Used Toyota Highlander for Sale with Tow Package inChicago, IL
85 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- Year:
- 2025
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- White (Wind Chill Pearl)
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Transmission:
- 8-Speed Automatic
- Mileage:
- 10,383
- Stock #:
- TR43791
- VIN:
- 5TDKDRBH5SS590961
New arrival
Sponsored by McGrath Elmhurst Toyota
2025 Toyota Highlander
XLE AWD
10,383 mi
Elmhurst, IL
17 mi away
Fair Deal
$47,366
- Year:
- 2021
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Silver
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- Automatic
- Mileage:
- 89,272
- Stock #:
- 4171
- VIN:
- 5TDGZRAH2MS534598
Sponsored Listing
2021 Toyota Highlander
XLE FWD
89,272 mi
Arlington Heights, IL
23 mi away
Great Deal
$25,190
- Year:
- 2008
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 155,943
- Stock #:
- 82010987
- VIN:
- JTEES43A282010987
Sponsored Listing
2008 Toyota Highlander
Sport 4WD
155,943 mi
Des Plaines, IL
16 mi away
Fair Deal
$9,377
- Year:
- 2018
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Celestial Silver Metallic
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black w/Silver Stitching
- Transmission:
- Automatic
- Mileage:
- 109,447
- Stock #:
- PH2084
- VIN:
- 5TDJZRFH1JS548762
Price drop
-$690
2018 Toyota Highlander
SE AWD
109,447 mi
Palos Hills, IL
16 mi away
Fair Deal
$21,968
$21,278
- Year:
- 2018
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Midnight Black Metallic
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 113,992
- Stock #:
- N23694
- VIN:
- 5TDJZRFH2JS556224
Price drop
-$795
2018 Toyota Highlander
XLE AWD
113,992 mi
Chicago, IL
6 mi away
Good Deal
$20,819
$20,024
- Year:
- 2025
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- White (Wind Chill Pearl)
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Transmission:
- 8-Speed Automatic
- Mileage:
- 10,383
- Stock #:
- TR43791
- VIN:
- 5TDKDRBH5SS590961
New arrival
2025 Toyota Highlander
XLE AWD
10,383 mi
Elmhurst, IL
17 mi away
Fair Deal
$47,366
- Year:
- 2019
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Silver
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic
- Mileage:
- 143,402
- Stock #:
- P060833
- VIN:
- 5TDZARFH7KS060833
2019 Toyota Highlander
LE FWD
143,402 mi
Home delivery from Owensboro, KY
Price includes $287 shipping
Great Deal
$15,386
- Year:
- 2025
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- White (Wind Chill Pearl)
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Transmission:
- 8-Speed Automatic
- Mileage:
- 12,560
- Stock #:
- TR43648
- VIN:
- 5TDKDRBH3SS589680
2025 Toyota Highlander
XLE AWD
12,560 mi
Elmhurst, IL
17 mi away
Good Deal
$46,366
- Year:
- 2008
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 155,943
- Stock #:
- 82010987
- VIN:
- JTEES43A282010987
2008 Toyota Highlander
Sport 4WD
155,943 mi
Des Plaines, IL
16 mi away
Fair Deal
$9,377
- Year:
- 2015
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Exterior color:
- Attitude Black Metallic
- Combined gas mileage:
- 21 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 127,347
- Stock #:
- 11257
- VIN:
- 5TDDKRFH9FS179772
2015 Toyota Highlander
Limited AWD
127,347 mi
Waukegan, IL
35 mi away
Fair Deal
$19,360
- Year:
- 2019
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Green
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 81,658
- Stock #:
- 26266
- VIN:
- 5TDDZRFH1KS708170
2019 Toyota Highlander
Limited AWD
81,658 mi
Home delivery from Saugus, MA
Price includes $1,488 shipping
Fair Deal
$29,480
- Year:
- 2019
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- White (Blizzard Pearl)
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Brown (Saddle Tan Leather)
- Transmission:
- Automatic
- Mileage:
- 91,571
- Stock #:
- 6065A
- VIN:
- 5TDDZRFH1KS936766
2019 Toyota Highlander
Limited AWD
91,571 mi
Home delivery from Godfrey, IL
Price includes $366 shipping
Good Deal
$25,365
- Year:
- 2012
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Exterior color:
- Red (Burgundy)
