Used Toyota Highlander for Sale in Chicago, IL
Buy a versatile Toyota Highlander in the Windy City
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1,153 listings
- Price Drop$31,900great price$3,659 below market
- 18,879 miles
- 1 accident, 2 owners, personal use
- 8 Seats, 22 City / 29 Hwy MPG
- International Subaru (22 mi away)
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Located in Tinley Park, IL / 22 miles away from Chicago, IL
*JUST REDUCED*, PRICE BELOW MARKET VALUE!, Highlander L, Multiple Finance Options Available, GREAT BUY!!!, 18" Painted Alloy Wheels, 3.329 Axle Ratio,...
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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH1PS514386
Stock: PS514386
Certified Pre-Owned: No
Listed since: 05-20-2025 - $42,455good price$1,617 below market
- 28,925 miles
- No accidents, 1 owner, personal use
- 8 Seats, 22 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
Our One Owner 2024 Toyota Highlander XSE takes a fierce approach to family travel in Midnight Black Metallic! Powered by a TurboCharged 2.4 Liter 4 Cy...
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: 5TDKDRAH6RS530294
Stock: 4097
Certified Pre-Owned: No
Listed since: 06-09-2025 - New Listing$26,990great price$1,943 below market
- 111,340 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Auto Gallery Chicago (19 mi away)
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Located in Addison, IL / 19 miles away from Chicago, IL
Visit Auto Gallery of Chicago to shop our great deals. You can call 630-628-1400 to schedule your test drive today.
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: 5TDGZRBH8NS571932
Stock: 7091
Certified Pre-Owned: No
Listed since: 07-26-2025 - $34,497good price$2,059 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 18265 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 - $37,999fair price$267 above market
- 8,728 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 22 City / 29 Hwy MPG
- Orland Toyota (22 mi away)
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Located in Tinley Park, IL / 22 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 - Price Drop$33,777fair price$368 above market
- 26,186 miles
- No accidents, 1 owner, corporate fleet vehicle
- 8 Seats, 20 City / 27 Hwy MPG
- Castle Hyundai Oak Lawn (12 mi away)
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Located in Oak Lawn, IL / 12 miles away from Chicago, IL
Contact us at 708-3571978 today for more information and to schedule a VIP appointment. VEHICLE LOCATION CASTLE HYUNDAI 9121 S CICERO AVE, OAKLAWN IL ...
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: 5TDBZRBH5NS586219
Stock: P4931
Certified Pre-Owned: No
Listed since: 06-13-2025 - $38,988good price$1,015 below market
- 20,365 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- McGrath Lexus of Chicago (2 mi away)
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Located in Chicago, IL / 2 miles away from Chicago, IL
Recent Arrival! Wind Chill Pearl 2022 Toyota Highlander XLE **APPLE CARPLAY & ANDROID AUTO, **HEATED SEATS, **SUNROOF/MOONROOF, **AWD, **BACK-UP CAMER...
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: 5TDHZRBH6NS586238
Stock: S1435A
Certified Pre-Owned: No
Listed since: 07-05-2025 - $31,550good price$2,133 below market
- 44,188 miles
- No accidents, 2 owners, corporate fleet vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- iDrive Motor Sports (9 mi away)
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Located in Berwyn, IL / 9 miles away from Chicago, IL
This 2023 Toyota Highlander L, has a Celestial Silver Metallic exterior and an Graphite interior color. 44188 miles. Stock Number 10109. You c...
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: 5TDKDRAH2PS005438
Stock: 10109
Certified Pre-Owned: No
Listed since: 05-13-2025 - $38,998good price$1,320 below market
- 15,860 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 21 City / 28 Hwy MPG
- CarMax Tinley Park (25 mi away)
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Located in Tinley Park, IL / 25 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: 5TDKDRBH8RS556961
Stock: 27515950
Certified Pre-Owned: No - $40,819good price$854 below market
- 26,511 miles
- No accidents, 1 owner, personal use
- 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
2022 Toyota Highlander Limited Black AWD*, NAVIGATION w/BACKUP CAMERA*, BLUETOOTH w/MUSIC STREAMING*, BLIND SPOT MONITOR*, PRE-COLLSION WARNING SYSTEM...
