Used Toyota Grand Highlander for Sale in Chicago, IL
Shop for a luxurious Toyota Grand Highlander in the Windy City
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33 listings
- 7,859 miles
- No accidents, 1 owner, personal use only
- 4cyl automatic
- Orland Toyota (22 mi away)
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Located in Tinley Park, IL / 22 miles away from Chicago, IL
2024 Toyota Grand Highlander XLE **LIKE BRAND NEW, **BLACK BEAUTY, **LOW MILES ONLY 7859, **1 OWNER CLEAN CARFAX, **NAVIGATION, **BLUETOOTH, **LEATHER...
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: 5TDAAAB5XRS001618
Stock: P9857
Certified Pre-Owned: Yes
Listed since: 03-18-2025- Price Drop$47,590great price$8,008 below market
- 18,783 miles
- No accidents, 1 owner, rental vehicle
- 4cyl automatic
- 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: 04-08-2025 - $48,000good price$2,153 below market
- 12,760 miles
- No accidents, 1 owner, personal use only
- 4cyl automatic
- Driveway (In-stock online)
- Home delivery*
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Located in North Brunswick, NJ / 691 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:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDAAAB56RS028332
Stock: SS038012A
Certified Pre-Owned: No - Price Drop$45,998great price$3,153 below market
- 12,094 miles
- No accidents, 1 owner, rental vehicle
- 4cyl automatic
- Driveway (In-stock online)
- Home delivery*
Close
Located in Wexford, PA / 403 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: 5TDAAAB59RS056223
Stock: A056223P
Certified Pre-Owned: No - $48,998fair price$705 below market
- 10,854 miles
- No accidents, 1 owner, personal use
- 4cyl automatic
- CarMax (In-stock online)
- Transfer available from OR to IL*
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Located in Salem, OR / 1,773 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:
23 Combined MPG (21 City/27 Highway)
Listing Information:
VIN: 5TDAAAB55RS048748
Stock: 26833804
Certified Pre-Owned: No - Price Drop$50,460good price$3,038 below market
- 25,144 miles
- No accidents, 1 owner, personal use
- 4cyl automatic
- Driveway (In-stock online)
- Home delivery*
Close
Located in Ramsey, NJ / 700 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,Chrome Wheels,Cooled S...
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: 5TDAAAB59RS015820
Stock: L17059P
Certified Pre-Owned: No - $52,998fair price
- 18,368 miles
- No accidents, 1 owner, personal use only
- 4cyl automatic
- CarMax (In-stock online)
- Transfer available from TX to IL*
Close
Located in Fort Worth, TX / 831 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: 5TDAAAB52RS055348
Stock: 27139075
Certified Pre-Owned: No - $48,398fair price$251 below market
- 18,753 miles
- No accidents, 1 owner, rental vehicle
- 4cyl automatic
- Enterprise Car Sales (In-stock online)
- Home delivery*
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Located in Highlands Ranch, CO / 917 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: 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: 5TDAAAB51RS040663
Stock: 8F0RC3
Certified Pre-Owned: No
Listed since: 03-10-2025 - New Listing$46,998fair price$416 below market
- 22,461 miles
- No accidents, 1 owner, personal use only
- 4cyl automatic
- CarMax (In-stock online)
- Transfer available from VA to IL*
Close
Located in Richmond, VA / 608 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:
23 Combined MPG (21 City/27 Highway)
Listing Information:
VIN: 5TDAAAB5XRS051743
Stock: 26588290
Certified Pre-Owned: No - New Listing$48,998fair price$101 above market
- 5,574 miles
- No accidents, 1 owner, personal use only
- 4cyl automatic
- CarMax (In-stock online)
- Transfer available from MD to IL*
Close
Located in Gaithersburg, MD / 581 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:
23 Combined MPG (21 City/27 Highway)
Listing Information:
VIN: 5TDAAAB58RS020913
Stock: 26966174
Certified Pre-Owned: No - $48,998fair price$630 above market
- 1,559 miles
- No accidents, 1 owner, personal use only
- 4cyl automatic
- CarMax (In-stock online)
- Transfer available from VA to IL*
Close
Located in Lynchburg, VA / 547 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:
23 Combined MPG (21 City/27 Highway)
Listing Information:
VIN: 5TDAAAB59RS064015
Stock: 26672908
Certified Pre-Owned: No - 11,983 miles
- No accidents, 1 owner, personal use only
- 4cyl automatic
- Driveway (In-stock online)
- Home delivery*
Close
Located in Portland, OR / 1,755 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,Chrome Wheels,Cooled S...
