Used Toyota Highlander for Sale in Chicago, IL

1-20 of 338 Cars Found
Save Search
View on dealer site
2006 Toyota Highlander Base

2006 Toyota Highlander Base - 162,810 mi

Midlothian, IL (15 mi) - Listed 21 days ago
  • $1,810 below market price
  • dealer rating
  • 1 price drop in 22 days
$6,999
PREVIEW
2011 Toyota Highlander SE

2011 Toyota Highlander SE - 57,093 mi

Schaumburg, IL (27 mi) - Listed 32 days ago
  • $3,063 below market price
  • dealer rating
  • 1-owner, low annual miles
$16,444
PREVIEW
iSeeCars Unbiased Insights

How can you save money on a used Toyota Highlander?

  • Highlander

    $37,962
    $6,587 Savings

    Highlander Hybrid

    $44,548
  • 4-Cylinder

    $28,327
    $4,636 Savings

    6-Cylinder

    $32,963
  • FWD

    $36,260
    $2,211 Savings

    AWD

    $38,472

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

Gold

$1,850Average Savings

Most
Expensive

Blue

$955Average Premium

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

View on dealer site
2002 Toyota Highlander Base

2002 Toyota Highlander Base - 174,547 mi

Elgin, IL (33 mi) - Listed 7 days ago
  • $734 below market price
  • dealer rating
PREVIEW
2013 Toyota Highlander Limited

2013 Toyota Highlander Limited - 121,813 mi

Naperville, IL (25 mi) - Listed 82 days ago
  • $3,027 below market price
  • dealer rating
  • 1-owner
$14,993
PREVIEW
2003 Toyota Highlander Base

2003 Toyota Highlander Base - 139,888 mi

Palatine, IL (27 mi) - Listed 10 days ago
  • $906 below market price
  • dealer rating
  • 1-owner
PREVIEW
View on dealer site
2004 Toyota Highlander Sport Utility 4D

2004 Toyota Highlander Sport Utili - 221,170 mi

Franklin Park, IL (12 mi) - Listed 181 days ago
  • $1,076 below market price
  • dealer rating
  • 1 price drop in 182 days
$3,700
PREVIEW
2007 Toyota Highlander Base

2007 Toyota Highlander Base - 134,411 mi

Palatine, IL (27 mi) - Listed 24 days ago
  • $1,326 below market price
  • dealer rating
  • 1 price drop in 25 days
$6,913
PREVIEW
View on dealer site
2013 Toyota Highlander Sport Utility 4D

2013 Toyota Highlander Sport Utili - 177,140 mi

Posen, IL (15 mi) - Listed 41 days ago
  • $2,131 below market price
  • dealer rating
  • 1 price drop in 42 days
$10,999
PREVIEW
2015 Toyota Highlander LE

2015 Toyota Highlander LE - 109,536 mi

Summit Argo, IL (9 mi) - Listed 28 days ago
  • $2,004 below market price
  • dealer rating
PREVIEW
2015 Toyota Highlander Limited Platinum

2015 Toyota Highlander Limited Pla - 165,713 mi

North Aurora, IL (37 mi) - Listed 4 days ago
  • $2,268 below market price
  • dealer rating
PREVIEW
View on dealer site
2011 Toyota Highlander Sport Utility 4D

2011 Toyota Highlander Sport Utili - 173,918 mi

Michigan City, IN (40 mi) - Listed 109 days ago
  • $1,654 below market price
  • dealer rating
  • 2 price drops in 110 days
$9,495
PREVIEW
View on dealer site
2009 Toyota Highlander Limited

2009 Toyota Highlander Limited - 173,825 mi

Willowbrook, IL (15 mi) - Listed 91 days ago
  • $1,297 below market price
  • dealer rating
  • 3 price drops in 92 days
$9,490
PREVIEW
2009 Toyota Highlander Sport

2009 Toyota Highlander Sport - 257,120 mi

Highland Park, IL (23 mi) - Listed 32 days ago
  • $700 below market price
  • dealer rating
  • 1 price drop in 33 days
$5,881
PREVIEW
View on dealer site
2002 Toyota Highlander Sport Utility 4D

