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

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2003 Toyota Highlander Limited

2003 Toyota Highlander Limited - 201,304 mi

West Chicago, IL (29 mi) - Listed 58 days ago
  • $1,195 below market price
  • dealer rating
  • 1-owner , free CARFAX
PREVIEW
View on dealer site
2010 Toyota Highlander Base

2010 Toyota Highlander Base - 166,060 mi

Mokena, IL (25 mi) - Listed 24 days ago
  • $1,308 below market price
  • dealer rating
  • free CARFAX
$9,700
PREVIEW
iSeeCars Unbiased Insights

How can you save money on a used Toyota Highlander?

  • Highlander

    $30,076
    $6,477 Savings

    Highlander Hybrid

    $36,552
  • 4-Cylinder

    $24,452
    $5,015 Savings

    6-Cylinder

    $29,467
  • FWD

    $26,896
    $3,632 Savings

    AWD

    $30,527

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

Gray

$1,024Average Savings

Most
Expensive

Red

$883Average Premium

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

View on dealer site
2004 Toyota Highlander Sport Utility 4D

2004 Toyota Highlander Sport Utili - 180,955 mi

Chicago, IL (7 mi) - Listed 36 days ago
  • $1,068 below market price
  • dealer rating
  • 1 price drop in 37 days
$5,995
PREVIEW
View on dealer site
2011 Toyota Highlander Sport Utility 4D

2011 Toyota Highlander Sport Utili - 141,778 mi

Midlothian, IL (15 mi) - Listed 50 days ago
  • $1,580 below market price
  • dealer rating
PREVIEW
2005 Toyota Highlander Limited

2005 Toyota Highlander Limited - 134,533 mi

Michigan City, IN (40 mi) - Listed 51 days ago
  • $847 below market price
  • dealer rating
  • free CARFAX
PREVIEW
2015 Toyota Highlander Limited Platinum

2015 Toyota Highlander Limited Plat - 34,253 mi

Rolling Meadows, IL (24 mi) - Listed today
  • $1,933 below market price
  • dealer rating
  • low miles
PREVIEW
Home Delivery
2021 Toyota Highlander L

2021 Toyota Highlander L - 12,381 mi

- Listed 12 days ago
  • $4,022 below market price
  • low miles
PREVIEW
Home Delivery
2006 Toyota Highlander Limited

2006 Toyota Highlander Limited - 211,276 mi

Westmont, IL (17 mi) - Listed 8 days ago
  • $291 below market price
  • dealer rating
  • free CARFAX
$6,833
PREVIEW
Home Delivery
2020 Toyota Highlander L

2020 Toyota Highlander L - 29,475 mi

- Listed 13 days ago
  • $2,720 below market price
PREVIEW
2013 Toyota Highlander Highlander V6

2013 Toyota Highlander Highlander - 119,491 mi

Oak Forest, IL (17 mi) - Listed 58 days ago
  • $1,505 below market price
  • dealer rating
  • 3 price drops in 59 days
$17,900
PREVIEW
2017 Toyota Highlander SE

2017 Toyota Highlander SE - 79,945 mi

Kenosha, WI (49 mi) - Listed 78 days ago
  • $2,332 below market price
  • dealer rating
  • 4 price drops in 79 days
$28,976
PREVIEW
Home Delivery
2017 Toyota Highlander XLE

2017 Toyota Highlander XLE - 91,764 mi

- Listed 32 days ago
  • $1,925 below market price
  • 1 positive
  • 2 price drops in 33 days
$26,990
PREVIEW
2012 Toyota Highlander SE

2012 Toyota Highlander SE - 101,749 mi

Highland, IN (22 mi) - Listed 51 days ago
  • $440 below market price
  • dealer rating
  • free CARFAX
$16,300
PREVIEW
2010 Toyota Highlander Limited

2010 Toyota Highlander Limited - 111,799 mi

Addison, IL (19 mi) - Listed 1 day ago
  • $490 above market price
  • dealer rating
  • 1-owner , free CARFAX
PREVIEW
2016 Toyota Highlander XLE

2016 Toyota Highlander XLE - 97,713 mi

Chesterton, IN (35 mi) - Listed 5 days ago
  • $10 above market price
  • dealer rating
  • 1-owner , free CARFAX
PREVIEW
Home Delivery
2019 Toyota Highlander LE

2019 Toyota Highlander LE - 33,499 mi

Fox Lake, IL (46 mi) - Listed 39 days ago
  • $296 below market price
  • dealer rating
  • 1-owner , low miles , free CARFAX
$30,990
PREVIEW
Home Delivery
2019 Toyota Highlander LE

