Used Toyota Highlander for Sale by Owner & Dealer in Chicago, IL

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2018 Toyota Highlander LE Plus

2018 Toyota Highlander LE Plus - 82,225 mi

Naperville, IL (25 mi) - Listed 85 days ago
  • $5,920 below market price
  • dealer rating
  • 11 price drops in 86 days
$28,877
PREVIEW
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2004 Toyota Highlander Limited

2004 Toyota Highlander Limited - 193,180 mi

Chicago, IL (7 mi) - Listed 4 days ago
  • $1,143 below market price
  • dealer rating
PREVIEW
iSeeCars Unbiased Insights

How can you save money on a used Toyota Highlander?

  • Highlander

    $34,400
    $7,108 Savings

    Highlander Hybrid

    $41,508
  • 4-Cylinder

    $28,590
    $4,632 Savings

    6-Cylinder

    $33,222
  • FWD

    $31,518
    $3,186 Savings

    AWD

    $34,704

iSeeCars analyzes over 25 billion data points to help you find the best deals.
See more ways to save.

iSeeCars Unbiased Insights

Does car color affect the price of a used Toyota Highlander?

Least
Expensive

Teal

$2,500Average Savings

Most
Expensive

Purple

$1,664Average Premium

iSeeCars analyzes over 25 billion data points to help you find the best deals.
See more ways to save.

2007 Toyota Highlander Base

2007 Toyota Highlander Base - 92,824 mi

Northbrook, IL (21 mi) - Listed 5 days ago
  • $1,619 below market price
  • dealer rating
  • low annual miles
PREVIEW
2004 Toyota Highlander Base

2004 Toyota Highlander Base - 227,460 mi

Chicago, IL (5 mi) - Listed 6 days ago
  • $1,137 below market price
PREVIEW
2013 Toyota Highlander Plus

2013 Toyota Highlander Plus - 103,740 mi

Elmhurst, IL (15 mi) - Listed 42 days ago
  • $3,212 below market price
  • 3 price drops in 43 days
$17,939
PREVIEW
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2017 Toyota Highlander XLE

2017 Toyota Highlander XLE - 63,424 mi

Schaumburg, IL (24 mi) - Listed 109 days ago
  • $5,591 below market price
  • dealer rating
  • low annual miles
$31,995
PREVIEW
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2007 Toyota Highlander Sport

2007 Toyota Highlander Sport - 199,715 mi

Posen, IL (15 mi) - Listed 111 days ago
  • $2,285 below market price
  • dealer rating
  • 4 price drops in 112 days
$6,999
PREVIEW
2018 Toyota Highlander LE

2018 Toyota Highlander LE - 71,380 mi

Streamwood, IL (29 mi) - Listed 146 days ago
  • $3,906 below market price
  • dealer rating
  • 1-owner
$30,990
PREVIEW
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2004 Toyota Highlander Base

2004 Toyota Highlander Base - 194,412 mi

Chicago, IL (5 mi) - Listed 61 days ago
  • $1,292 below market price
  • dealer rating
PREVIEW
2017 Toyota Highlander XLE

2017 Toyota Highlander XLE - 88,132 mi

Chicago, IL (6 mi) - Listed 103 days ago
  • $3,708 below market price
  • 10 price drops in 104 days
$30,990
PREVIEW
2019 Toyota Highlander SE

2019 Toyota Highlander SE - 68,027 mi

Saint Charles, IL (32 mi) - Listed 106 days ago
  • $4,586 below market price
  • 9 price drops in 107 days
$34,300
PREVIEW
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2013 Toyota Highlander SE

2013 Toyota Highlander SE - 175,800 mi

Wilmington, IL (46 mi) - Listed 105 days ago
  • $1,921 below market price
  • dealer rating
  • 1 price drop in 106 days
$13,995
PREVIEW
View on dealer site
2012 Toyota Highlander SE

2012 Toyota Highlander SE - 137,393 mi

Michigan City, IN (40 mi) - Listed 40 days ago
  • $1,713 below market price
  • 2 price drops in 41 days
$15,900
PREVIEW
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2016 Toyota Highlander LE

2016 Toyota Highlander LE - 60,753 mi

Huntley, IL (46 mi) - Listed 112 days ago
  • $2,386 below market price
  • dealer rating
  • low annual miles
$26,999
PREVIEW
2021 Toyota Highlander XLE

2021 Toyota Highlander XLE - 14,992 mi

Willowbrook, IL (15 mi) - Listed 57 days ago
  • $1,380 below market price
  • dealer rating
  • 1-owner, 3 positives , low annual miles
$46,928
PREVIEW
2020 Toyota Highlander L

2020 Toyota Highlander L - 5,050 mi

Chicago, IL (6 mi) - Listed 29 days ago
  • $2,240 below market price
  • dealer rating
  • 1-owner, low annual miles
PREVIEW
2017 Toyota Highlander XLE

2017 Toyota Highlander XLE - 23,549 mi

Calumet City, IL (17 mi) - Listed 41 days ago
  • $1,579 below market price
  • dealer rating
  • 1-owner, low annual miles
$35,995
PREVIEW
2015 Toyota Highlander LE Plus

2015 Toyota Highlander LE Plus - 81,239 mi

Matteson, IL (23 mi) - Listed today
  • $863 below market price
  • dealer rating
  • low annual miles
PREVIEW
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How to save money when buying a used Toyota Highlander in Chicago?

