Page № 5 - Used Toyota Highlander for Sale in Chicago, IL

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$37,250
$37,250 above
$1,098/mo est. ?
116,270 km 2.5L

Toyota of Naperville

4.8 Google 5181 reviews

60540, Naperville IL

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$21,495
$21,495 above
$634/mo est. ?
112,306 km

Valley Honda

4.8 Google 3155 reviews

60504, Aurora IL

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206,387 km 3.5L

Toyota of Naperville

4.8 Google 5181 reviews

60540, Naperville IL

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$8,500
$8,500 above
$251/mo est. ?
338,750 km

Toyota of Naperville

4.8 Google 5181 reviews

60540, Naperville IL

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$24,995
$24,995 above
$737/mo est. ?
136,488 km 3.5L

Smart Buy Auto Finance

4.7 Google 362 reviews

46319, Griffith IN

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$28,840
$28,840 above
$850/mo est. ?
99,243 km

Main Street Motors

46368, Portage IN

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$8,000
$8,000 above
$236/mo est. ?
231,145 km

Gmotorcars, Inc.

4.3 Google 138 reviews

60005, Arlington Heights IL

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$54,323
$54,323 above
$1,599/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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$43,998
$43,998 above
$1,297/mo est. ?
27,187 km

CarMax Schaumburg

4.5
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6 reviews

60173, Schaumburg IL

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$35,990
$35,990 above
$1,061/mo est. ?
130,635 km 2.5L

Bettenhausen Chrysler Dodge Jeep RAM

4.6 Google 2318 reviews

60477, Tinley Park IL

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$33,300
$33,300 above
$982/mo est. ?
22,840 km

Team Toyota

46375, Schererville IN

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$17,485
$17,485 above
$516/mo est. ?
189,558 km

Rod Baker Ford Sls

4.3 Google 649 reviews

60544, Plainfield IL

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$30,190
$30,190 above
$890/mo est. ?
87,275 km

Elgin Toyota

60107, Streamwood IL

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$22,495
$22,495 above
$663/mo est. ?
165,323 km

Car City Inc

4.5 Google 355 reviews

60074, Palatine IL

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$55,521
$55,521 above
$1,637/mo est. ?
18,955 km 2.5L

Toyota of Naperville

4.8 Google 5181 reviews

60540, Naperville IL

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$57,758
$57,758 above
$1,700/mo est. ?
0 km

BredemannToyotaScion Fleet

60068, Park Ridge IL

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$42,595
$42,595 above
$1,256/mo est. ?
22,542 km

Arlington Acura in Palatine

4.5 Google 1629 reviews

60074, Palatine IL

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$12,500
$12,500 above
$369/mo est. ?
177,684 km

Napleton's Palatine Mazda

60074, Palatine IL

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$51,522
$51,522 above
$1,516/mo est. ?
5 km

Gerald Toyota of Matteson

4.5 Google 944 reviews

60443, Matteson IL

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$31,995
$31,995 above
$943/mo est. ?
142,520 km

Highend Motors 2

46410, Merrillville IN

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$41,998
$41,998 above
$1,238/mo est. ?
62,510 km

CarMax Tinley Park

1.0
Star icon
1 review

60477, Tinley Park IL

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$55,498
$55,498 above
$1,633/mo est. ?
0 km

Toyota of Naperville

4.8 Google 5181 reviews

60540, Naperville IL

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$58,198
$58,198 above
$1,713/mo est. ?
0 km

Toyota of Naperville

4.8 Google 5181 reviews

60540, Naperville 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.