2019 Toyota Highlander LE - 13,477 mi

- Listed 1 day ago
  • $999 above market price
  • 1 positive , low miles
PREVIEW
Home Delivery
2014 Toyota Highlander XLE

2014 Toyota Highlander XLE - 56,755 mi

- Listed today
  • $669 above market price
  • low miles
PREVIEW
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Used Toyota Highlander Pricing in Chicago

Average Price
$32,095
For a used Toyota Highlander
Average Savings
$1,441
Based on all Highlander deals found
Biggest Savings
$4,022
Below estimated market price
Good Deal
$28,966
Typical price of a good deal

How to save money when buying a used Toyota Highlander in Chicago?

Fuel Type A Highlander averages $6,477 less than a Highlander Hybrid
Engine A 4-Cylinder Highlander costs $5,015 less than a 6-Cylinder
Drive Type A front-wheel drive (FWD) Toyota Highlander can be priced $3,632 less than an all-wheel drive (AWD)
Certified Choosing non-CPO vs Certified Pre-Owned (CPO) can save you $1,939 on a Toyota Highlander

Buying Tips

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

Rank Color Compared to Avg Price
1 Gray $1,024 Savings
2 Blue $619 Savings
3 Silver $577 Savings
4 Black $451 Savings
5 Brown $89 Higher
6 Beige $671 Higher
7 Green $673 Higher
8 White $760 Higher
9 Gold $822 Higher
10 Red $883 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

What is the average price for Used Toyota Highlander for Sale in Chicago, IL? How many are for sale and priced below market?

  • 425 cars for sale found, starting at $4,499
  • Average price for Used Toyota Highlander Chicago, IL: $32,095
  • 24 deals found. Average savings of $1,441
  • Save up to $4,022 below estimated market price
Search for a used Toyota Highlander in Chicago
See my listings

What colors are the best deals for a Toyota Highlander in Chicago?

Least Expensive Color
Gray $1,024Average Savings
Most Expensive Color
Red $883Average Premium
Total saved by iSeeCars users

$312,305,536

Start searching smarter now

Top Dealers Listing Used Toyota Highlander for Sale in Chicago, IL

Vroom - Get It Delivered Nationwide, Contact-Free
4.1 stars
58 Used Toyota Highlander for Sale in Chicago, IL for sale
Toyota of Naperville
Naperville, IL
3.1 stars
31 Used Toyota Highlander for Sale in Chicago, IL for sale
Elmhurst Toyota Scion
Elmhurst, IL
3.2 stars
12 Used Toyota Highlander for Sale in Chicago, IL for sale

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

Distance from Chicago, IL Average Price Deals Listings
50 miles
$32,254 Save $3,915 on 21 deals 301 listings
100 miles
$32,021 Save $3,915 on 30 deals 422 listings
200 miles
$31,670 Save $7,856 on 68 deals 798 listings

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Used Toyota Highlander By Model Year

Year Average Price Deals Listings
2022 Toyota Highlander in Chicago
$45,261 - 15 listings
2021 Toyota Highlander in Chicago
$47,770 Save $1,577 on 1 deal 41 listings
2020 Toyota Highlander in Chicago
$41,863 Save $3,915 on 1 deal 13 listings
2019 Toyota Highlander in Chicago
$37,090 Save $296 on - 54 listings
2018 Toyota Highlander in Chicago
$35,791 - 56 listings
2017 Toyota Highlander in Chicago
$31,629 Save $2,332 on 1 deal 25 listings
2016 Toyota Highlander in Chicago
$28,653 Save $3,449 on 1 deal 18 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)
$35,474 4,161 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)
$28,982 2,124 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)
$31,197 1,781 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)
$30,415 1,024 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)
$10,696 646 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)
$30,826 377 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)
$37,031 285 Listings
Body Style SUV
Drive Train AWD, FWD
Fuel Type Gasoline
Features see features...
Used Toyota Highlander for Sale in Chicago, IL Sport
(2006-2010)
$11,188 126 Listings
Body Style SUV
Drive Train AWD, FWD
Fuel Type Gasoline
Features see features...
Used Toyota Highlander for Sale in Chicago, IL Platinum
(2020)
$50,613 108 Listings
Body Style SUV
Drive Train AWD, FWD
Fuel Type Gasoline
Features see features...
Used Toyota Highlander for Sale in Chicago, IL XSE
(2021)
$47,599 75 Listings
Body Style SUV
Drive Train AWD, FWD
Fuel Type Gasoline
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