2002 Toyota Highlander Sport Utili - 125,000 mi

Melrose Park, IL (13 mi) - Listed 219 days ago
  • $947 below market price
PREVIEW
2012 Toyota Highlander Limited

2012 Toyota Highlander Limited - 114,526 mi

Addison, IL (19 mi) - Listed 26 days ago
  • $1,218 below market price
  • dealer rating
  • 1-owner
$15,950
PREVIEW
2023 Toyota Highlander L

2023 Toyota Highlander L - 1,774 mi

Libertyville, IL (34 mi) - Listed 118 days ago
  • $4,100 below market price
  • dealer rating
  • 1-owner, low annual miles
$38,910
PREVIEW
2020 Toyota Highlander XLE

2020 Toyota Highlander XLE - 15,876 mi

Northbrook, IL (21 mi) - Listed 1 day ago
  • $1,327 below market price
  • dealer rating
  • low annual miles
PREVIEW
2020 Toyota Highlander LE

2020 Toyota Highlander LE - 19,550 mi

Fox Lake, IL (46 mi) - Listed 11 days ago
  • $878 below market price
  • dealer rating
  • 1-owner, low annual miles
PREVIEW
2018 Toyota Highlander XLE

2018 Toyota Highlander XLE - 35,526 mi

Barrington, IL (33 mi) - Listed 54 days ago
  • $2,268 below market price
  • dealer rating
  • 1-owner, low annual miles
PREVIEW
2021 Toyota Highlander XLE

2021 Toyota Highlander XLE - 39,896 mi

Saint Charles, IL (32 mi) - Listed 9 days ago
  • $869 below market price
  • dealer rating
  • 1-owner, low annual miles
$33,500
PREVIEW
X
Would you like to view the latest search results ?
Yes     No
Zip Code Required X

Please enter a five-digit zip code to find cars for sale near you.

Used Toyota Highlander Pricing in Chicago

Average Price
$30,409
For a used Toyota Highlander
Average Savings
$1,432
Based on all Highlander deals found
Biggest Savings
$4,100
Below estimated market price
Good Deal
$26,906
Typical price of a good deal

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

Fuel Type A Highlander averages $6,587 less than a Highlander Hybrid
Engine A 4-Cylinder Highlander costs $4,636 less than a 6-Cylinder
Drive Type A front-wheel drive (FWD) Toyota Highlander can be priced $2,211 less than an all-wheel drive (AWD)

Buying Tips

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

Rank Color Compared to Avg Price
1 Gold $1,850 Savings
2 Brown $742 Savings
3 Orange $675 Savings
4 Silver $603 Savings
5 Black $200 Savings
6 White $18 Savings
7 Red $63 Higher
8 Green $191 Higher
9 Gray $329 Higher
10 Blue $955 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?

  • 338 cars for sale found, starting at $3,300
  • Average price for Used Toyota Highlander Chicago, IL: $30,409
  • 91 deals found. Average savings of $1,432
  • Save up to $4,100 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
Gold $1,850Average Savings
Most Expensive Color
Blue $955Average Premium
Total saved by iSeeCars users

$414,738,423

Start searching smarter now

Similar Models

Average Price Deals Listings
BMW X1 for Sale $27,051 Save $7,736 on 750 deals 2,030 listings
Chevrolet Traverse for Sale $25,947 Save $9,985 on 2,432 deals 7,463 listings
Dodge Durango for Sale $37,808 Save $14,844 on 1,661 deals 6,646 listings
Ford Explorer for Sale $33,713 Save $11,429 on 6,900 deals 26,382 listings
Honda Pilot for Sale $30,670 Save $10,217 on 2,551 deals 10,077 listings
Hyundai Santa Fe for Sale $33,173 Save $7,563 on 2,293 deals 13,040 listings
Jeep Grand Cherokee for Sale $32,301 Save $18,252 on 6,755 deals 20,731 listings
Mazda CX-9 for Sale $25,229 Save $6,546 on 733 deals 1,994 listings
Nissan Murano for Sale $27,414 Save $6,840 on 1,833 deals 6,124 listings
Nissan Pathfinder for Sale $32,572 Save $6,963 on 1,492 deals 6,874 listings

