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1,166 listings
- $28,700great price$5,001 below market
- 52,740 miles
- 2 accidents, 1 owner, rental vehicle
- 6cyl automatic
- Kingdom Chevrolet (8 mi away)
- Home delivery*
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Located in Chicago, IL / 8 miles away from Chicago, IL
Priced below KBB Fair Purchase Price! CARFAX One-Owner. 2021 4D Sport Utility Toyota Highlander XLE Black 8-Speed Automatic AWD 3.5L V6 DOHC HUGE INVE...
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: 5TDGZRBH5MS549112
Stock: P24490
Certified Pre-Owned: No
Listed since: 12-04-2024 - Price Drop$35,899good price$866 below market
- 86,939 miles
- No accidents, 1 owner, personal use only
- 6cyl automatic
- 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! 2021 Toyota Highlander Platinum AWD Moon Dust *ONE OWNER, *NAVIGATION, *BLUETOOTH, *BACKUP CAMERA, *3RD ROW SEATING, *AWD, ...
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: 5TDFZRBH4MS097083
Stock: 705887A
Certified Pre-Owned: Yes
Listed since: 04-15-2025 - $38,937good price$1,132 below market
- 44,849 miles
- No accidents, 1 owner, personal use only
- 6cyl automatic
- Lochmandy Buick GMC (85 mi away)
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Located in Elkhart, IN / 85 miles away from Chicago, IL
The 2021 Toyota Highlander Platinum is a luxurious and spacious midsize SUV designed for families and adventurers alike. Powered by a 3.5-liter V6 e...
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: 5TDFZRBH6MS158840
Stock: 42684A
Certified Pre-Owned: No
Listed since: 03-26-2025 - $37,617fair price$8 above market
- 43,246 miles
- No accidents, 1 owner, personal use
- 6cyl automatic
- Gerald Toyota of Matteson (27 mi away)
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Located in Matteson, IL / 27 miles away from Chicago, IL
New Price! 2021 Toyota Highlander Limited AWD Blizzard Pearl *ONE OWNER, *BLUETOOTH, *BACKUP CAMERA, *MOONROOF, *LEATHER, *3RD ROW SEATING, *AWD, Navi...
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: 5TDDZRBH4MS072451
Stock: P402995
Certified Pre-Owned: No
Listed since: 03-05-2025 - 26,830 miles
- No accidents, 1 owner, personal use
- 6cyl automatic
- Orland Toyota (22 mi away)
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Located in Tinley Park, IL / 22 miles away from Chicago, IL
2021 Toyota Highlander LE **LIKE NEW, **TOYOTA CERTIFIED, **BLACK BEAUTY, **MILES ONLY 26830, **1 OWNER CLEAN CARFAX, **BLUETOOTH, **CLOTH SEATS, **RE...
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: 5TDBZRBH2MS153018
Stock: P9858
Certified Pre-Owned: Yes
Listed since: 03-13-2025- $32,900fair price$39 above market
- 72,547 miles
- No accidents, 1 owner, personal use only
- 6cyl automatic
- Bredemann Toyota (15 mi away)
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Located in Park Ridge, IL / 15 miles away from Chicago, IL
Bredemann Toyota is the #1 Volume Toyota Dealer in IL for 2024! A Toyota Dealer since 1976, we take great pride in our dedication to providing the hig...
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: Yes
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDGZRBH0MS544724
Stock: TP7576
Certified Pre-Owned: Yes
Listed since: 06-18-2024 - Price Drop$37,897fair price$725 above market
- 44,448 miles
- No accidents, 1 owner, personal use only
- 6cyl automatic
- Lexus of Orland (22 mi away)
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Located in Orland Park, IL / 22 miles away from Chicago, IL
2021 Toyota Highlander XSE AWD 8-Speed Automatic 3.5L V6 DOHC NAVIGATION!, LOCAL TRADE!, ONE OWNER!, GREAT VEHICLE HISTORY!, PARK ASSIST, BACK UP CAME...
