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1,449 listings
- $25,998good price$1,055 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 - Price Drop$29,977fair price$571 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$590 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 - Price Drop$34,590good price$1,759 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 - $30,991fair price$878 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 - $33,867fair price$740 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$29,888fair price$547 below market
- 111,400 miles
- 7 Seats, 20 City / 27 Hwy MPG
- Chicago Auto Place (22 mi away)
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Located in Downers Grove, IL / 22 miles away from Chicago, IL
AutoCheck Vehicle History Summary Unavailable.
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDFZRBH4LS054202
Stock: H9069B
Certified Pre-Owned: No
Listed since: 08-05-2025 - New Listing$31,998fair price$368 above market
- 44,929 miles
- 7 Seats, 20 City / 27 Hwy MPG
- CarMax Hillside (Eisenhower Expy) (14 mi away)
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Located in Hillside, IL / 14 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 Unavailable.
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDGZRBH3LS054843
Stock: 27596184
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*
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: 5TDGZRBH5LS511801
Stock: 2003792730
Certified Pre-Owned: No
Listed since: 06-07-2025- $32,999great price$3,915 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 MPGClean, one-owner 2...
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 - New Listing$31,694great price$3,652 below market
- 31,212 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 20 City / 26 Hwy MPG
- Pauly Toyota (41 mi away)
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Located in Crystal Lake, IL / 41 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: 5TDDZRFH1KS980654
Stock: XX7502
Certified Pre-Owned: Yes
Listed since: 07-29-2025 - $20,981good price$1,297 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 - $22,990fair price$690 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 - Price Drop$36,995good price$1,445 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$498 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 - Price Drop$32,543good price$1,735 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$1,439 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 - $27,490fair price$548 below market
- 89,250 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- Autos of Chicago (23 mi away)
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Located in Arlington Heights, IL / 23 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:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 5TDGZRAH2MS534598
Stock: 4171
Certified Pre-Owned: No
Listed since: 07-07-2025 - $35,990fair price$517 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 - Price Drop$24,990fair price$291 below market
- 91,775 miles
- No accidents, 2 owners, corporate fleet vehicle
- 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: 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:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDJZRFH9KS566833
Stock: 2003662121
Certified Pre-Owned: No
Listed since: 05-29-2025
Showing 1 - 21 out of 1,449 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 | $24,868 | $27,244 | $29,533 |
| Clean | $24,224 | $26,530 | $28,750 |
| Average | $23,151 | $25,340 | $27,444 |
| Rough | $21,756 | $23,793 | $25,747 |
The average list price of a used 2020 Toyota Highlander in Chicago, Illinois is $29,874. The average mileage on a used Toyota Highlander 2020 for sale in Chicago, Illinois is 77,047. Based on the average mileage of 77,047 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 $23,151.
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