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- 5-Speed Automatic
- Mileage:
- 165,907
- Stock #:
- 141413PAM
- VIN:
- 5TDBK3EH9CS141413
2012 Toyota Highlander
SE AWD
165,907 mi
Home delivery from Stafford, VA
Price includes $886 shipping
Good Deal
$10,766
- Year:
- 2014
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Exterior color:
- Black
- Combined gas mileage:
- 21 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- Automatic
- Mileage:
- 170,723
- Stock #:
- VAAW1511
- VIN:
- 5TDDKRFH8ES059802
2014 Toyota Highlander
Limited AWD
170,723 mi
Home delivery from Chantilly, VA
Price includes $570 shipping
Great Deal
$13,344
- Year:
- 2018
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Gray
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 115,752
- Stock #:
- D2019
- VIN:
- 5TDJZRFH2JS556997
2018 Toyota Highlander
SE AWD
115,752 mi
Addison, IL
20 mi away
Good Deal
$20,600
- Year:
- 2012
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Exterior color:
- Cypress Pearl
- Fuel type:
- Gasoline
- Interior color:
- Brown (Beige)
- Transmission:
- 5-Speed Automatic Overdrive
- Mileage:
- 109,817
- Stock #:
- H153
- VIN:
- 5TDDK3EH9CS094702
2012 Toyota Highlander
Limited AWD
109,817 mi
Addison, IL
19 mi away
Fair Deal
$15,362
- Year:
- 2021
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Silver
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- Automatic
- Mileage:
- 89,272
- Stock #:
- 4171
- VIN:
- 5TDGZRAH2MS534598
2021 Toyota Highlander
XLE FWD
89,272 mi
Arlington Heights, IL
23 mi away
Great Deal
$25,190
- Year:
- 2020
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Silver
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- White
- Transmission:
- Automatic
- Mileage:
- 60,383
- Stock #:
- FNF001014
- VIN:
- 5TDGZRBH7LS001014
2020 Toyota Highlander
XLE AWD
60,383 mi
Home delivery from Lynnwood, WA
Price includes $1,212 shipping
Fair Deal
$31,012
- Year:
- 2018
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- White (Blizzard Pearl)
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 60,513
- Stock #:
- 10194
- VIN:
- 5TDDZRFH9JS855996
2018 Toyota Highlander
Limited AWD
60,513 mi
Buffalo Grove, IL
25 mi away
Fair Deal
$28,412
- Year:
- 2016
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Exterior color:
- Alumina Jade Metallic
- Combined gas mileage:
- 21 MPG
- Fuel type:
- Gasoline
- Interior color:
- Almond
- Transmission:
- Automatic
- Mileage:
- 96,122
- Stock #:
- 9849
- VIN:
- 5TDDKRFH7GS352478
2016 Toyota Highlander
Limited AWD
96,122 mi
Summit, IL
12 mi away
Good Deal
$21,380
- Year:
- 2013
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Exterior color:
- Cypress Pearl
- Combined gas mileage:
- 21 MPG
- Fuel type:
- Gasoline
- Interior color:
- Brown (Sand Beige)
- Transmission:
- Automatic
- Mileage:
- 204,167
- Stock #:
- E362
- VIN:
- 5TDZK3EH8DS108516
2013 Toyota Highlander
SE FWD
204,167 mi
Addison, IL
20 mi away
Fair Deal
$9,450
- Year:
- 2021
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- White (Blizzard Pearl)
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray (Graphite)
- Transmission:
- Automatic
- Mileage:
- 61,899
- Stock #:
- PC2495A
- VIN:
- 5TDGZRBH4MS072933
New arrival
2021 Toyota Highlander
XLE AWD
61,899 mi
Home delivery from Edmond, OK
Price includes $684 shipping
Fair Deal
$32,434
- Year:
- 2019
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Silver
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 97,971
- Stock #:
- EZA6251
- VIN:
- 5TDJZRFHXKS582149
2019 Toyota Highlander
XLE AWD
97,971 mi
Home delivery from Stafford, VA
Price includes $1,182 shipping
Good Deal
$24,667
- Year:
- 2024
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Midnight Black Metallic
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray (Graphite)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 14,088
- Stock #:
- 40592A
- VIN:
- 5TDKDRBH9RS534094
Sponsored Listing
2024 Toyota Highlander
Platinum AWD
14,088 mi
Crystal Lake, IL
42 mi away
Fair Deal
$50,377
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