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74 listings
- $49,777fair price$744 above market
- 1,598 miles
- No accidents, personal use only
- 7 Seats, 21 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
2025 Toyota Grand Highlander XLE AWD Only ~1,600 miles, nearly new condition. This one owner, accident free SUV seamlessly blends Toyotas latest techn...
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 (21 City/27 Highway)
Listing Information:
VIN: 5TDAAAB5XSS088832
Stock: C19753AA
Certified Pre-Owned: No
Listed since: 07-02-2025 - $50,495good price$2,206 below market
- 43,035 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 26 Hwy MPG
- Romeoville Toyota (34 mi away)
- Home delivery*
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Located in Romeoville, IL / 34 miles away from Chicago, IL
2024 Toyota Grand Highlander Platinum ***ONE OWNER***Toyota Gold Certified Details:* Vehicle History* Powertrain Limited Warranty: 84 Month/100,000 Mi...
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: 5TDAAAB52RS039036
Stock: T18673A
Certified Pre-Owned: Yes
Listed since: 06-28-2025 - $47,995fair price$245 above market
- 11,981 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 21 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,Heated Seats,Keyless S...
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 (21 City/27 Highway)
Listing Information:
VIN: 5TDAAAB5XRS061480
Stock: G92731
Certified Pre-Owned: No - New Listing$45,998fair price$16 below market
- 14,529 miles
- 8 Seats, 21 City / 27 Hwy MPG
- CarMax Waukesha (84 mi away)
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Located in Waukesha, WI / 84 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 (21 City/27 Highway)
Listing Information:
VIN: 5TDAAAB59RS048185
Stock: 27539679
Certified Pre-Owned: No - New Listing
- 20,156 miles
- No accidents, 1 owner, personal use
- 7 Seats, 21 City / 28 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:
24 Combined MPG (21 City/28 Highway)
Listing Information:
VIN: 5TDAAAA5XRS004276
Stock: 2003801748
Certified Pre-Owned: No
Listed since: 06-27-2025 - New Listing
- 42,457 miles
- No accidents, 1 owner, personal use
- 7 Seats, 21 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 (21 City/27 Highway)
Listing Information:
VIN: 5TDAAAB57RS006310
Stock: 2003912291
Certified Pre-Owned: No
Listed since: 07-28-2025 - New Listing
- 23,804 miles
- 1 accident, 1 owner, personal use only
- 8 Seats, 21 City / 27 Hwy MPG
- 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 (21 City/27 Highway)
Listing Information:
VIN: 5TDAAAB53RS003386
Stock: 27722234
Certified Pre-Owned: No - 64 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 26 Hwy MPG
- CarMax (In-stock online)
- Transfer available from VA to IL*
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Located in Fredericksburg, VA / 591 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: No
Lemon Status: No
Free History Report: Yes
Features and Specs:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDAAAB53SS084895
Stock: 27575195
Certified Pre-Owned: No- New Listing
- 1,775 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- CarMax (In-stock online)
- Transfer available from CA to IL*
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Located in San Diego, CA / 1,728 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: No
Lemon Status: No
Free History Report: No
Features and Specs:
24 Combined MPG (21 City/28 Highway)
Listing Information:
VIN: 5TDAAAA52SS021675
Stock: 26887372
Certified Pre-Owned: No - New Listing
- 3,519 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 26 Hwy MPG
- CarMax (In-stock online)
- Transfer available from WA to IL*
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Located in Puyallup, WA / 1,731 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: No
Lemon Status: No
Free History Report: No
Features and Specs:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDAAAB52SS080353
Stock: 27470534
Certified Pre-Owned: No - New Listing
- 4,280 miles
- 7 Seats, 20 City / 26 Hwy MPG
- Chevrolet of Palatine (28 mi away)
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Located in Palatine, IL / 28 miles away from Chicago, IL
2025 Toyota Grand Highlander 2.4L 4-CylinderCARFAX One-Owner. Clean CARFAX.
AutoCheck Vehicle History Summary Unavailable.
Features and Specs:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDAAAB50SS075054
Stock: TLW3618A
Certified Pre-Owned: No
Listed since: 04-12-2025 - Price Drop$45,590great price$7,775 below market
- 18,783 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 20 City / 26 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
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Located in Cleveland, OH / 307 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: 5TDAAAB57RS063784
Stock: 2003627729
Certified Pre-Owned: No
Listed since: 04-09-2025 - New Listing
- 2,133 miles
- 7 Seats, 20 City / 26 Hwy MPG
- CarMax (In-stock online)
- Transfer available from VA to IL*
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Located in Woodbridge, VA / 589 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:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDAAAB50SS088967
Stock: 26663913
Certified Pre-Owned: No - New Listing$43,489great price$4,194 below market
- 17,611 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 27 Hwy MPG
- Graff Ford of Chesterton (33 mi away)
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Located in Chesterton, IN / 33 miles away from Chicago, IL
CARFAX One-Owner.4-Wheel Disc Brakes, ABS brakes, Active Cruise Control, Air Conditioning, Alloy wheels, Auto High-beam Headlights, Auto-dimming Rear-...
