Used 2021 Toyota Highlander for Sale nearChicago, IL

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244 vehicles found

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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
Pearl 2022 Toyota Highlander SUV / Crossover Front-Wheel Drive 8-Speed Automatic
Zeigler Ford of North Riverside

Sponsored by Zeigler Ford of North Riverside

2022 Toyota Highlander

XLE FWD

46,311 mi

Riverside, IL
9 mi away
Fair Deal

$34,434

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:
Midnight Black Metallic
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
68,307
Stock #:
Z2900A
VIN:
5TDDZRBHXLS001544
Midnight Black Metallic 2020 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic
Price drop

-$3,797

Sponsored Listing

2020 Toyota Highlander

Limited AWD

68,307 mi

Skokie, IL
14 mi away
Good Deal

$35,317

$31,520

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:
Blue
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
Automatic
Mileage:
61,993
Stock #:
70136785
VIN:
5TDDZRBH4MS107862
Blue 2021 Toyota Highlander SUV / Crossover All-Wheel Drive Automatic
Price drop

-$1,000

 

2021 Toyota Highlander

Limited AWD

61,993 mi

Algonquin, IL
41 mi away
Fair Deal

$34,998

$33,998

Year:
2020
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Moon Dust
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
101,101
Stock #:
AC260
VIN:
5TDGZRAH9LS015546
Moon Dust 2020 Toyota Highlander SUV / Crossover Front-Wheel Drive 8-Speed Automatic

 

2020 Toyota Highlander

XLE FWD

101,101 mi

Home delivery from Arab, AL
Price includes $789 shipping
Good Deal

$25,188

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:
Magnetic Gray Metallic
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
91,310
Stock #:
PB5282
VIN:
5TDGZRBH7NS586177
Magnetic Gray Metallic 2022 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic
Price drop

-$2,197

 

2022 Toyota Highlander

XLE AWD

91,310 mi

Home delivery from Frankfort, KY
Price includes $436 shipping
Great Deal

$28,936

$27,738

CarGurus Analysis:

2021 Toyota Highlander

4.9

  • With 242 currently listed for sale near Chicago, IL and an average price of $30,563.00, 36.8% of 2021 Toyota Highlanders for sale on CarGurus are rated as good or great deals.

  • Favorably reviewed: Owners rated the 2021 Toyota Highlander 4.86 / 5 stars and CarGurus experts gave it a 7.5 / 10.

  • 100.0% of 2021 Highlander models on CarGurus are accident free.

Research summarized using AI

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:
89,930
Stock #:
29142
VIN:
5TDCZRBHXMS530280
Celestial Silver Metallic 2021 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic

 

2021 Toyota Highlander

L AWD

89,930 mi

Home delivery from Cambridge, OH
Price includes $508 shipping
Great Deal

$23,086

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:
Moon Dust
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
52,785
Stock #:
H0045A
VIN:
5TDGZRBH8MS156091
Moon Dust 2021 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic
Price drop

-$1,079

 

2021 Toyota Highlander

XLE AWD

52,785 mi

Lincolnwood, IL
10 mi away
Great Deal

$28,373

$27,294

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:
Moon Dust
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
91,466
Stock #:
NP12576
VIN:
5TDFZRBH1MS057446
Moon Dust 2021 Toyota Highlander SUV / Crossover All-Wheel Drive 8-Speed Automatic

 

2021 Toyota Highlander

Platinum AWD

91,466 mi

Home delivery from Indianapolis, IN
Price includes $350 shipping
Fair Deal

$30,750

Year:
2022
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
295 hp 3.5L V6
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
67,106
Stock #:
GM6740A
VIN:
5TDGZRAH5NS135802
 2022 Toyota Highlander SUV / Crossover Front-Wheel Drive Automatic

 

2022 Toyota Highlander

XLE FWD

67,106 mi

Niles, IL
16 mi away
Fair Deal

$31,191

CarGurus Analysis: 2021 Toyota Highlander

7.5
of 10
overall
Look and feel8/10
Technology7/10
Performance6/10
Safety10/10
Form & function7/10
Cost effectiveness7/10
Image Not Available

Summary

  • With 242 currently listed for sale near Chicago, IL and an average price of $30,563.00, 36.8% of 2021 Toyota Highlanders for sale on CarGurus are rated as good or great deals.

  • Favorably reviewed: Owners rated the 2021 Toyota Highlander 4.86 / 5 stars and CarGurus experts gave it a 7.5 / 10.

  • 100.0% of 2021 Highlander models on CarGurus are accident free.

Why it stands out

The 2021 Toyota Highlander stands out as a familiar three-row family SUV that leans heavily on comfort and safety. It already sits near the top of the sales charts for its segment, and the Highlander name carries strong recognition as it enters its 20th year of production. For 2021, Toyota adds additional safety-feature technology as standard equipment, reinforcing the Highlander’s appeal to buyers who want a practical family vehicle with a reassuring feature set.

Behind that straightforward mission, the Highlander’s strengths are easy to understand: it offers a great ride quality, a comfortable cabin, and plenty of space. Those qualities make it especially appealing for families who value everyday usability over flash. At the same time, it is not the most exciting choice in the class. Its styling is uninspired, the base engine is underwhelming, and its technology is described as outdated, so shoppers looking for the latest performance or infotainment polish may find it less compelling than its core virtues suggest.

Owner feedback generally reinforces that picture. Drivers commonly praise the 2021 Toyota Highlander for its comfort, reliability, smooth ride, high-quality interior, spaciousness, and safety features. Some, however, have been disappointed by fuel economy and by limited configurability for certain settings, including the third-row seating and lane assist functions.

Other model years to consider

  • 2024 Toyota Highlander

    • Average price: $38,796.00
    • Good/great deal percentage: 49.3%
    • User rating: 5 / 5
    • Total listings: 209
  • 2023 Toyota Highlander

    • Average price: $33,633.00
    • Good/great deal percentage: 51.4%
    • User rating: 4.75 / 5
    • Total listings: 255
  • 2022 Toyota Highlander

    • Average price: $33,656.00
    • Good/great deal percentage: 43.7%
    • User rating: 4.5 / 5
    • Total listings: 316

This analysis is based on CarGurus' proprietary market data from August 11, 2026, CarGurus experts' opinions, and generative AI.

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