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Used 2020 Toyota Highlander for Sale near Chicago, IL

197 results
Chicago, IL
2021 Toyota Highlander XLE AWD Baha Auto Group - Palos Hills

2021 Toyota Highlander

XLE AWD

107,222 miles

$24,995

Fair Deal
Palos Hills, IL
16 mi away
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:
Blueprint
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Brown (Harvest Beige)
Transmission:
Automatic
Mileage:
107,222
Stock number:
S32519
VIN:
5TDHZRBH1MS537169

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2020 Toyota Highlander XLE AWD

2020 Toyota Highlander

XLE AWD

81,474 miles

$26,999

Fair Deal
Morton Grove, IL
14 mi away
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:
Gray
Transmission:
Automatic
Mileage:
81,474
Stock number:
PM3261
VIN:
5TDGZRBH7LS514697

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2020 Toyota Highlander Limited AWD

2020 Toyota Highlander

Limited AWD

56,649 miles

$29,705

Good Deal
Libertyville, IL
30 mi away
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:
Moon Dust
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
56,649
Stock number:
XBP8214
VIN:
5TDDZRBH3LS050777

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2019 Toyota Highlander XLE AWD

2019 Toyota Highlander

XLE AWD

109,484 miles

$20,456

Great Deal
Joliet, IL
37 mi away
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:
Celestial Silver Metallic
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
109,484
Stock number:
S251183A
VIN:
5TDJZRFH5KS582706

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2019 Toyota Highlander

LE AWD

62,910 miles

$20,999

Great Deal
Villa Park, IL
18 mi away
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:
Gray
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
Automatic
Mileage:
62,910
Stock number:
P0392
VIN:
5TDBZRFH4KS740392

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2019 Toyota Highlander

SE AWD

66,734 miles

$24,848

Great Deal
Fox Lake, IL
45 mi away
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:
Automatic
Mileage:
66,734
Stock number:
P2742
VIN:
5TDJZRFHXKS570034

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2021 Toyota Highlander

XSE AWD

70,497 miles

$29,499

Good Deal
Lake Villa, IL
43 mi away
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:
Automatic
Mileage:
70,497
Stock number:
LV565
VIN:
5TDLZRBH2MS147269

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2021 Toyota Highlander

XSE AWD

80,354 miles

$30,000

Fair Deal
Kenosha, WI
49 mi away
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:
Black (Charcoal)
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
80,354
Stock number:
M25529A
VIN:
5TDJZRBH7MS149011

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2021 Toyota Highlander

LE AWD

102,633 miles

$20,995

Great Deal
Cicero, IL
6 mi away
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:
102,633
Stock number:
N23037
VIN:
5TDBZRBH7MS540485

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2019 Toyota Highlander

XLE AWD

92,303 miles

$21,111

Great Deal
Huntley, IL
45 mi away
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:
Predawn Gray Mica
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Transmission:
8-Speed Automatic
Mileage:
92,303
Stock number:
V2557A
VIN:
5TDJZRFH9KS578609

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2019 Toyota Highlander

42,916 miles

$29,300

Fair Deal
Kenosha, WI
50 mi away
Year:
2019
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Engine:
295 hp 3.5L V6
Exterior color:
White
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
42,916
Stock number:
P4710
VIN:
5TDJZRFH7KS998773

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2021 Toyota Highlander

XSE FWD

85,105 miles

$27,397

Good Deal
Store transfer to Oak Lawn, IL
1,238 mi away • Price includes $1,399 shipping Price includes $1,399 shipping
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:
Black
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Red
Transmission:
Automatic
Mileage:
85,105
Stock number:
28112203
VIN:
5TDLZRAH2MS059159

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2019 Toyota Highlander

Limited AWD

82,431 miles

$25,495

Great Deal
Certified Pre-Owned
Libertyville, IL
31 mi away
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:
Almond
Transmission:
Automatic
Mileage:
82,431
Stock number:
KS707496
VIN:
5TDDZRFH4KS707496

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2019 Toyota Highlander

SE AWD

136,133 miles

$19,980

Fair Deal
Palatine, IL
28 mi away
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:
Predawn Gray Mica
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Interior color:
Almond
Transmission:
8-Speed Automatic
Mileage:
136,133
Stock number:
PS100935A
VIN:
5TDJZRFH4KS939891

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2021 Toyota Highlander

Platinum AWD

72,506 miles

$34,756

Fair Deal
Fox Lake, IL
45 mi away
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:
72,506
Stock number:
P2773
VIN:
5TDFZRBH3MS142403

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  1. Home
  2. / Used Cars
  3. / Toyota Highlander
  4. / 2020
  5. / Illinois
  6. / Chicago
Overview
Reviews
FAQs

CarGurus Analysis: 2020 Toyota Highlander

Picture of 2020 Toyota Highlander

Summary

  • With 3,587 currently listed for sale on CarGurus and an average price of $27,857.10, 35.7% of 2020 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
  • Favorably reviewed: Owners rated the 2020 Toyota Highlander 4.5 / 5 stars and CarGurus experts gave it an 7.7 / 10.
  • 73% of 2020 Highlander models on CarGurus are accident free.
  • The 2020 Toyota Highlander excelled in passenger comfort with its tranquil interior, soft ride, and advanced safety features, making it a top choice in the midsize SUV segment.

