Used Toyota Highlander for Sale Under $40,000 NearChicago, IL
312 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- 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:
- Gray
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 42,518
- Stock #:
- P3009
- VIN:
- 5TDGZRBH8MS528223
Sponsored by Toyota of Fox Lake
2021 Toyota Highlander
XLE AWD
42,518 mi
Fox Lake, IL
45 mi away
Good Deal
$31,850
- Year:
- 2013
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Exterior color:
- Black
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- 5-Speed Automatic Overdrive
- Mileage:
- 160,079
- Stock #:
- PS101714A
- VIN:
- 5TDDK3EH4DS220420
Price drop
-$1,060
Sponsored Listing
2013 Toyota Highlander
Limited AWD
160,079 mi
Palatine, IL
28 mi away
Good Deal
$14,374
$13,314
- 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:
- Silver
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 38,110
- Stock #:
- 62221
- VIN:
- 5TDKDRAH3SS555787
Price drop
-$1,981
Sponsored Listing
2025 Toyota Highlander
LE FWD
38,110 mi
Des Plaines, IL
16 mi away
Good Deal
$34,598
$32,995
- 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:
- Jade Metallic
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Almond
- Transmission:
- 8-Speed Automatic
- Mileage:
- 96,106
- Stock #:
- 26216-1
- VIN:
- 5TDJZRFHXJS870722
New arrival
2018 Toyota Highlander
XLE AWD
96,106 mi
North Aurora, IL
39 mi away
Good Deal
$22,328
- 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:
- Magnetic Gray Metallic
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 66,508
- Stock #:
- V5993A
- VIN:
- 5TDGZRBH7MS076085
New arrival
2021 Toyota Highlander
XLE AWD
66,508 mi
Oak Park, IL
9 mi away
Good Deal
$29,995
- 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:
- Ooh La La Rouge Mica
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 103,028
- Stock #:
- P6279
- VIN:
- 5TDJZRFH4KS707792
2019 Toyota Highlander
XLE AWD
103,028 mi
Elmhurst, IL
17 mi away
Fair Deal
$23,838
- 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:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 17,615
- Stock #:
- P6513
- VIN:
- 5TDKDRBH9PS522377
New arrival
2023 Toyota Highlander
XLE AWD
17,615 mi
Chicago, IL
7 mi away
Good Deal
$38,365
- 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:
- Bronze
- Fuel type:
- Gasoline
- Interior color:
- Ash
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 145,565
- Stock #:
- CK609
- VIN:
- 5TDJKRFH9GS347737
2016 Toyota Highlander
XLE AWD
145,565 mi
Chesterton, IN
36 mi away
Fair Deal
$16,561
- 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:
- Celestial Silver Metallic
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 96,355
- Stock #:
- P4332A
- VIN:
- 5TDGZRBH2LS505146
2020 Toyota Highlander
XLE AWD
96,355 mi
Gurnee, IL
39 mi away
Fair Deal
$25,965
- 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:
- Magnetic Gray Metallic
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 49,277
- Stock #:
- CS39847B
- VIN:
- 5TDBZRBH1MS091305
New arrival
2021 Toyota Highlander
LE AWD
49,277 mi
Countryside, IL
15 mi away
Fair Deal
$29,388
- 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:
- Silver
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 128,281
- Stock #:
- 28866685
- VIN:
- 5TDLZRBH7MS073296
2021 Toyota Highlander
XSE AWD
128,281 mi
Store transfer to Oak Lawn, IL
Price includes $399 shipping
Fair Deal
$26,397
- Year:
- 2017
- 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:
- Ash
- Transmission:
- 8-Speed Automatic
- Mileage:
- 86,711
- Stock #:
- 088487BT
- VIN:
- 5TDBZRFH0HS457190
New arrival
2017 Toyota Highlander
LE Plus AWD
86,711 mi
Highland, IN
25 mi away
Fair Deal
$20,859
- 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
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 32,630
- Stock #:
- F44528A
- VIN:
- 5TDBZRFH3JS488987
New arrival
2018 Toyota Highlander
LE Plus AWD
32,630 mi
Glenview, IL
17 mi away
Good Deal
$27,123
- 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:
- Silver
- Combined gas mileage:
- 21 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 86,326
- Stock #:
- 904317A
- VIN:
- 5TDDKRFH9GS328280
2016 Toyota Highlander
Limited AWD
86,326 mi
Palatine, IL
28 mi away
Great Deal
$21,405
- 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:
- Silver Sky Metallic
- Fuel type:
- Gasoline
- Interior color:
- Ash
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 105,107
- Stock #:
- PHL3219A
- VIN:
- 5TDDKRFH3ES025671
2014 Toyota Highlander
Limited AWD
105,107 mi
Barrington, IL
31 mi away
Good Deal
$17,912
- Year:
- 2021
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- Automatic
- Mileage:
- 109,956
- Stock #:
- S20220B
- VIN:
- 5TDGZRBH8MS101351
2021 Toyota Highlander
XLE AWD
109,956 mi
Kenosha, WI
50 mi away
Good Deal
$26,246
- 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:
- White (Blizzard Pearl)
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Brown (Beige)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 55,464
- Stock #:
- XBP8712
- VIN:
- 5TDDZRBH2LS013493
New arrival
2020 Toyota Highlander
Limited AWD
55,464 mi
Libertyville, IL
30 mi away
Good Deal
$33,049
- 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:
- Midnight Black Metallic
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray (Graphite)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 121,590
- VIN:
- 5TDGZRBH5MS106846
New arrival
2021 Toyota Highlander
XLE AWD
121,590 mi
Elgin, IL
35 mi away
Great Deal
$23,363
- 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:
- Celestial Silver Metallic
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 67,041
- Stock #:
- S24952A
- VIN:
- 5TDGZRBH6MS143629
2021 Toyota Highlander
XLE AWD
67,041 mi
St. Charles, IL
32 mi away
Good Deal
$29,408
- 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
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 85,199
- Stock #:
- P9573A
- VIN:
- 5TDBZRFH1JS810400
New arrival
2018 Toyota Highlander
LE Plus AWD
85,199 mi
Crystal Lake, IL
45 mi away
Good Deal
$21,411
- 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:
- Blue
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 45,410
- Stock #:
- 28576626
- VIN:
- 5TDKDRBH8PS032058
2023 Toyota Highlander
XLE AWD
45,410 mi
Store transfer to Oak Lawn, IL
Free shipping to Oak Lawn, IL
Good Deal
$35,998
- 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:
- Gray
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- Automatic
- Mileage:
- 70,920
- Stock #:
- B49926A
- VIN:
- 5TDJZRBH6MS058294
2021 Toyota Highlander
XSE AWD
70,920 mi
Chicago, IL
1 mi away
Great Deal
$29,901
- 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:
- Celestial Silver Metallic
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 98,091
- Stock #:
- 24514T
- VIN:
- 5TDHZRBH9LS514530
2020 Toyota Highlander
XLE AWD
98,091 mi
Tinley Park, IL
22 mi away
Fair Deal
$27,647
- 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:
- Magnetic Gray Metallic
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 70,129
- Stock #:
- 50859A
- VIN:
- 5TDHZRBH3MS528795
Price drop
-$926
Sponsored Listing
2021 Toyota Highlander
XLE AWD
70,129 mi
Tinley Park, IL
22 mi away
Good Deal
$30,272
$29,346
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