Used 2019 Toyota Highlander Price in Chicago, IL
Estimated market value based on depreciation, mileage, and regional factors. Dealer retail is around $24,001.
The Truth: If you pay more than $24,001 for this used Toyota Highlander, you're overpaying. A private party sale would cost around $21,556 — and the out-the-door cost at a dealer is approximately $25,822.
Used Car Value Breakdown
Depreciation & Value
Mileage
Vehicles with above-average mileage should be priced lower; below-average mileage commands a premium.
Price Breakdown
What's a Good Deal?
Estimated Out-the-Door Price
Includes average sale price + documentation fee ($321) + destination ($0) + estimated sales tax ($1,500)
Best time to buy: January typically sees the lowest prices.
Typical Fees to Watch
- Documentation fee: $321
- Destination charge: $0
- Estimated sales tax: $1,500
Local Market Factors
- Cost of living adjustment: +8% above national average
- Dealer competition: High (more negotiation room)
- Sales tax rate: 6.3%
Vehicle Overview
- Body type: SUV
- Vehicle age: 7 years old
- Estimated mileage: 94,500 miles (based on suv average)
- Original MSRP when new: $45,135
- Total depreciation: 53% since new
- Value retention: average — Average — typical depreciation for this segment
- Market demand: high — Above average — expect fewer discounts
When to Buy
Current month (May) is rated above-average for buying.
Best months to buy: January, September, October, November, December
Negotiation Tips
- Get a pre-purchase inspection before buying any used car in Chicago — it costs $100–200 and can save you thousands.
- Always check the vehicle history report (Carfax or AutoCheck) for accidents, title issues, and service records.
- The trade-in value for this vehicle is approximately $19,556. Use this as your floor when negotiating.
- The private party price is around $21,556 — buying from a private seller typically saves 10–15% vs a dealer.
- Check for open recalls at nhtsa.gov — dealers must fix recalls for free regardless of where you bought the car.
- This model depreciates faster than average — you may find better deals, but consider the ongoing depreciation in your total cost of ownership.
- Budget approximately $1,500 for sales tax on top of the purchase price.
Frequently Asked Questions
What is a 2019 Toyota Highlander worth in Chicago?
Based on current market estimates, the dealer retail price for a 2019 Toyota Highlander in Chicago is approximately $24,001. The private party value is around $21,556, and the trade-in value is approximately $19,556.
How much has the 2019 Toyota Highlander depreciated?
The 2019 Toyota Highlander has depreciated approximately 53% from its original MSRP of $45,135. That’s a total loss of approximately $23,922. It will lose roughly $1,805 more over the next year.
What is the trade-in value for a 2019 Toyota Highlander?
The estimated trade-in value in Chicago is approximately $19,556. This is what a dealer would typically offer. You can usually get more selling private party (estimated $21,556).
Is a 2019 Toyota Highlander a good deal right now?
A good deal on a 2019 Toyota Highlander in Chicago is anything below $22,561. If you’re paying above $25,441, you’re likely overpaying. Check whether the vehicle has average mileage for its age — above-average mileage should bring the price down.
Should I buy from a dealer or private party?
Private party purchases typically save you $2,445 compared to a dealer in Chicago. However, dealers often include limited warranties and handle paperwork. Weigh the savings against the convenience and any included protection.