Popular Toyota Models

Average Price Deals Listings
Toyota 4runner for Sale $36,095 Save $7,547 on 1,430 deals 8,171 listings
Toyota Camry for Sale $21,978 Save $6,157 on 3,719 deals 18,005 listings
Toyota Corolla for Sale $18,135 Save $6,058 on 3,196 deals 12,494 listings
Toyota Tacoma for Sale $34,143 Save $9,369 on 2,100 deals 13,880 listings
Toyota Tundra for Sale $46,516 Save $13,220 on 1,615 deals 9,892 listings

Explore other cities

Average Price Deals Listings
Toyota Highlander in Milwaukee $30,308 Save $3,630 on 42 deals 116 listings
Toyota Highlander in Holland $33,071 Save $3,889 on 18 deals 86 listings
Toyota Highlander in Madison $30,040 Save $2,646 on 9 deals 45 listings
Toyota Highlander in Grand Rapids $33,081 Save $3,889 on 17 deals 85 listings
Toyota Highlander in Green Bay $32,901 Save $2,590 on 7 deals 36 listings
Toyota Highlander in Springfield $33,354 Save $3,136 on 5 deals 34 listings
Toyota Highlander in Iowa City $32,946 Save $3,966 on 20 deals 79 listings
Toyota Highlander in Evansville $33,112 Save $3,799 on 10 deals 50 listings
Toyota Highlander in Cedar Rapids $30,741 Save $3,760 on 26 deals 83 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)
$30,849 3,209 Listings
Body Style SUV
Drive Train AWD, FWD
Fuel Type Gas
Features see features...
Used Toyota Highlander for Sale in Chicago, IL Limited
(2002-2020)
$24,187 1,641 Listings
Body Style SUV
Drive Train AWD, FWD
Fuel Type Gas
Features see features...
Used Toyota Highlander for Sale in Chicago, IL LE
(2014-2020)
$27,976 1,116 Listings
Body Style SUV
Drive Train AWD, FWD
Fuel Type Gas
Features see features...
Used Toyota Highlander for Sale in Chicago, IL SE
(2010-2013, 2017-2019)
$19,896 509 Listings
Body Style SUV
Drive Train AWD, FWD
Fuel Type Gas
Features see features...
Used Toyota Highlander for Sale in Chicago, IL Base
(2001-2013)
$9,677 475 Listings
Body Style SUV
Drive Train AWD, FWD
Fuel Type Gas
Features see features...
Used Toyota Highlander for Sale in Chicago, IL XSE
(2021)
$38,910 430 Listings
Body Style SUV
Drive Train AWD, FWD
Fuel Type Gas
Used Toyota Highlander for Sale in Chicago, IL L
(2020)
$33,155 371 Listings
Body Style SUV
Drive Train AWD, FWD
Fuel Type Gas
Features see features...
Used Toyota Highlander for Sale in Chicago, IL Platinum
(2020)
$41,791 349 Listings
Body Style SUV
Drive Train AWD, FWD
Fuel Type Gas
Features see features...
Used Toyota Highlander for Sale in Chicago, IL LE Plus
(2014-2019)
$22,054 178 Listings
Body Style SUV
Drive Train AWD, FWD
Fuel Type Gas
Features see features...
Used Toyota Highlander for Sale in Chicago, IL Limited Platinum
(2014-2020)
$26,786 176 Listings
Body Style SUV
Drive Train AWD, FWD
Fuel Type Gas
Features see features...
Keep me posted on new listings X
Do you have a price in mind?
Let us know and we can send you better matches.
By clicking "Subscribe" you agree to our Terms and Privacy Policy.
Save This Car X
GET ALERTS
By clicking "Start Tracking" you agree to our Terms and Privacy Policy.
Save This Search X
Be the first to see new listings
and price drops for your search.
GET ALERTS
By clicking "Get Alerts" you agree to our Terms and Privacy Policy.