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1,628 listings
- $32,990fair price$44 below market
- 55,311 miles
- 1 accident, 1 owner, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- Lexus of Merrillville (30 mi away)
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Located in Merrillville, IN / 30 miles away from Chicago, IL
BLIND SPOT MONITOR!, ONE OWNER!, LOW MILEAGE!, MOONROOF!, Magnetic Gray Metallic 2021 Toyota Highlander XLE AWD 8-Speed Automatic 3.5L V6 DOHC 18" Mac...
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: 5TDGZRBH1MS060299
Stock: LM03781
Certified Pre-Owned: No
Listed since: 04-26-2025 - Price Drop$33,942good price$1,175 below market
- 72,809 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Zeigler Buick GMC of Lincolnwood (11 mi away)
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Located in Lincolnwood, IL / 11 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 - $37,999fair price$242 above market
- 8,728 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 22 City / 29 Hwy MPG
- Orland Toyota (21 mi away)
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Located in Tinley Park, IL / 21 miles away from Chicago, IL
2023 Toyota Highlander L **LIKE BRAND NEW, **LOCAL TRADE, **TOYOTA CERTIFIED, **LOW MILES ONLY 8728, **1 OWNER CLEAN CARFAX, **BLUETOOTH, **CLOTH SEAT...
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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH8PS509721
Stock: 457241
Certified Pre-Owned: Yes
Listed since: 06-09-2025 - 15,422 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- Golf Mill Ford (17 mi away)
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Located in Niles, IL / 17 miles away from Chicago, IL
2023 Toyota Highlander XSE Midnight Black Metallic AWD 4D Sport Utility2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hp 8-Speed AutomaticClean CAR...
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/28 Highway)
Listing Information:
VIN: 5TDKDRBH3PS519930
Stock: X15026
Certified Pre-Owned: No
Listed since: 04-22-2025- $34,990good price$1,357 below market
- 25,875 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Fields Chrysler Jeep Dodge Ram (19 mi away)
- Home delivery*
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Located in Glenview, IL / 19 miles away from Chicago, IL
Fields Chrysler Jeep Dodge Ram and SRT of Glenview carries a wide array of used cars, as well as certified pre-owned Chrysler, Jeep and Dodge vehicles...
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: 5TDGZRBH8MS557642
Stock: J38963A
Certified Pre-Owned: No
Listed since: 06-24-2025 - $38,990good price$1,443 below market
- 41,969 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 21 City / 28 Hwy MPG
- Zeigler Toyota of Racine (62 mi away)
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Located in Mount Pleasant, WI / 62 miles away from Chicago, IL
One Owner - Clean History Report Showing No Accidents ++, 3rd row seats: split-bench, ABS brakes, Active Cruise Control, Alloy wheels, Electronic Stab...
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:
24 Combined MPG (21 City/28 Highway)
Listing Information:
VIN: 5TDKDRBH2PS511477
Stock: PS511477
Certified Pre-Owned: Yes
Listed since: 04-08-2025 - $36,999fair price$146 above market
- 8,848 miles
- No accidents, 1 owner, personal use
- 8 Seats, 22 City / 29 Hwy MPG
- Pauly Toyota (42 mi away)
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Located in Crystal Lake, IL / 42 miles away from Chicago, IL
CARFAX One-Owner. Clean CARFAX. Certified. Celestial Silver Metallic 2023 Toyota Highlander L TOYOTA GOLD CERTIFIED FWD 8-Speed Automatic 2.4L I4 PDI ...
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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH9PS500123
Stock: 40083B
Certified Pre-Owned: Yes
Listed since: 06-10-2025 - $40,588fair price$962 below market
- 35,846 miles
- No accidents, 1 owner, corporate fleet vehicle
- 7 Seats, 22 City / 29 Hwy MPG
- Umansky Chevrolet (88 mi away)
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Located in Glendale, WI / 88 miles away from Chicago, IL
Discover the perfect blend of luxury, performance, and reliability with this 2023 Toyota Highlander Limited in stunning Magnetic Gray Metallic, now av...
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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH8PS015603
Stock: P15603
Certified Pre-Owned: No
Listed since: 06-18-2025 - $35,500fair price$351 below market
- 73,884 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- CarWise Gurnee (40 mi away)
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Located in Gurnee, IL / 40 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 - Price Drop$38,516fair price$973 below market
- 43,007 miles
- No accidents, 1 owner, personal use
- 8 Seats, 21 City / 28 Hwy MPG
- Zeigler Toyota of Racine (62 mi away)
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Located in Mount Pleasant, WI / 62 miles away from Chicago, IL
One Owner - Clean History Report Showing No Accidents ++, 3rd row seats: split-bench, ABS brakes, Active Cruise Control, Alloy wheels, Electronic Stab...
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/28 Highway)
Listing Information:
VIN: 5TDKDRBH2PS520003
Stock: PS520003
Certified Pre-Owned: No
Listed since: 06-18-2025 - $35,844good price$1,064 below market
- 74,249 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 21 City / 28 Hwy MPG
- Umansky Toyota (88 mi away)
Close
Located in Milwaukee, WI / 88 miles away from Chicago, IL
Elevate your driving experience with the 2023 Toyota Highlander XLE, available now at Umansky Toyota in Milwaukee, Wisconsin. Dressed in a sleek Midni...