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: 5TDJZRBH3MS056972
Stock: LX05851
Certified Pre-Owned: No
Listed since: 04-18-2025 - Price Drop$34,590good price$586 below market
- 62,505 miles
- No accidents, 2 owners, personal use only
- 6cyl automatic
- 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: 5TDDZRBH2MS065675
Stock: 2003590378
Certified Pre-Owned: No
Listed since: 03-24-2025 - 17,802 miles
- No accidents, 2 owners, personal use only
- 6cyl automatic
- Orland Toyota (22 mi away)
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Located in Tinley Park, IL / 22 miles away from Chicago, IL
2021 Toyota Highlander Platinum **LIKE BRAND NEW, **LOCAL TRADE, **TOYOTA CERTIFIED, **MILES ONLY 17802, **CLEAN CARFAX, **NAVIGATION, **BLUETOOTH, **...
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: 5TDFZRBH5MS119074
Stock: 455751
Certified Pre-Owned: Yes
Listed since: 04-04-2025- New Listing$33,945fair price$203 above market
- 47,168 miles
- 6cyl automatic
- Grand Subaru (16 mi away)
- Home delivery*
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Located in Bensenville, IL / 16 miles away from Chicago, IL
AutoCheck Vehicle History Summary Unavailable.
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDGZRBH8MS101687
Stock: 250198A
Certified Pre-Owned: No
Listed since: 04-24-2025 - Price Drop
- 75,679 miles
- No accidents, 2 owners, rental vehicle
- 6cyl automatic
- Gerald Honda of Matteson (27 mi away)
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Located in Matteson, IL / 27 miles away from Chicago, IL
New Price! Recent Arrival! 2021 Toyota Highlander XLE AWD Blizzard Pearl * LIFETIME WARRANTY, * CLEAN CARFAX, *BLUETOOTH, *REAR VIEW CAMERA, *SUNROOF/...
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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDGZRBH5MS113621
Stock: 506719A
Certified Pre-Owned: No
Listed since: 04-13-2025 - New Listing
- 33,845 miles
- No accidents, 1 owner, personal use
- 6cyl automatic
- Fields Lexus Glenview (17 mi away)
- Home delivery*
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Located in Glenview, IL / 17 miles away from Chicago, IL
Lexus Glenview is honored to offer this GORGEOUS, one-owner, clean CARFAX, 2021 Toyota Highlander XLE in Celestial Silver Metallic with Black SofTex i...
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: 5TDGZRBH1MS528080
Stock: L25737A
Certified Pre-Owned: No
Listed since: 04-18-2025 - Not provided
- No accidents, 1 owner, personal use only
- 6cyl automatic
- Orland Toyota (22 mi away)
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Located in Tinley Park, IL / 22 miles away from Chicago, IL
2021 Toyota Highlander Limited
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: 5TDDZRBH5MS524567
Stock: 41364
Certified Pre-Owned: No
Listed since: 12-14-2020- Not Priced
- 63,354 miles
- No accidents, 1 owner, corporate fleet vehicle
- 6cyl automatic
- Orland Toyota (22 mi away)
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Located in Tinley Park, IL / 22 miles away from Chicago, IL
2021 Toyota Highlander XLE
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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDGZRBH9MS114271
Stock: P9914
Certified Pre-Owned: No
Listed since: 04-24-2025 - Not Priced
- 65,448 miles
- No accidents, 2 owners, personal use
- 6cyl automatic
- Orland Toyota (22 mi away)
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Located in Tinley Park, IL / 22 miles away from Chicago, IL
2021 Toyota Highlander XLE
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: 5TDGZRBH0MS150883
Stock: P9917
Certified Pre-Owned: No
Listed since: 04-24-2025 - Not Priced
- 67,542 miles
- No accidents, 2 owners, personal use
- 6cyl automatic
- Orland Toyota (22 mi away)
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Located in Tinley Park, IL / 22 miles away from Chicago, IL
2021 Toyota Highlander XSE
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: 5TDJZRBH9MS061724
Stock: P9903
Certified Pre-Owned: No
Listed since: 04-21-2025 - 53,572 miles
- 2 accidents, 1 owner, personal use only
- 6cyl automatic
- CarMax Naperville (30 mi away)
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Located in Naperville, IL / 30 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: 5TDFZRBH6MS094010
Stock: 27212361
Certified Pre-Owned: No- $33,500great price$2,450 below market
- 85,829 miles
- No accidents, 1 owner, personal use
- 6cyl automatic
- 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: 5TDDZRBH3NS170405
Stock: GA28396
Certified Pre-Owned: No
Listed since: 03-26-2025 - $37,850good price$886 below market
- 45,850 miles
- No accidents, 2 owners, personal use
- 6cyl automatic
- Zeigler Chevrolet Schaumburg (24 mi away)
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Located in Schaumburg, IL / 24 miles away from Chicago, IL
2022 Toyota Highlander XSE AWD. Celestial Silver MetallicAWD, 3.003 Axle Ratio, 3rd row seats: split-bench, 4-Wheel Disc Brakes, 6 Speakers, ABS bra...
