Used Toyota Highlander for Sale in Chicago, IL
Buy a versatile Toyota Highlander in the Windy City
Skip to FiltersReport abuse
886 listings
- $28,700great price$4,662 below market
- 52,740 miles
- 2 accidents, 1 owner, rental vehicle
- 6cyl automatic
- Kingdom Chevrolet (8 mi away)
- Home delivery*
Close
Located in Chicago, IL / 8 miles away from Chicago, IL
Priced below KBB Fair Purchase Price! CARFAX One-Owner. 2021 4D Sport Utility Toyota Highlander XLE Black 8-Speed Automatic AWD 3.5L V6 DOHC HUGE INVE...
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: 5TDGZRBH5MS549112
Stock: P24490
Certified Pre-Owned: No
Listed since: 12-04-2024 - Price Drop$37,850good price$892 below market
- 45,850 miles
- No accidents, 2 owners, personal use
- 6cyl automatic
- Zeigler Chevrolet Schaumburg (24 mi away)
Close
Located in Schaumburg, IL / 24 miles away from Chicago, IL
2022 Toyota Highlander XSE AWD. Celestial Silver MetallicAWD, 3.003 Axle Ratio, 3rd row seats: split-bench, 4-Wheel Disc Brakes, 6 Speakers, ABS bra...
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: 5TDLZRBHXNS235438
Stock: P1075
Certified Pre-Owned: No
Listed since: 03-17-2025 - Price Drop$34,850fair price$248 above market
- 18,938 miles
- No accidents, 3 owners, corporate fleet vehicle
- 4cyl automatic
- Zeigler Chevrolet Schaumburg (24 mi away)
Close
Located in Schaumburg, IL / 24 miles away from Chicago, IL
2023 Toyota Highlander L Black18" Painted Alloy Wheels, 3.329 Axle Ratio, 3rd row seats: split-bench, 4-Wheel Disc Brakes, 6 Speakers, ABS brakes, A...
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: 5TDKDRAH9PS001788
Stock: P1101
Certified Pre-Owned: No
Listed since: 03-20-2025 - New Listing$27,995fair price$520 above market
- 64,486 miles
- No accidents, 2 owners, corporate fleet vehicle
- 6cyl automatic
- High Quality Auto Sales (6 mi away)
Close
Located in Chicago, IL / 6 miles away from Chicago, IL
Visit High Quality Auto Sales online at highqualityonline.com to see more pictures of this vehicle or call us at 773-675-1370 today to schedule your ...
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: 5TDJZRFH1JS899171
Stock: 13713
Certified Pre-Owned: No - Price Drop$20,800good price$1,069 below market
- 110,077 miles
- No accidents, 1 owner, personal use only
- 6cyl automatic
- Wilkins Mazda (16 mi away)
Close
Located in Elmhurst, IL / 16 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: 5TDJZRFH2HS430391
Stock: M16268A
Certified Pre-Owned: No
Listed since: 04-07-2025 - $43,056good price$1,425 below market
- 25,017 miles
- No accidents, 1 owner, personal use only
- 4cyl automatic
- Hertz Car Sales Des Plaines (16 mi away)
Close
Located in Des Plaines, IL / 16 miles away from Chicago, IL
At Hertz Car Sales, view our thousands of vehicles with pricing often below market value! Take advantage of no-haggle pricing, our 7 day/250 mile Buy ...
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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH5RS537995
Stock: 58739
Certified Pre-Owned: No
Listed since: 02-03-2025 - Price Drop$37,000fair price$354 below market
- 23,250 miles
- No accidents, 1 owner, personal use
- 6cyl automatic
- BMW of Orland Park (24 mi away)
Close
Located in Orland Park, IL / 24 miles away from Chicago, IL
2022 Toyota Highlander XLE Odometer is 13981 miles below market average! 3RD ROW SEAT, ACTIVE BLIND SPOT DETECTION, APPLE CARPLAY COMPATIBILITY, FOLD ...
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: 5TDGZRBH3NS179408
Stock: 8799X
Certified Pre-Owned: No
Listed since: 02-24-2025 - $34,500good price$1,729 below market
- 46,750 miles
- No accidents, 1 owner, rental vehicle
- 6cyl automatic
- Al Piemonte Nissan (12 mi away)
Close
Located in Melrose Park, IL / 12 miles away from Chicago, IL
Dark Gray 2022 Toyota Highlander XLE AWD 8-Speed Automatic 3.5L V6 DOHC CARFAX CERTIFIED, RECENTLY SERVICED, COME ON AND TAKE A L@@K !!, SAVE THOUSAND...
