 4dr SUV (3.5L 6cyl 8A)
Test drove the 2020 Limited. V-6 engine was responsive and ride was very quiet. Very good standard technology and driving safety packages. Interior had quality materials and good fit and finish. Second row captains chair seats are comfortable with plenty of room behind first row, third row seats useless except for small children which you would want in second row. Big disappointment … was drivers seat height adjustment; you better be 5'4" or above to have clear visibility over steering wheel and dash. Also, passenger seat has NO height adjustment; passengers 6'3" or above will be at or close to the ceiling. Except for the lack of adequate front seat height adjustments, I loved the car.
Used 2020 Toyota Highlander in Chicago, IL Values
Estimated values
2020 Toyota Highlander XLE 4dr SUV AWD (3.5L 6cyl 8A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $25,078 | $27,504 | $29,841 |
| Clean | $24,429 | $26,784 | $29,049 |
| Average | $23,347 | $25,582 | $27,730 |
| Rough | $21,940 | $24,021 | $26,015 |
The average list price of a used 2020 Toyota Highlander in Chicago, Illinois is $30,831. The average mileage on a used Toyota Highlander 2020 for sale in Chicago, Illinois is 75,876. Based on the average mileage of 75,876 for used 2020 Toyota Highlander for sale in Chicago, IL and using an average vehicle condition rating, which means the vehicle may have a few mechanical and/or cosmetic problems and may require a considerable amount of reconditioning, we appraise the average trade-in value of a used Toyota Highlander 2020 in Chicago, Illinois to be $23,347.
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