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: 5TDLZRBHXNS235438
Stock: P1075
Certified Pre-Owned: No
Listed since: 03-18-2025 - $42,590fair price$666 below market
- 13,887 miles
- 1 accident, 1 owner, personal use
- 6cyl automatic
- 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: 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: 5TDDZRBHXNS255855
Stock: 2003495946
Certified Pre-Owned: No
Listed since: 03-18-2025 - $31,886good price$1,509 below market
- 82,579 miles
- No accidents, 1 owner, personal use only
- 6cyl automatic
- Arlington Toyota Palatine (27 mi away)
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Located in Palatine, IL / 27 miles away from Chicago, IL
AWD ONE-OWNER LOCAL TRADE & *4.9% APR FOR 72 MONTHS & 2 YEARS MAINTENANCE INCLUDED ON CERTIFIED USED VEHICLES!! *Delivers 27 Highway MPG and 20 City M...
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: 5TDGZRBH7NS198219
Stock: 19395P
Certified Pre-Owned: Yes
Listed since: 03-20-2025
Showing 1 - 21 out of 1,166 listings
Consumer Reviews for the Toyota Highlander
Read recent reviews for the Toyota Highlander
Couldn’t be happier!
S Curry, 01/02/2021
2021 Toyota Highlander Limited 4dr SUV AWD (3.5L 6cyl 8A)
I’ve been eyeing the Highlander since they redesigned it in 2020. I opted for the Limited AWD trim with the optional 12 inch screen and bench seats. I am completely blown away on how amazing it is to drive the Highlander. Visibility is great but with the bigger screen you also get birds eye view which will definitely help assess your surroundings. The safety features are awesome and the … little things like intuitive climate control are nice. I was worried about access into the third row and comfort but my 12 year old is happy with it. The middle row does slide up giving more leg room to the third row. I came from a minivan so I am used to a lot of cargo room and low entry. If you will be using the third row consistently I recommend getting the cross bars and on roof cargo storage to maximize what you can carry, and if you are transporting smaller kids/adults the step up may be just slightly too high for them but running boards can be installed.
Used 2021 Toyota Highlander in Chicago, IL Values
Estimated values
2021 Toyota Highlander XLE 4dr SUV AWD (3.5L 6cyl 8A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $29,243 | $31,093 | $32,947 |
| Clean | $28,621 | $30,415 | $32,212 |
| Average | $27,583 | $29,286 | $30,988 |
| Rough | $26,234 | $27,818 | $29,397 |
The average list price of a used 2021 Toyota Highlander in Chicago, Illinois is $37,028. The average mileage on a used Toyota Highlander 2021 for sale in Chicago, Illinois is 51,746. Based on the average mileage of 51,746 for used 2021 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 2021 in Chicago, Illinois to be $27,583.
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* Delivery of any kind does not apply to Alaska and Hawaii. Contact the dealer for delivery details, restrictions and costs.