Used Toyota Highlander for Sale with Low Mileage inChicago, IL
242 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- Year:
- 2026
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Black
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 14,771
- Stock #:
- TS605021
- VIN:
- 5TDKDRBHXTS605021
Sponsored by AutoNation Toyota Libertyville
2026 Toyota Highlander
XLE AWD
14,771 mi
Libertyville, IL
31 mi away
Good Deal
$48,798
- Year:
- 2025
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Gray
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 31,873
- Stock #:
- 62040
- VIN:
- 5TDKDRAH7SS554089
Price drop
-$1,429
Sponsored Listing
2025 Toyota Highlander
LE FWD
31,873 mi
Des Plaines, IL
16 mi away
Good Deal
$35,149
$34,098
- Year:
- 2025
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Blue
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 30,053
- Stock #:
- 62204
- VIN:
- 5TDKDRAHXSS554412
Price drop
-$1,464
Sponsored Listing
2025 Toyota Highlander
LE FWD
30,053 mi
Des Plaines, IL
16 mi away
Good Deal
$35,335
$34,249
- Year:
- 2022
- 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:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 27,337
- Stock #:
- B2244
- VIN:
- 5TDGZRBH8NS591095
New arrival
2022 Toyota Highlander
XLE AWD
27,337 mi
Home delivery from Normal, IL
Price includes $174 shipping
Good Deal
$35,910
- 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:
- Celestial Silver Metallic
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 25,104
- Stock #:
- P7352
- VIN:
- 5TDKDRBH5SS583265
2025 Toyota Highlander
XSE AWD
25,104 mi
Calumet City, IL
19 mi away
Great Deal
$39,844
- Year:
- 2023
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Pearl
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 22,595
- Stock #:
- C21111A
- VIN:
- 5TDKDRBH4PS041226
New arrival
2023 Toyota Highlander
XLE AWD
22,595 mi
Chicago, IL
7 mi away
Fair Deal
$38,565
- Year:
- 2022
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Moon Dust
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 48,063
- Stock #:
- 14798
- VIN:
- 5TDGZRBH0NS257899
2022 Toyota Highlander
XLE AWD
48,063 mi
Home delivery from Philadelphia, PA
Price includes $832 shipping
Great Deal
$33,546
- 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:
- Black
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Red
- Transmission:
- 8-Speed Automatic
- Mileage:
- 8,706
- Stock #:
- D5835L
- VIN:
- 5TDKDRBH1SS590939
New arrival
2025 Toyota Highlander
XSE AWD
8,706 mi
Home delivery from Dublin, OH
Price includes $396 shipping
Fair Deal
$45,781
- Year:
- 2022
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Pearl
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 46,311
- Stock #:
- Z5548
- VIN:
- 5TDGZRAH9NS556535
2022 Toyota Highlander
XLE FWD
46,311 mi
Riverside, IL
9 mi away
Good Deal
$33,494
- Year:
- 2024
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Midnight Black Metallic
- Combined gas mileage:
- 25 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 18,627
- Stock #:
- KC0308A
- VIN:
- 5TDKDRAH6RS531915
2024 Toyota Highlander
XSE FWD
18,627 mi
Lincolnwood, IL
10 mi away
Good Deal
$39,868
- Year:
- 2023
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Wind Chill Pearl - 089
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 47,139
- Stock #:
- PS000850T
- VIN:
- 5TDKDRBH7PS000850
2023 Toyota Highlander
XLE AWD
47,139 mi
Home delivery from Egg Harbor Township, NJ
Price includes $1,053 shipping
Good Deal
$34,352
- Year:
- 2023
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Silver
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 44,855
- Stock #:
- P20695
- VIN:
- 5TDKDRBH8PS039947
2023 Toyota Highlander
LE AWD
44,855 mi
Streamwood, IL
32 mi away
Good Deal
$30,858
- Year:
- 2023
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Magnetic Gray Metallic
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 49,411
- Stock #:
- P7323
- VIN:
- 5TDKDRBH1PS028983
2023 Toyota Highlander
XLE AWD
49,411 mi
Calumet City, IL
19 mi away
Good Deal
$34,676
- Year:
- 2022
- 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:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray (Graphite)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 46,619
- Stock #:
- BC2311
- VIN:
- 5TDBZRBH7NS594421
2022 Toyota Highlander
LE AWD
46,619 mi
North Riverside, IL
10 mi away
Fair Deal
$31,164
- 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:
- Celestial Silver Metallic
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 26,944
- Stock #:
- RS570251
- VIN:
- 5TDKDRBH3RS570251
New arrival
2024 Toyota Highlander
Limited AWD
26,944 mi
Libertyville, IL
31 mi away
Good Deal
$43,868
- Year:
- 2024
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Transmission:
- 8-Speed Automatic
- Mileage:
- 38,758
- Stock #:
- 57476900
- VIN:
- 5TDKDRBH7RS574769
2024 Toyota Highlander
XSE AWD
38,758 mi
Calumet City, IL
19 mi away
Fair Deal
$41,316
- 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
2025 Toyota Highlander
XLE AWD
10,383 mi
Elmhurst, IL
17 mi away
Fair Deal
$47,366
- 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:
- White
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Cockpit Red
- Transmission:
- 8-Speed Automatic
- Mileage:
- 38,388
- Stock #:
- MX4769
- VIN:
- 5TDKDRBH3RS548623
2024 Toyota Highlander
XSE AWD
38,388 mi
Home delivery from Louisville, TN
Price includes $828 shipping
Fair Deal
$41,527
- Year:
- 2025
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Black
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 26,011
- Stock #:
- 62028
- VIN:
- 5TDKDRAH1SS553889
Price drop
-$1,529
2025 Toyota Highlander
LE FWD
26,011 mi
Des Plaines, IL
16 mi away
Good Deal
$35,749
$34,598
- Year:
- 2023
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Silver
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 33,613
- Stock #:
- P21793
- VIN:
- 5TDKDRBH1PS002822
2023 Toyota Highlander
XSE AWD
33,613 mi
Streamwood, IL
32 mi away
Good Deal
$37,858
- Year:
- 2023
- 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:
- 47,796
- Stock #:
- X0261061A
- VIN:
- 5TDKDRBHXPS527443
2023 Toyota Highlander
Limited AWD
47,796 mi
Schaumburg, IL
25 mi away
Good Deal
$38,301
- 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:
- Ooh La La Rouge Mica
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Almond
- Transmission:
- 8-Speed Automatic
- Mileage:
- 41,326
- Stock #:
- R6405
- VIN:
- 5TDJZRFH9JS903242
2018 Toyota Highlander
XLE AWD
41,326 mi
Home delivery from Milford, OH
Price includes $388 shipping
Good Deal
$27,910
- Year:
- 2023
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Silver
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- Automatic
- Mileage:
- 34,277
- Stock #:
- P21948
- VIN:
- 5TDKDRBH1PS511082
2023 Toyota Highlander
XLE AWD
34,277 mi
Streamwood, IL
32 mi away
Good Deal
$36,858
- 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:
- 37,357
- Stock #:
- 13042P
- VIN:
- 5TDKDRBH2SS588794
Sponsored Listing
2025 Toyota Highlander
LE AWD
37,357 mi
Elmhurst, IL
17 mi away
Good Deal
$37,376
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