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: 5TDAAAB58RS021589
Stock: RS021589T
Certified Pre-Owned: No- $47,998fair price$787 above market
- 12,559 miles
- No accidents, 2 owners, personal use
- 4cyl automatic
- CarMax (In-stock online)
- Transfer available from CO to IL*
Close
Located in Loveland, CO / 907 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:
23 Combined MPG (21 City/27 Highway)
Listing Information:
VIN: 5TDAAAB51RS026102
Stock: 26755834
Certified Pre-Owned: No - Price Drop$51,990fair price$712 above market
- 14,125 miles
- No accidents, 2 owners, personal use only
- 4cyl automatic
- Driveway (In-stock online)
- Home delivery*
Close
Located in Chesapeake, VA / 705 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:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDAAAB55RS000652
Stock: RS000652P
Certified Pre-Owned: No - $43,799good price$2,099 below market
- 33,565 miles
- No accidents, 1 owner, personal use only
- 4cyl automatic
- Driveway (In-stock online)
- Home delivery*
Close
Located in Wesley Chapel, FL / 986 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: 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: 5TDAAAA5XRS015052
Stock: RS015052A
Certified Pre-Owned: No - Price Drop$56,590fair price$1,740 below market
- 16,412 miles
- No accidents, 2 owners, personal use only
- 4cyl automatic
- Carvana (In-stock online)
- Home delivery*
Close
Located in Oklahoma City, OK / 692 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: 5TDAAAB55RS037247
Stock: 2003642745
Certified Pre-Owned: No
Listed since: 04-11-2025 - New Listing$52,990good price$1,315 below market
- 13,259 miles
- No accidents, 1 owner, personal use
- 4cyl automatic
- Carvana (In-stock online)
- Home delivery*
Close
Located in Tampa, FL / 1,005 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: 5TDAAAB54RS048255
Stock: 2003638718
Certified Pre-Owned: No
Listed since: 04-04-2025 - New Listing$45,089good price$1,832 below market
- 23,172 miles
- No accidents, 1 owner, rental vehicle
- 4cyl automatic
- Castle Volkswagen Downers Grove (21 mi away)
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Located in Downers Grove, IL / 21 miles away from Chicago, IL
2024 Toyota Grand Highlander XLE Storm Cloud *7 PASSENGER, All our pre-owned vehicles come with our Castle Downers Grove peace of mind powertrain warr...
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: 5TDAAAB55RS057708
Stock: PDV0470
Certified Pre-Owned: No
Listed since: 02-07-2025 - $48,315fair price$369 below market
- 17,486 miles
- No accidents, 1 owner, personal use only
- 4cyl automatic
- Oak Lawn Toyota (12 mi away)
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Located in Oak Lawn, IL / 12 miles away from Chicago, IL
*Heated Front Seats* *Heated Steering WheelOur 2024 Toyota Grand Highlander XLE AWD gives your family more room to make more memories in Midnight Blac...
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: 5TDAAAB50RS057714
Stock: P0465
Certified Pre-Owned: Yes
Listed since: 03-20-2025 - New Listing$46,998fair price$87 below market
- 18,357 miles
- 4cyl automatic
- CarMax (In-stock online)
- Transfer available from VA to IL*
Close
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 Unavailable.
Features and Specs:
23 Combined MPG (21 City/27 Highway)
Listing Information:
VIN: 5TDAAAB58RS009006
Stock: 26470589
Certified Pre-Owned: No - $56,998fair price$258 above market
- 3,236 miles
- No accidents, 1 owner, personal use only
- 4cyl automatic
- Genesis of Schaumburg (25 mi away)
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Located in Schaumburg, IL / 25 miles away from Chicago, IL
Our used car manager appraised & prepared this vehicle as though he was selling to a family member. Comes with a FREE Carfax history report, optional ...
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: 5TDAAAB54RS063158
Stock: G8527A
Certified Pre-Owned: No
Listed since: 04-08-2025
Showing 1 - 21 out of 33 listings
Consumer Reviews for the Toyota Grand Highlander
Read recent reviews for the Toyota Grand Highlander
No Regrets!
Allison K. , 01/24/2024
2024 Toyota Grand Highlander
Absolutely love my Grand Highlander. Just hit over 5000 miles and haven’t had any issues. It’s comfortable and has plenty of storage space, even with the 3rd row up. Only issue I have is getting the system to connect to the right phone based on who is in the car. Can’t get it to switch between the driver’s profiles. Sometimes you can have too much technology.
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