Page № 9 - 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.

$24,998
$24,998 above
$737/mo est. ?
164,953 km

CarMax Joliet

60586, Plainfield IL

Check Details
$39,998
$39,998 above
$1,179/mo est. ?
69,073 km

CarMax Oak Lawn

5.0
Star icon
2 reviews

60453, Oak Lawn IL

Check Details
$34,795
$34,795 above
$1,026/mo est. ?
53,036 km

Toyota on Western

5.0
Star icon
5 reviews
4.1 Google 794 reviews

60636, Chicago IL

Check Details
$37,995
$37,995 above
$1,120/mo est. ?
104,142 km 2.5L

The Autobarn Volvo of Oak Park

4.6 Google 533 reviews

60304, Oak Park IL

Check Details
$21,290
$21,290 above
$628/mo est. ?
120,248 km

Elgin Hyundai

60103, Bartlett IL

Check Details
$32,598
$32,598 above
$961/mo est. ?
101,004 km

Toyota of Naperville

4.8 Google 5181 reviews

60540, Naperville IL

Check Details
$48,599
$48,599 above
$1,433/mo est. ?
53,570 km 2.5L

60642, Chicago IL

Check Details
$38,990
$38,990 above
$1,150/mo est. ?
50,913 km

Elgin Toyota

60107, Streamwood IL

Check Details
$23,456
$23,456 above
$692/mo est. ?
135,967 km

Schaumburg Toyota

4.4 Google 2723 reviews

60194, Schaumburg IL

Check Details
$25,999
$25,999 above
$767/mo est. ?
92,265 km

Arlington Toyota

60074, Palatine IL

Check Details
$29,500
$29,500 above
$870/mo est. ?
123,129 km 2.5L

Ed Napleton Honda in River Oaks

60438, Lansing IL

Check Details
$19,995
$19,995 above
$590/mo est. ?
180,708 km 3.5L

High Quality Auto Group

60632, Chicago IL

Check Details
$42,990
$42,990 above
$1,268/mo est. ?
51,393 km

Elgin Toyota

60107, Streamwood IL

Check Details
$8,989
$8,989 above
$265/mo est. ?
241,932 km

Family Hyundai

60477, Tinley Park IL

Check Details
$43,599
$43,599 above
$1,286/mo est. ?
50,091 km

60642, Chicago IL

Check Details
$36,990
$36,990 above
$1,091/mo est. ?
112,528 km

Elgin Toyota

60107, Streamwood IL

Check Details
$30,495
$30,495 above
$899/mo est. ?
108,696 km

INFINITI of Naperville

4.6 Google 972 reviews

60540, Naperville IL

Check Details
$24,900
$24,900 above
$734/mo est. ?
169,956 km

Zeigler Subaru of Merrillville

46375, Schererville IN

Check Details
$25,000
$25,000 above
$737/mo est. ?
147,417 km

Team Toyota

46375, Schererville IN

Check Details
$27,988
$27,988 above
$825/mo est. ?
87,955 km

McGrath Lexus of Westmont

60559, Westmont IL

Check Details
$34,990
$34,990 above
$1,032/mo est. ?
65,920 km

Elgin Toyota

60107, Streamwood IL

Check Details
$35,100
$35,100 above
$1,035/mo est. ?
95,048 km 2.5L

Team Toyota

46375, Schererville IN

Check Details
$58,506
$58,506 above
$1,722/mo est. ?
0 km 2.5L

Oakbrook Toyota in Westmont

4.6 Google 3096 reviews

60559, Westmont IL

Check Details
$58,506
$58,506 above
$1,722/mo est. ?
0 km 2.5L

Oakbrook Toyota in Westmont

4.6 Google 3096 reviews

60559, Westmont IL

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.