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: 5TDHZRBH7NS246189
Stock: N14433
Certified Pre-Owned: No
Listed since: 12-17-2024 - Price Drop$25,239fair price$462 below market
- 82,915 miles
- No accidents, 2 owners, personal use
- 6cyl automatic
- Zeigler Chevrolet Schaumburg (24 mi away)
Close
Located in Schaumburg, IL / 24 miles away from Chicago, IL
2020 Toyota Highlander L AWD. Midnight Black MetallicAWD, 18" Painted Alloy Wheels, 3.003 Axle Ratio, 3rd row seats: split-bench, 4-Wheel Disc Brake...
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: 5TDCZRBH5LS033264
Stock: S10336A
Certified Pre-Owned: No
Listed since: 03-28-2025 - $19,800good price$1,112 below market
- 107,711 miles
- No accidents, 3 owners, corporate fleet vehicle
- 4cyl automatic
- Napletons River Oaks Honda (21 mi away)
- Home delivery*
Close
Located in Lansing, IL / 21 miles away from Chicago, IL
2019 Toyota Highlander LE Blizzard Pearl***PASSED RIGOROUS SAFETY INSPECTION BY ONE OF OUR CERTIFIED TECHNICIANS *** METICULOUSLY DETAILED INSIDE AND ...
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/24 Highway)
Listing Information:
VIN: 5TDZARFH3KS044189
Stock: N13191A
Certified Pre-Owned: No
Listed since: 04-04-2025 - $43,160fair price$837 above market
- 32,047 miles
- No accidents, 1 owner, rental vehicle
- 4cyl automatic
- Hertz Car Sales Des Plaines (16 mi away)
Close
Located in Des Plaines, IL / 16 miles away from Chicago, IL
At Hertz Car Sales, view our thousands of vehicles with pricing often below market value! Take advantage of no-haggle pricing, our 7 day/250 mile Buy ...
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: Yes
Features and Specs:
24 Combined MPG (21 City/28 Highway)
Listing Information:
VIN: 5TDKDRBH9RS544348
Stock: 59205
Certified Pre-Owned: No
Listed since: 03-21-2025 - Price Drop$18,643good price$1,096 below market
- 101,572 miles
- 2 accidents, 1 owner, personal use only
- 6cyl automatic
- Napleton Honda Morton Grove (14 mi away)
Close
Located in Morton Grove, IL / 14 miles away from Chicago, IL
One owner car, Great service records, take another look, Local trade-in, Nonsmoker's car, Navigation System.Buy the Napleton way! Your business is ...
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: 5TDJKRFH3FS138282
Stock: H64753A
Certified Pre-Owned: No
Listed since: 01-31-2025 - $37,550fair price$106 below market
- 30,436 miles
- No accidents, 1 owner, personal use
- 6cyl automatic
- Rizza Buick GMC (22 mi away)
- Home delivery*
Close
Located in Tinley Park, IL / 22 miles away from Chicago, IL
CARFAX One-Owner. Clean CARFAX. Local trade-in, Low Miles, AWD, 6 Speakers, Apple CarPlay/Android Auto, Exterior Parking Camera Rear, Front dual zone ...
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: 5TDGZRBH7NS577849
Stock: 23721T
Certified Pre-Owned: No
Listed since: 04-05-2025 - $34,999good price$1,998 below market
- 29,859 miles
- 1 accident, 1 owner, personal use
- 6cyl automatic
- Honda on Grand (17 mi away)
Close
Located in Elmhurst, IL / 17 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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDHZRBHXNS566154
Stock: 50421A
Certified Pre-Owned: No
Listed since: 01-14-2025 - New Listing
- 12,533 miles
- No accidents, 1 owner, personal use only
- 4cyl automatic
- CarMax Hillside (Eisenhower Expy) (14 mi away)
Close
Located in Hillside, IL / 14 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: 5TDKDRBH2PS025011
Stock: 26943950
Certified Pre-Owned: No - New Listing
- 44,797 miles
- Frame damage reported, 2 owners, corporate fleet vehicle
- 4cyl automatic
- High Quality Auto Sales (6 mi away)
Close
Located in Chicago, IL / 6 miles away from Chicago, IL
Visit High Quality Auto Sales online at highqualityonline.com to see more pictures of this vehicle or call us at 773-675-1370 today to schedule your ...
