Page № 8 - Used Toyota Highlander for Sale in Chicago, IL

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$57,731
$57,731 above
$1,699/mo est. ?
0 km 2.5L

Oakbrook Toyota in Westmont

4.6 Google 3096 reviews

60559, Westmont IL

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$58,106
$58,106 above
$1,710/mo est. ?
0 km 2.5L

Oakbrook Toyota in Westmont

4.6 Google 3096 reviews

60559, Westmont IL

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$38,990
$38,990 above
$1,150/mo est. ?
56,966 km

Chicago Northside Toyota

60659, Chicago IL

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$19,997
$19,997 above
$590/mo est. ?
150,047 km

Access Automotive LLC

60106, Bensenville IL

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263,473 km

Transit Motors

4.7
Star icon
8 reviews
4.4 Google 107 reviews

60409, Calumet City IL

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$8,999
$8,999 above
$265/mo est. ?
248,357 km 3.3L

AUTOSAVIN

60181, Villa Park IL

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$26,106
$26,106 above
$770/mo est. ?
96,816 km

Napleton's Palatine Mazda

60074, Palatine IL

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$13,929
$13,929 above
$411/mo est. ?
218,923 km

Gregory Hyundai

4.3 Google 732 reviews

60035, Highland Park IL

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$11,310
$11,310 above
$334/mo est. ?
152,055 km

Oak Lawn Toyota

4.5 Google 1773 reviews

60453, Oak Lawn IL

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$38,157
$38,157 above
$1,125/mo est. ?
84,682 km 2.5L

Oak Lawn Toyota

4.5 Google 1773 reviews

60453, Oak Lawn IL

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$23,517
$23,517 above
$693/mo est. ?
138,938 km

Chevrolet of Naperville

4.6 Google 1385 reviews

60540, NAPERVILLE IL

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$22,141
$22,141 above
$653/mo est. ?
183,318 km

Napleton Mazda of Naperville

4.7 Google 1328 reviews

60540, Naperville IL

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$54,983
$54,983 above
$1,618/mo est. ?
0 km

Bredemann Toyota

4.6 Google 2103 reviews

60068, Park Ridge IL

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$32,500
$32,500 above
$958/mo est. ?
90,921 km

INFINITI of Naperville

4.6 Google 972 reviews

60540, Naperville IL

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$31,800
$31,800 above
$938/mo est. ?
51,711 km

Oakbrook Toyota in Westmont

4.6 Google 3096 reviews

60559, Westmont IL

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$28,750
$28,750 above
$848/mo est. ?
116,608 km

60642, Chicago IL

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$25,997
$25,997 above
$767/mo est. ?
61,564 km

Continental Toyota

4.3 Google 1810 reviews

60525, Hodgkins IL

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$28,927
$28,927 above
$853/mo est. ?
91,327 km

Toyota on Western

5.0
Star icon
5 reviews
4.1 Google 794 reviews

60636, Chicago IL

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$24,431
$24,431 above
$720/mo est. ?
152,461 km

Toyota of Naperville

4.8 Google 5181 reviews

60540, Naperville IL

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$17,995
$17,995 above
$531/mo est. ?
165,334 km 3.5L

60445, Crestwood IL

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$20,777
$20,777 above
$613/mo est. ?
158,782 km

McGrath Elmhurst Toyota

60126, Elmhurst IL

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$37,000
$37,000 above
$1,091/mo est. ?
95,221 km 2.5L

Nelson Automotive

4.6 Google 134 reviews

60056, Mount Prospect IL

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$31,900
$31,900 above
$941/mo est. ?
120,844 km

Bettenhausen Chrysler Dodge Jeep RAM

60441, Lockport IL

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$17,690
$17,690 above
$522/mo est. ?
208,406 km

Elgin Toyota

60107, Streamwood IL

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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.