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/28 Highway)
Listing Information:
VIN: 5TDKDRBH4PS044787
Stock: T74745A
Certified Pre-Owned: Yes
Listed since: 06-10-2025 - $39,585fair price$786 below market
- 43,747 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 21 City / 28 Hwy MPG
- Toyota of Brookfield (89 mi away)
Close
Located in Brookfield, WI / 89 miles away from Chicago, IL
CARFAX One-Owner. Clean CARFAX. Certified. Wind Chill Pearl 2023 Toyota Highlander XLE AWD 8-Speed Automatic 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SU...
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:
24 Combined MPG (21 City/28 Highway)
Listing Information:
VIN: 5TDKDRBH7PS507943
Stock: PSW1013
Certified Pre-Owned: Yes
Listed since: 06-04-2025 - 82,029 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- CarMax Tinley Park (23 mi away)
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Located in Tinley Park, IL / 23 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: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: Yes
Lemon Status: No
Free History Report: No
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDJZRBHXMS100434
Stock: 27246475
Certified Pre-Owned: No- Price Drop
- 11,956 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 28 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, ** Blue...
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/28 Highway)
Listing Information:
VIN: 5TDKDRBHXPS009669
Stock: Q9401
Certified Pre-Owned: Yes
Listed since: 04-19-2025 - 32,221 miles
- No accidents, 1 owner, personal use
- 8 Seats, 20 City / 27 Hwy MPG
- Orland Toyota (21 mi away)
Close
Located in Tinley Park, IL / 21 miles away from Chicago, IL
2021 Toyota Highlander XLE **LIKE NEW, **TOYOTA CERTIFIED, **MILES ONLY 32221, **1 OWNER CLEAN CARFAX, **NAVIGATION, **BLUETOOTH, **LEATHER SEATS, **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: 5TDHZRBH8MS111608
Stock: P9911
Certified Pre-Owned: Yes
Listed since: 04-21-2025- $39,497fair price$85 below market
- 45,463 miles
- No accidents, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- CarWise Gurnee (40 mi away)
Close
Located in Gurnee, IL / 40 miles away from Chicago, IL
AWD.Clean CARFAX. Odometer is 8235 miles below market average! Silver 2021 Toyota Highlander 4D Sport Utility Platinum 3.5L V6 DOHC 20/27 City/High...
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 - $33,479good price$1,488 below market
- 48,726 miles
- 1 accident, 1 owner, personal use
- 8 Seats, 20 City / 27 Hwy MPG
- Zeigler Toyota of Racine (62 mi away)
Close
Located in Mount Pleasant, WI / 62 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: Yes
Listed since: 05-06-2025 - 63,376 miles
- No accidents, 1 owner, corporate fleet vehicle
- 8 Seats, 20 City / 27 Hwy MPG
- Orland Toyota (21 mi away)
Close
Located in Tinley Park, IL / 21 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 (21 mi away)
Close
Located in Tinley Park, IL / 21 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- New Listing$37,366fair price$995 above market
- 65,580 miles
- No accidents, 1 owner, personal use
- 8 Seats, 21 City / 28 Hwy MPG
- Enterprise Car Sales Aurora (31 mi away)
- Home delivery*
Close
Located in Aurora, IL / 31 miles away from Chicago, IL
Transfer of vehicle from another location to your neighborhood Enterprise Car Sales may require payment of a non-refundable transfer fee to begin the ...
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/28 Highway)
Listing Information:
VIN: 5TDKDRBH4PS007450
Stock: 8GJ1HD
Certified Pre-Owned: No
Listed since: 06-23-2025 - 12,287 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- Orland Toyota (21 mi away)
Close
Located in Tinley Park, IL / 21 miles away from Chicago, IL
2023 Toyota Highlander Limited **LIKE BRAND NEW, **LOCAL TRADE, **TOYOTA CERTIFIED, **MILES ONLY 12287, **1 OWNER CLEAN CARFAX, **NAVIGATION, **BLUETO...
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/28 Highway)
Listing Information:
VIN: 5TDKDRBH1PS004621
Stock: 454891
Certified Pre-Owned: No
Listed since: 04-14-2025
Showing 43 - 63 out of 1,628 listings
Consumer Reviews for the Toyota Highlander
Read recent reviews for the Toyota Highlander
Rolling again
Ken S, 10/28/2021
2022 Toyota Highlander Limited 4dr SUV AWD (3.5L 6cyl 8A)
Just replaced a 2018 Highlander due to accident. Of course the car is comfortable and nice to drive but I especially appreciate it after the accident. The 2018 was totaled because of a head on collision. My wife and I only had minor injuries that I attribute to the strength of the vehicle and the air bags that completely isolated us.
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 | $31,135 | $33,215 | $35,302 |
| Clean | $30,472 | $32,491 | $34,515 |
| Average | $29,367 | $31,285 | $33,204 |
| Rough | $27,931 | $29,717 | $31,498 |
The average list price of a used 2021 Toyota Highlander in Chicago, Illinois is $38,344. The average mileage on a used Toyota Highlander 2021 for sale in Chicago, Illinois is 44,134. Based on the average mileage of 44,134 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 $29,367.
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* Delivery of any kind does not apply to Alaska and Hawaii. Contact the dealer for delivery details, restrictions and costs.