AutoCheck Vehicle History Summary
Accident Free Vehicle: No
Personal Use Only: No
History Provider: AutoCheck
Title Details: Issue reported
Salvage Vehicle: No
Frame Damage: Yes
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
24 Combined MPG (21 City/28 Highway)
Listing Information:
VIN: 5TDKDRBH8PS037843
Stock: 13693
Certified Pre-Owned: No - New Listing
- 118,931 miles
- No accidents, 3 owners, personal use
- 6cyl automatic
- CarMax Hillside (Eisenhower Expy) (14 mi away)
Close
Located in Hillside, IL / 14 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:
19 Combined MPG (17 City/22 Highway)
Listing Information:
VIN: 5TDDK3EH9DS260539
Stock: 26712784
Certified Pre-Owned: No - Price Drop$23,000fair price$526 above market
- 95,503 miles
- No accidents, 3 owners, personal use only
- 6cyl automatic
- Ed Napleton's Kia Of Elmhurst (17 mi away)
- Home delivery*
Close
Located in Elmhurst, IL / 17 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: 5TDJZRFH2HS484225
Stock: A24900B
Certified Pre-Owned: No
Listed since: 04-08-2025 - 30,135 miles
- No accidents, 1 owner, rental vehicle
- 4cyl automatic
- Al Piemonte Nissan (12 mi away)
Close
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- 106,727 miles
- No accidents, 4 owners, personal use only
- 6cyl automatic
- CarMax Tinley Park (25 mi away)
Close
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:
20 Combined MPG (18 City/24 Highway)
Listing Information:
VIN: 5TDDKRFH0FS219463
Stock: 26715035
Certified Pre-Owned: No- 26,830 miles
- No accidents, 1 owner, personal use
- 6cyl automatic
- Orland Toyota (22 mi away)
Close
Located in Tinley Park, IL / 22 miles away from Chicago, IL
2021 Toyota Highlander LE **LIKE NEW, **TOYOTA CERTIFIED, **BLACK BEAUTY, **MILES ONLY 26830, **1 OWNER CLEAN CARFAX, **BLUETOOTH, **CLOTH SEATS, **RE...
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: 5TDBZRBH2MS153018
Stock: P9858
Certified Pre-Owned: Yes
Listed since: 03-13-2025
Showing 1 - 21 out of 886 listings
Consumer Reviews for the Toyota Highlander
Read recent reviews for the Toyota Highlander
4 cylinder turbo
cousin brucie, 12/06/2023
2024 Toyota Highlander
This engine is an atkinson cycle turbo , a rare find, if you hit the gas hard it downshifts causing the engine to lug. it is in too low of a gear . that is not how you drive a turbo. Lightly give gas to get to gear 2 and then give it gas and it blows away the old six, which i just turned in . let the revs go to just below 1500 and turbo waste gate opens ( full air flow )and atkinson … cycle engages and i can get 30 to 40 mpg easy ,especially beloe 40mph . Also at 65mph not 70 hit cruise control and an easy 35+ mpg once the revs drop to atkinson cycle. If you drive correctly and use atkinson cycle correctly you can get great gas mileage and power. I had to sell my new 2024 honda crv hybrid because it was the loudest road and tire noise of any suv i ever had , no insulation i checked.. you are driving a lexus basically and it has the same insulation as lexus check the under body. I dont need 20 inch bumpy wheels 18in with high aspect rubber is great ride.The trick is to use cruise control more often this drops engine off turbo and into atkinson cycle. I dont need 3rd row ,perfect car for me i have had 5 in a row every 3 years leased.
Filters
Skip to ResultsApplied Filters4Active
Make & Model
Year
New / Used
Price & Payments
Price Rating
Body Type
Trim
Mileage
Accidents & History
Engine & Drivetrain
Exterior Color
Interior Color
Total Seating
Edmunds Review
Features
Options & Packages
MPG
* Delivery of any kind does not apply to Alaska and Hawaii. Contact the dealer for delivery details, restrictions and costs.