Fuel Type A Highlander averages $7,108 less than a Highlander Hybrid
Engine A 4-Cylinder Highlander costs $4,632 less than a 6-Cylinder
Drive Type A front-wheel drive (FWD) Toyota Highlander can be priced $3,186 less than an all-wheel drive (AWD)
Certified Choosing non-CPO vs Certified Pre-Owned (CPO) can save you $939 on a Toyota Highlander

Buying Tips

Average car color pricing for a used Toyota Highlander in Chicago?

Rank Color Compared to Avg Price
1 Teal $2,500 Savings
2 Gray $1,571 Savings
3 Brown $934 Savings
4 Black $659 Savings
5 Silver $493 Savings
6 White $295 Higher
7 Beige $325 Higher
8 Green $381 Higher
9 Red $669 Higher
10 Blue $1,179 Higher
11 Orange $1,398 Higher
12 Purple $1,664 Higher

What Toyota Highlander color has the best resale value in Chicago?

Price differences by car color compared to the average price of a used Toyota Highlander in Chicago

What is the best time to buy a used Toyota Highlander in Chicago?

Good times to buy
- Save $274 on average: January, September, October, November, December are good times to buy to find the best prices.
Good times to sell
- Make an extra $198 on average: February, March, April, May, June, July, August are good times to sell to get the best prices
Search for a used Toyota Highlander in Chicago
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What colors are the best deals for a Toyota Highlander in Chicago?

Least Expensive Color
Teal $2,500Average Savings
Most Expensive Color
Purple $1,664Average Premium
Total saved by iSeeCars users

$344,055,192

Start searching smarter now

Price of Used Toyota Highlander for Sale in Chicago, IL by Distance

Distance from Chicago, IL Average Price Deals Listings
50 miles
$30,497 Save $5,591 on 56 deals 281 listings
100 miles
$30,745 Save $5,591 on 110 deals 425 listings
200 miles
$30,747 Save $6,199 on 247 deals 840 listings

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Used Toyota Highlander By Model Year

Year Average Price Deals Listings
2022 Toyota Highlander in Chicago
$49,523 Save $697 on - 18 listings
2021 Toyota Highlander in Chicago
$45,102 Save $3,335 on 3 deals 26 listings
2020 Toyota Highlander in Chicago
$41,866 Save $2,240 on 3 deals 23 listings
2019 Toyota Highlander in Chicago
$37,800 Save $4,947 on 8 deals 55 listings
2018 Toyota Highlander in Chicago
$34,813 Save $4,905 on 6 deals 25 listings
2017 Toyota Highlander in Chicago
$31,398 Save $5,591 on 9 deals 22 listings
2016 Toyota Highlander in Chicago
$28,524 Save $2,372 on 4 deals 17 listings

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Average Price Deals Listings
Toyota 4runner for Sale $36,706 Save $13,731 on 3,346 deals 11,129 listings
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Toyota Corolla for Sale $19,120 Save $6,166 on 2,902 deals 15,615 listings
Toyota Tacoma for Sale $34,304 Save $12,358 on 3,832 deals 16,917 listings
Toyota Tundra for Sale $36,962 Save $15,792 on 3,879 deals 12,375 listings

Average Price of Used Toyota Highlander for Sale in Chicago, IL Trims

Trim Average Price Listings Specs
Used Toyota Highlander for Sale in Chicago, IL XLE
(2014-2020)
$36,303 4,070 Listings
Body Style SUV
Drive Train AWD, FWD
Fuel Type Gasoline
Features see features...
Used Toyota Highlander for Sale in Chicago, IL Limited
(2002-2020)
$28,850 2,340 Listings
Body Style SUV
Drive Train AWD, FWD
Fuel Type Gasoline
Features see features...
Used Toyota Highlander for Sale in Chicago, IL LE
(2014-2020)
$31,961 1,600 Listings
Body Style SUV
Drive Train AWD, FWD
Fuel Type Gasoline
Features see features...
Used Toyota Highlander for Sale in Chicago, IL SE
(2010-2013, 2017-2019)
$29,045 917 Listings
Body Style SUV
Drive Train AWD, FWD
Fuel Type Gasoline
Features see features...
Used Toyota Highlander for Sale in Chicago, IL Base
(2001-2013)
$11,558 609 Listings
Body Style SUV
Drive Train AWD, FWD
Fuel Type Gasoline
Features see features...
Used Toyota Highlander for Sale in Chicago, IL LE Plus
(2014-2019)
$29,669 387 Listings
Body Style SUV
Drive Train AWD, FWD
Fuel Type Gasoline
Features see features...
Used Toyota Highlander for Sale in Chicago, IL Limited Platinum
(2014-2020)
$35,601 313 Listings
Body Style SUV
Drive Train AWD, FWD
Fuel Type Gasoline
Features see features...
Used Toyota Highlander for Sale in Chicago, IL Platinum
(2020)
$51,041 215 Listings
Body Style SUV
Drive Train AWD, FWD
Fuel Type Gasoline
Features see features...
Used Toyota Highlander for Sale in Chicago, IL XSE
(2021)
$49,526 184 Listings
Body Style SUV
Drive Train AWD, FWD
Fuel Type Gasoline
Used Toyota Highlander for Sale in Chicago, IL Sport
(2006-2010)
$11,553 164 Listings
Body Style SUV
Drive Train AWD, FWD
Fuel Type Gasoline
Features see features...
Explore Other Cities
  • Toyota Highlander in Billings Save $2,941 on 3 Deals
    14 Listings from $4,999
  • Toyota Highlander in Columbus Save $2,765 on 14 Deals
    81 Listings from $6,995

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