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: 5TDDZRBH9NS569822
Stock: PA8092
Certified Pre-Owned: No
Listed since: 06-24-2025 - $19,433good price$656 below market
- 144,611 miles
- No accidents, 2 owners, personal use
- 7 Seats, 20 City / 26 Hwy MPG
- Gerald Honda of Countryside (14 mi away)
Close
Located in Countryside, IL / 14 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:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDJZRFH1JS862525
Stock: P8796A
Certified Pre-Owned: No
Listed since: 07-02-2025 - Price Drop$32,779good price$1,703 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)
Close
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 - Price Drop$20,981good price$1,277 below market
- 138,514 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 20 City / 26 Hwy MPG
- Murgado Ford of Chicago (4 mi away)
Close
Located in Chicago, IL / 4 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:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDJZRFH0KS960110
Stock: FB07005A
Certified Pre-Owned: No
Listed since: 06-25-2025 - New Listing$9,995great price$2,525 below market
- 127,014 miles
- 2 accidents, 4 owners, personal use
- 7 Seats, 18 City / 24 Hwy MPG
- Baha Auto (13 mi away)
Close
Located in Burbank, IL / 13 miles away from Chicago, IL
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:
20 Combined MPG (18 City/24 Highway)
Listing Information:
VIN: JTEYK3EH9A2102556
Stock: B31914B
Certified Pre-Owned: No - Price Drop$36,500good price$1,265 below market
- 30,135 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 21 City / 28 Hwy MPG
- Al Piemonte Nissan (12 mi away)
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Located in Melrose Park, IL / 12 miles away from Chicago, IL
Gray 2024 Toyota Highlander LE AWD 8-Speed Automatic 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hp CARFAX CERTIFIED, RECENTLY SERVICED, COME ON...
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: 5TDKDRBH8RS533275
Stock: N14567
Certified Pre-Owned: No
Listed since: 03-13-2025 - Price Drop$38,897fair price$130 below market
- 31,211 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Packey Webb Ford (21 mi away)
- Home delivery*
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Located in Downers Grove, IL / 21 miles away from Chicago, IL
Odometer is 9632 miles below market average! 20/27 Tow Hitch Receiver w/ Wiring HarnessPremium AudioSince 1962, the Webb Family has been providi...
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: 5TDHZRBH4NS251804
Stock: 25T1284A
Certified Pre-Owned: No
Listed since: 05-19-2025 - Price Drop$44,998fair price$200 above market
- 15,422 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- Golf Mill Ford (16 mi away)
Close
Located in Niles, IL / 16 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 - Price Drop$29,808fair price$48 below market
- 87,357 miles
- No accidents, 1 owner, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Lexus of Orland (22 mi away)
Close
Located in Orland Park, IL / 22 miles away from Chicago, IL
Blizzard Pearl 2020 Toyota Highlander Limited AWD 8-Speed Automatic 3.5L V6 DOHC NAVIGATION!, LOCAL TRADE!, GREAT VEHICLE HISTORY!, PARK ASSIST, BACK ...
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: 5TDDZRBH5LS003993
Stock: LX07821
Certified Pre-Owned: No
Listed since: 07-02-2025 - Price Drop$20,899fair price$791 below market
- 66,688 miles
- 1 accident, 3 owners, personal use only
- 7 Seats, 18 City / 24 Hwy MPG
- Zeigler Cadillac of Lincolnwood (11 mi away)
Close
Located in Lincolnwood, IL / 11 miles away from Chicago, IL
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:
20 Combined MPG (18 City/24 Highway)
Listing Information:
VIN: 5TDJKRFH9FS134673
Stock: P4433A
Certified Pre-Owned: No
Listed since: 06-25-2025 - $37,900fair price$52 below market
- 17,622 miles
- 1 accident, personal use only
- 8 Seats, 21 City / 28 Hwy MPG
- Bredemann Toyota (15 mi away)
Close
Located in Park Ridge, IL / 15 miles away from Chicago, IL
FRESH OIL CHANGE - NEW CABIN AIR FILTER - NEW ENGINE FILTER - NEW WIPERS ONLY 17K MILES AND FULLY DETAILED! For 100 years, families have trusted the B...
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: Yes
Features and Specs:
24 Combined MPG (21 City/28 Highway)
Listing Information:
VIN: 5TDKDRBH5PS037749
Stock: TP7795
Certified Pre-Owned: No
Listed since: 07-17-2025 - New Listing$15,999great price$2,530 below market
- 145,648 miles
- 2 accidents, 1 owner, personal use only
- 7 Seats, 20 City / 26 Hwy MPG
- I-80 Auto Sales (21 mi away)
Close
Located in Hazel Crest, IL / 21 miles away from Chicago, IL
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:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDJZRFHXHS457824
Stock: 457824
Certified Pre-Owned: No
Showing 1 - 21 out of 1,153 listings
Consumer Reviews for the Toyota Highlander
Read recent reviews for the Toyota Highlander
Peppy with no lag.
Sliderule43, 04/27/2024
2024 Toyota Highlander
I went from the 2021 Venza Limited to the 2024 Highlander limited gas turbo.
The gas turbo with the 8 speed transmission is much more enjoyable to drive than the Venza hybrid. Used primarily for light traffic city driving, the turbo has no noticeable lag and is quiet. Possibly, having the Limited accounts for it being so quiet. My typical daily drive is 3.5 miles. At morning start up, … get 18 mpg, as the start up, then waiting for the screen to load, and backing out of my garage reduces mpg. Get 22 mpg on the return home. Got 24 mpg on a combo drive of 50% city and 50% rural road.
The screen is much improved over the 2021 Venza screen.
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