Chicago, IL · 50-mile radius
Used Toyota Highlander deals near Chicago, IL
The median asking price is $26,999 across 417 used vehicles within 50 miles of Chicago, IL. 80 are priced 5–30% below OttoQuest’s estimate for a comparable car.
Inventory checked over 7 days ending · Latest sighting
- Median asking price
- $26,999
- Middle half of asking prices
- $17,495 – $35,690
- First seen in the past 7 days
- 125
Best deals near Chicago, IL
Ranked by how far each asking price is below its own estimated value.
- $7,999▼ 30% belowEst. $11,381
- $4,450▼ 29% belowEst. $6,304
- $4,900▼ 27% belowEst. $6,710
- $6,500▼ 26% belowEst. $8,779
- $29,900▼ 22% belowEst. $38,479
- $11,754▼ 18% belowEst. $14,250
Recently spotted near Chicago, IL
Matching cars we first saw in the past 7 days, newest sightings first.
- $7,875
- $15,368
- $21,400
- $21,407
- $4,750
Asking prices by model year
The most listed model years in this search. Mileage helps explain some of the difference in asking prices.
| Year | Cars | Median ask | Median miles |
|---|---|---|---|
| 2024 | 33 | $39,905 | 33,080 |
| 2023 | 46 | $33,922 | 57,023 |
| 2022 | 33 | $31,582 | 73,219 |
| 2021 | 35 | $29,998 | 78,069 |
| 2019 | 32 | $26,422 | 82,000 |
| 2018 | 28 | $23,494 | 93,137 |
More local markets
Other used cars near Chicago, IL
Used Toyota Highlander in other cities
How these numbers are calculated
What do the prices represent?
These are advertised asking prices for used and certified pre-owned vehicles, before taxes and registration. We use the lowest qualifying asking price per vehicle within 50 straight-line miles of the city center. The middle half is the range from the 25th to the 75th percentile. The median is a benchmark for this search; trim, mileage and condition affect what an individual car is worth.
What qualifies as a deal?
The price has to be 5–30% below our estimate, based on at least eight comparables for the same trim and model year. The estimate accounts for mileage where available, reported history and state. We leave out known modified cars from the deal ranking and exclude reported title issues from this search. Missing history doesn’t mean a car is clean. Confirm availability, vehicle history and the out-the-door price before visiting.