Page № 3 - Used Toyota Highlander for Sale in Chicago, IL

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$17,500
$17,500 above
$516/mo est. ?
210,912 km 3.5L

60482, Worth IL

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$11,988
$11,988 above
$354/mo est. ?
160,052 km

Gerald Toyota of Matteson

4.5 Google 944 reviews

60443, Matteson IL

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$21,299
$21,299 above
$628/mo est. ?
154,611 km

60642, Chicago IL

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$27,395
$27,395 above
$808/mo est. ?
129,335 km

McGrath Acura in Morton Grove

4.1 Google 833 reviews

60053, Morton Grove IL

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$24,000
$24,000 above
$708/mo est. ?
164,235 km

Zeigler Chevrolet

4.5 Google 4243 reviews

60173, Schaumburg IL

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$31,745
$31,745 above
$936/mo est. ?
76,889 km

Jidd Motors Mitsubishi

60016, Des Plaines IL

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$18,500
$18,500 above
$546/mo est. ?
180,494 km 3.5L

KD Motorsport

4.8 Google 150 reviews

60074, Palatine IL

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$38,288
$38,288 above
$1,129/mo est. ?
76,585 km

Toyota of Naperville

4.8 Google 5181 reviews

60540, Naperville IL

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$8,990
$8,990 above
$265/mo est. ?
235,770 km

NB Motors

60540, Naperville IL

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$6,998
$6,998 above
$206/mo est. ?
227,308 km 3.3L

60564, Naperville IL

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$32,988
$32,988 above
$973/mo est. ?
140,856 km

McGrath Lexus Chicago

4.5 Google 1101 reviews

60622, Chicago IL

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$30,895
$30,895 above
$911/mo est. ?
118,116 km

Fair Oaks Ford Lincoln

4.6 Google 2114 reviews

60540, Naperville IL

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$42,998
$42,998 above
$1,268/mo est. ?
45,076 km 2.5L

CarMax Hillside (Eisenhower Expy) - Offering Express Pickup

60162, Hillside IL

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$36,998
$36,998 above
$1,091/mo est. ?
98,728 km

CarMax Schaumburg

4.5
Star icon
6 reviews

60173, Schaumburg IL

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$24,400
$24,400 above
$720/mo est. ?
107,282 km

Team Toyota

46375, Schererville IN

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$31,998
$31,998 above
$944/mo est. ?
49,576 km

CarMax Hillside (Eisenhower Expy) - Offering Express Pickup

60162, Hillside IL

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$43,990
$43,990 above
$1,297/mo est. ?
34,631 km

Elgin Toyota

60107, Streamwood IL

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$25,995
$25,995 above
$767/mo est. ?
75,132 km 3.5L

Wida Motor Group

5.0 Google 31 reviews

60440, Bolingbrook IL

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$40,990
$40,990 above
$1,209/mo est. ?
31,241 km 2.5L

Chicago Northside Toyota

60659, Chicago IL

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$28,694
$28,694 above
$846/mo est. ?
124,453 km

Silver Auto Sales and Service

4.3 Google 213 reviews

60423, Frankfort IL

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$51,900
$51,900 above
$1,530/mo est. ?
18,969 km

Toyota of Naperville

4.8 Google 5181 reviews

60540, Naperville IL

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$29,490
$29,490 above
$870/mo est. ?
122,365 km 2.5L

Elgin Toyota

60107, Streamwood IL

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$32,790
$32,790 above
$967/mo est. ?
127,658 km 2.5L

Elgin Toyota

60107, Streamwood IL

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$32,000
$32,000 above
$944/mo est. ?
108,498 km 2.5L

Nelson Automotive

4.6 Google 134 reviews

60056, Mount Prospect 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.