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 (21 City/27 Highway)
Listing Information:
VIN: 5TDAAAB53RS058002
Stock: 34-25011A
Certified Pre-Owned: No
Listed since: 07-04-2025 - $46,990great price
- 18,985 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 20 City / 26 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
Close
Located in Dallas, TX / 803 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: 5TDAAAB54RS060468
Stock: 2003754664
Certified Pre-Owned: No
Listed since: 05-21-2025 - $43,495great price
- 26,496 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
Close
Located in Grapevine, TX / 805 miles away from Chicago, IL
CarFax No Accidents Reported,CarFax 1-Owner,Rare Find,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Hands-Free L...
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: 5TDAAAA55RS002886
Stock: RS002886A
Certified Pre-Owned: No - New Listing$45,590great price$3,450 below market
- 13,886 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 21 City / 28 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
Close
Located in Sacramento, CA / 1,788 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:
24 Combined MPG (21 City/28 Highway)
Listing Information:
VIN: 5TDAAAA55RS017372
Stock: 2003912080
Certified Pre-Owned: No
Listed since: 07-29-2025 - $43,124great price$3,348 below market
- 25,260 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 27 Hwy MPG
- Van Horn Honda of Glendale (87 mi away)
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Located in Glendale, WI / 87 miles away from Chicago, IL
3rd Row Seats, Heated Front Seats, Heated Steering Wheel, Adaptive Cruise, Blind Spot Monitor w/ Rear Cross Traffic Alert, Lane Keep Assist, Lane Depa...
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 (21 City/27 Highway)
Listing Information:
VIN: 5TDAAAB54RS001713
Stock: V204686
Certified Pre-Owned: No
Listed since: 05-15-2025 - New Listing$42,990great price$3,127 below market
- 19,327 miles
- No accidents, 1 owner, corporate fleet vehicle
- 7 Seats, 21 City / 27 Hwy MPG
- Elgin Toyota (31 mi away)
- Home delivery*
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Located in Streamwood, IL / 31 miles away from Chicago, IL
2024 Toyota Grand Highlander XLE AWD Modern Space, Premium Comfort, and Family Versatility in Midnight Black MetallicGet the extra room you need and t...
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 (21 City/27 Highway)
Listing Information:
VIN: 5TDAAAB51RS060752
Stock: P20749
Certified Pre-Owned: No
Listed since: 05-25-2025 - $47,490great price$2,996 below market
- 52,377 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 26 Hwy MPG
- Elgin Toyota (31 mi away)
- Home delivery*
Close
Located in Streamwood, IL / 31 miles away from Chicago, IL
2024 Toyota Grand Highlander Platinum AWD Spacious, Sophisticated, and Adventure-Ready in Celestial Silver MetallicStep into the ultimate family SUV w...
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: 5TDAAAB52RS003881
Stock: P20724
Certified Pre-Owned: No
Listed since: 07-17-2025 - Price Drop$50,590good price$1,470 below market
- 20,096 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 26 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
Close
Located in Memphis, TN / 484 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: 5TDAAAB51RS044308
Stock: 2003671181
Certified Pre-Owned: No
Listed since: 06-25-2025
Showing 1 - 21 out of 74 listings
Consumer Reviews for the Toyota Grand Highlander
Read recent reviews for the Toyota Grand Highlander
Never again
(ex)Loyal Toyota lover , 06/27/2024
2024 Toyota Grand Highlander Limited 4dr SUV AWD (2.4L 4cyl Turbo 8A)
We (collectively as a family including my parents) have owned over 30 Toyotas in our life. We have loved everyone of them except this one. We made the HUGE mistake of being the first in NM to grab one right as it came off the finish line last June. Within a month we started having issues with the head unit. We took it in 3 times. They " reset or updated", it and then told us that … there had to be 3000 complaints about the same issue before they could do any more OR it had to duplicate the issue for them. ( We had videos each time on the first three visits). 23 videos later ( one which lasted 17 minutes) we took it back in and told them to keep it and drive it as long as they had to , to reduplicate the issue as it was happening several times a week. ( Navigation would not work, and the rearview camara would pop on while driving down the road- super distractive when you have this massive screen next to your driving wheel. wheel). Anyhow miraculously the car acted up for them and ta dah.... the head unit. The same thing we had told them from the first visit. Fast forward 6 weeks. The part was on back order. ( keep in mind there was supposedly no one else having these issues.). Car goes back to the shop two weeks ago, only to have the WRONG head unit. Promised they found one in Phoenix and issue would be fixed the following morning. Here we sit......... ( did I mention we have been waiting on a part that is only a six hour drive from us for 6 days???). I am to take back my rental tomorrow, because now they have no idea when the part will be in. I have never been SO disgusted with a dealership over a car as I am right now. I seriously want out of this car BAD but I only have about 8,000 in equity which is not sufficient to find another large SUV I can afford.
Used 2025 Toyota Grand Highlander in Chicago, IL Values
Estimated values
2025 Toyota Grand Highlander XLE 4dr SUV AWD (2.4L 4cyl Turbo 8A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $35,871 | $36,878 | $38,087 |
| Clean | $35,682 | $36,633 | $37,781 |
| Average | $35,367 | $36,224 | $37,272 |
| Rough | $34,957 | $35,693 | $36,610 |
The average list price of a used 2025 Toyota Grand Highlander in Chicago, Illinois is $48,919. The average mileage on a used Toyota Grand Highlander 2025 for sale in Chicago, Illinois is 18,198. Based on the average mileage of 18,198 for used 2025 Toyota Grand 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 Grand Highlander 2025 in Chicago, Illinois to be $35,367.
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