Why it stands out

The 2020 Toyota Highlander distinguished itself with a premium feel that rivaled luxury vehicles like Lexus, especially in its upper trims. It provided a remarkably quiet and smooth ride, enhancing passenger comfort across all three rows. Additionally, the Highlander came equipped with standard advanced safety features, making it a practical choice for families seeking both space and peace of mind.

Other model years to consider

  • 2022 Toyota Highlander: This year offers $33,572.41 average price, 36% good/great deals, 4.6/5 user rating, 8.2/10 expert rating, 6,308 listings.
  • 2021 Toyota Highlander: This year offers $30,215.79 average price, 36% good/great deals, 4.8/5 user rating, 7.5/10 expert rating, 4,417 listings.
  • 2023 Toyota Highlander: This year offers $35,244.49 average price, 35% good/great deals, 4.4/5 user rating, 6,084 listings.

This analysis is based on CarGurus' proprietary market data from December 16, 2025, CarGurus experts' opinions, and generative AI.

4.5 Overall rating

(33 reviews)
Karen D
4.0
Reviewed a 2020 Toyota Highlander on Mar 11, 2024

The 2020 Toyota Highlander XLE drives great!! Very smooth ride and great acceleration. I loved how it could turn tight corners, like when pulling out onto a 4-lane road. A lot of great features. The sound system was ok, but realized it wasnt that great after comparing it to the 2021 Limited with JBL speakers. Wish it had the nicer sound system. There were two things I was very disappointed in. The seats seemed rather shallow, compared to the seats in my 2012 Limited Highlander. My friend and I both felt like we were sliding off the edge of the front seats. Does Toyota think that Americans are getting smaller? The other thing was that the visors were not long enough to come all the way out to the edge of the windshield. There was at least a two inch gap between the outside edge of the visor and the outside edge of the windshield!! What the heck were they thinking! Driving toward the sun in the late afternoon was terrible because the sun was in my eyes and there was nothing I could do about it. Again, my 2012 Highlander has this one beat because the visor is plenty long enough. What a stupid place to try to save a buck! Those two things have me looking at other vehicles because I dont want to settle for something that is uncomfortable, and when you pay 40K for a vehicle, it better be good in every aspect!

Anonymous
5.0
Reviewed a 2020 Toyota Highlander on Nov 07, 2020

Most comfortable riding vehicle that we have ever purchased. Great features and a great looking vehicle as well.

Kris B
5.0
Reviewed a 2020 Toyota Highlander on May 22, 2023

Absolutely love this car. Great comfortable family vehicle with plenty of space, and features

Lee W
4.0
Reviewed a 2020 Toyota Highlander on Feb 27, 2020

The ride was smooth, the Highlander is quick and very quiet. I loved many of the features it had, like the posted speed limit on the instrument cluster. What really disappointed me was the passenger seat comfort. The seat bottom only adjusts fron-to-rear, not up or down so I wasn’t as comfortable in it as I was the Hyundai Palisade or the Kia Telluride. It’s still a really good vehicle.

Becky S
5.0
Reviewed a 2020 Toyota Highlander on Nov 22, 2022

Just picked one up Saturday! Absolutely love it, love the features, everything about it. Love the 3 row seats for all the grandkids. Had a Lexus RX350, feel there very similar just a little more room in the Highlander. Levy’s very smooth driving though.

2020 Toyota Highlander FAQs

How much does the 2020 Toyota Highlander cost in Chicago, IL?

The average 2020 Toyota Highlander costs about $27,142.73. The average price has decreased by -8.1% since last year. The 197 for sale near Chicago, IL on CarGurus, range from $15,363 to $48,902 in price.

Is the 2020 Toyota Highlander a good car?

CarGurus experts gave the 2020 Toyota Highlander an overall rating of 7.7/10 and 2020 Toyota Highlander owners have rated the vehicle a 4.5/5 stars on average. If a vehicle has both strong expert and owner reviews, you can feel confident in its quality. If either expert reviews, owner reviews, or both are spotty, you might want to do some research to figure out where the car falls short.

How many 2020 Toyota Highlander vehicles in Chicago, IL have no reported accidents or damage?

196 out of 197 for sale near Chicago, IL have no reported accidents or damage.

Is the 2020 Toyota Highlander safe?

CarGurus experts gave the 2020 Toyota Highlander a safety rating of 9/10.

What is the fuel economy of the 2020 Toyota Highlander?

Depending on the engine and options, the 2020 Toyota Highlander gets between 22 and 23 MPG (or EV battery range).

What fuel types are available?

Gasoline engines are available.

  • 2023 Toyota Highlander in Chicago IL

  • 2022 Toyota Highlander in Chicago IL

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