Page № 6 - Used Toyota Highlander for Sale in Chicago, IL

Showing 24 of 371 listings

No matches found.

Save your search and we will notify you when we have cars that match your search criteria.

We expanded your search distance and we're unable to find cars that match.

Try adjusting your filters, or start a new search.

$41,999
$41,999 above
$1,238/mo est. ?
69,400 km

Orland Toyota

60487, Tinley Park IL

Check Details
$26,444
$26,444 above
$780/mo est. ?
187,094 km

McGrath Elmhurst Toyota

60126, Elmhurst IL

Check Details
$37,888
$37,888 above
$1,117/mo est. ?
75,171 km 2.5L

60532, Lisle IL

Check Details
$40,997
$40,997 above
$1,209/mo est. ?
27,138 km

60074, Palatine IL

Check Details
$22,900
$22,900 above
$675/mo est. ?
126 km

Land Rover of Naperville

60540, Naperville IL

Check Details
$21,000
$21,000 above
$619/mo est. ?
185,637 km

Team Toyota

46375, Schererville IN

Check Details
$21,143
$21,143 above
$623/mo est. ?
190,903 km

Audi Westmont

60559, Westmont IL

Check Details
$33,998
$33,998 above
$1,003/mo est. ?
95,968 km

CarMax Oak Lawn

5.0
Star icon
2 reviews

60453, Oak Lawn IL

Check Details
$37,998
$37,998 above
$1,121/mo est. ?
105,119 km

CarMax Naperville

3.4
Star icon
2 reviews

60563, Naperville IL

Check Details
$43,998
$43,998 above
$1,297/mo est. ?
40,349 km

CarMax Naperville

3.4
Star icon
2 reviews

60563, Naperville IL

Check Details
$32,996
$32,996 above
$973/mo est. ?
38,912 km

60074, Palatine IL

Check Details
$47,684
$47,684 above
$1,406/mo est. ?
71,154 km

60074, Palatine IL

Check Details
$14,999
$14,999 above
$442/mo est. ?
181,221 km

FAIR OAKS LINCOLN

60540, Naperville IL

Check Details
$35,490
$35,490 above
$1,047/mo est. ?
98,772 km

Chicago Northside Toyota

60659, Chicago IL

Check Details
$55,288
$55,288 above
$1,627/mo est. ?
0 km

Bredemann Toyota

4.6 Google 2103 reviews

60068, Park Ridge IL

Check Details
$49,128
$49,128 above
$1,446/mo est. ?
0 km

Bredemann Toyota

4.6 Google 2103 reviews

60068, Park Ridge IL

Check Details
$48,828
$48,828 above
$1,437/mo est. ?
0 km

Chicago Northside Toyota

60659, Chicago IL

Check Details
$16,789
$16,789 above
$495/mo est. ?
221,289 km

60564, Naperville IL

Check Details
$40,456
$40,456 above
$1,193/mo est. ?
72,811 km

Schaumburg Toyota

4.4 Google 2723 reviews

60194, Schaumburg IL

Check Details
$31,801
$31,801 above
$938/mo est. ?
125,303 km

Elgin Hyundai

60103, Bartlett IL

Check Details
$32,980
$32,980 above
$973/mo est. ?
100,993 km

Driven Auto Sales

4.7 Google 679 reviews

60459, Burbank IL

Check Details
$37,998
$37,998 above
$1,121/mo est. ?
37,118 km

CarMax Schaumburg

4.5
Star icon
6 reviews

60173, Schaumburg IL

Check Details
$20,995
$20,995 above
$619/mo est. ?
152,874 km

Affinity Auto Sales

60185, West Chicago IL

Check Details
$39,998
$39,998 above
$1,179/mo est. ?
63,130 km

CarMax Merrillville

4.7
Star icon
2 reviews

46410, Merrillville IN

Check Details

Frequently Asked Questions

Our marketplace currently lists 371 used cars in Chicago, IL from dealers and private sellers. Prices range from $12,927 to $57,963.

Top brands by active listings in Chicago, IL are Toyota. The mix often reflects local buying preferences.

The average listed price in Chicago, IL is $33,393. Browse by budget: under $10,000, under $20,000, or under $30,000.

No — you can buy from a seller in Chicago, IL regardless of your state of residence. You'll need to register and title the vehicle in your home state within the required window (usually 30 days). Local dealers typically handle paperwork for out-of-state buyers.

Yes — popular nearby options include cities across the state. You can also browse all used cars in Illinois.