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1,474 listings
- $37,980good price$910 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 - $34,497good price$2,094 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 - Price Drop$32,779good price$1,685 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 - $35,990fair price$195 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*
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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: 5TDGZRBH5MS160129
Stock: 2003862153
Certified Pre-Owned: No
Listed since: 07-12-2025 - $35,311good price$1,508 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 - $35,990fair price$183 below market
- 35,444 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: 5TDHZRBH8MS056982
Stock: 2003858064
Certified Pre-Owned: No
Listed since: 07-09-2025 - $35,100fair price$178 below market
- 73,884 miles
- No accidents, 1 owner, 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: 5TDFZRBH1MS067670
Stock: GL28864
Certified Pre-Owned: No
Listed since: 05-21-2025 - $33,955good price$874 below market
- 91,248 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Driveway (80 mi away)
- Home delivery*
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Located in West Allis, WI / 80 miles away from Chicago, IL
CarFax No Accidents Reported,CarFax 1-Owner,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Hands-Free Liftgate,He...
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: 5TDFZRBHXMS124688
Stock: N21399
Certified Pre-Owned: No - $25,950good price$931 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 - $27,490fair price$363 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 - Price Drop$32,790fair price$38 above market
- 54,512 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- Lexus of Merrillville (31 mi away)
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Located in Merrillville, IN / 31 miles away from Chicago, IL
BLIND SPOT MONITOR!, LEXUS SAFETY SYSTEM PLUS!, ONE OWNER!, LOW MILEAGE!, MOONROOF!, Magnetic Gray Metallic 2021 Toyota Highlander XLE AWD 8-Speed Aut...
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: 5TDGZRBH8MS538895
Stock: LM05511
Certified Pre-Owned: No
Listed since: 07-11-2025 - $35,590fair price$187 above market
- 34,557 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: 5TDGZRBH9MS057182
Stock: 2003886645
Certified Pre-Owned: No
Listed since: 07-09-2025 - $32,997fair price$579 below market
- 48,726 miles
- 1 accident, 1 owner, personal use
- 8 Seats, 20 City / 27 Hwy MPG
- Zeigler Toyota of Racine (60 mi away)
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Located in Mount Pleasant, WI / 60 miles away from Chicago, IL
One Owner ++, 18" Machined Alloy Wheels, 3rd row seats: split-bench, Front Bucket Seats, Heated front seats, Power driver seat, Power Liftgate, Power ...
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: 5TDGZRBH8MS554093
Stock: MS554093
Certified Pre-Owned: No
Listed since: 05-06-2025 - $35,926fair price$469 above market
- 72,587 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Victory Nissan Chesterton (33 mi away)
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Located in Chesterton, IN / 33 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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDFZRBH8MS123118
Stock: 91E07801
Certified Pre-Owned: No
Listed since: 07-18-2025 - 50,051 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Orland Toyota (22 mi away)
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Located in Tinley Park, IL / 22 miles away from Chicago, IL
2021 Toyota Highlander XSE **LIKE NEW, **TOYOTA CERTIFIED, **LOW MILES ONLY 50051, **1 OWNER CLEAN CARFAX, **NAVIGATION, **BLUETOOTH, **LEATHER SEATS,...
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: 5TDLZRBH2MS061024
Stock: P9944
Certified Pre-Owned: Yes
Listed since: 05-14-2025- 30,893 miles
- No accidents, 1 owner, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Pauly Toyota (41 mi away)
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Located in Crystal Lake, IL / 41 miles away from Chicago, IL
CARFAX One-Owner. Clean CARFAX. Certified. Moon Dust 2021 Toyota Highlander XLE TOYOTA GOLD CERTIFIED AWD 8-Speed Automatic 3.5L V6 DOHC Toyota Gold C...
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: 5TDGZRBH6MS155473
Stock: XX7473
Certified Pre-Owned: Yes
Listed since: 05-19-2025- 63,376 miles
- No accidents, 1 owner, corporate fleet vehicle
- 8 Seats, 20 City / 27 Hwy MPG
- Orland Toyota (22 mi away)
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Located in Tinley Park, IL / 22 miles away from Chicago, IL
2021 Toyota Highlander XLE **LIKE NEW, **TOYOTA CERTIFIED, **MILES ONLY 63376, **1 OWNER CLEAN CARFAX, **BLUETOOTH, **LEATHER SEATS, **HEATED SEATS, *...
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: Yes
Listed since: 04-24-2025- 65,472 miles
- No accidents, 2 owners, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Orland Toyota (22 mi away)
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Located in Tinley Park, IL / 22 miles away from Chicago, IL
2021 Toyota Highlander XLE **LIKE BRAND NEW, **TOYOTA CERTIFIED, **1 OWNER CLEAN CARFAX, **BLUETOOTH, **LEATHER SEATS, **HEATED SEATS, **POWER MOONROO...
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: Yes
Listed since: 04-24-2025- Not provided
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- 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- Price Drop
- 49,572 miles
- 1 accident, 1 owner, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- Taylor Chrysler Dodge Jeep Ram (51 mi away)
- Home delivery*
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Located in Bourbonnais, IL / 51 miles away from Chicago, IL
2021 Toyota Highlander XLERed3.5L V6 DOHC 8-Speed Automatic AWDCheck out this 2021 Highlander available now at Taylor Chrysler Dodge Jeep Ram in...
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: 5TDGZRBHXMS542723
Stock: B5216A
Certified Pre-Owned: No
Listed since: 05-13-2025 - Price Drop$36,794great price$3,281 below market
- 27,713 miles
- No accidents, 1 owner, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Zeigler Honda of Racine (60 mi away)
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Located in Mount Pleasant, WI / 60 miles away from Chicago, IL
1 OWNER CLEAN CARFAX!Priced below KBB Fair Purchase Price!Odometer is 15744 miles below market average!AWD ++, APPLE CARPLAY, ANDROID AUTO, BLI...
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: 5TDLZRBH4NS178864
Stock: P12481
Certified Pre-Owned: No
Listed since: 05-02-2025
Showing 1 - 21 out of 1,474 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 Platinum 4dr SUV AWD (3.5L 6cyl 8A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $33,679 | $36,287 | $38,903 |
| Clean | $32,962 | $35,496 | $38,035 |
| Average | $31,767 | $34,178 | $36,590 |
| Rough | $30,214 | $32,465 | $34,711 |
The average list price of a used 2021 Toyota Highlander in Chicago, Illinois is $35,600. The average mileage on a used Toyota Highlander 2021 for sale in Chicago, Illinois is 54,126. Based on the average mileage of 54,126 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 $31,767.
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