Used 2019 Toyota Highlander for Sale near Chicago, IL
186 results
CarGurus Analysis:
2019 Toyota Highlander
With 194 currently listed for sale near Chicago, IL and an average price of $24,781.00, 31.4% of 2019 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
Favorably reviewed: Owners rated the 2019 Toyota Highlander 4.76 / 5 stars.
87.6% of 2019 Highlander models on CarGurus are accident free.
CarGurus Analysis: 2019 Toyota Highlander
Summary
With 194 currently listed for sale near Chicago, IL and an average price of $24,781.00, 31.4% of 2019 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
Favorably reviewed: Owners rated the 2019 Toyota Highlander 4.76 / 5 stars.
87.6% of 2019 Highlander models on CarGurus are accident free.
Why it stands out
The 2019 Toyota Highlander continues to impress drivers with its spacious interior, comfort, and reliability, making it an appealing choice for families. Owners appreciate its safety features and reliable engine performance. While some users desire more rear seat space and find the pricing on the higher side, the Highlander offers a notably smooth ride and remains a top pick in the midsize SUV segment. It stands out for its combination of SUV utility with unibody design advantages, like fuel efficiency and handling that many competitors struggle to match. Overall, the 2019 Highlander's blend of comfort, safety, and versatile cargo space solidifies its reputation as a dependable family vehicle.
Other model years to consider
- Average price: $35,820.00
- Good/great deal percentage: 56.4%
- User rating: 5 / 5
- Total listings: 202
- Average price: $35,552.00
- Good/great deal percentage: 57.0%
- User rating: 4.75 / 5
- Total listings: 242
- Average price: $30,124.00
- Good/great deal percentage: 43.9%
- User rating: 4.86 / 5
- Total listings: 187
This analysis is based on CarGurus' proprietary market data from May 26, 2026, CarGurus experts' opinions, and generative AI.
Relevant articles
Toyota Highlander Buying Guide: Cost, Reliability, and the Best Years to Buy
Discover the ultimate buying guide for purchasing a used Toyota Highlander, covering every generation since 2001. Whether you're a first-time buyer or a Toyota loyalist, this comprehensive overview will help you research your next pre-owned Toyota Highlander.
The Best Three-Row SUVs of 2026
There’s no escaping it: SUVs are everywhere. Minivans offer the space for the most passengers and gear, but big, three-row SUVs deliver on both while offering some level of performance, on and off the paved roads.
The Best Used SUVs Under $10,000 in 2026
Can you get a great SUV for less than $10,000? Heck, yes! Our guide runs through the top 10, with options including family favorites and some upscale options.
4.8 Overall rating
Filter by rating
Simone P
Reviewed a 2019 Toyota SE FWD on Aug 10, 2025
I just purchased a pre-owner Toyota Highlander. I picked the 2019 model because it is the last model year that had the rear window that opened independently from the lift gate. I missed that feature in my last two Honda CRV’s because the older (gen 1 &2) Honda CRV’s used to have that feature too. Both the CRV and Highlander have similar features and are both reliable and wonderful cars, which will last a long time. I just needed a larger car for my current needs. The Honda did get better gas mileage than the Toyota, but it was also a smaller SUV. I have owned different Honda CR-Vs for the last 30 years, and have been very happy with them. This is my first Toyota. The Highlander is very comfortable and roomy. My daughter really likes the captain’s seats in the back. I am very happy with the Highlander and plan to have it for many years.
Anonymous
Reviewed a 2019 Toyota Highlander on Sep 3, 2024
great combination of reliability, function and features and price. Has more than enough bells and whistles with great driveability and comfort
Dennis G
Reviewed a 2019 Toyota Limited AWD on Mar 27, 2025
Comfortable, strong and stylish. Plenty of room for wife's wheel chair, her and myself along with what ever else we need to transport. Did have a problem starting once after sitting 3 weeks unproven. Small portable starter was very handy, started right up. No issues since. Lot of safety reminders, clearance between you and car in front of you in cruse control, out of lane warning. Wish it had digital speed display. Nav works well. I have SiriusXM radio, killer sound.
Suzanne M
Reviewed a 2019 Toyota Highlander on Oct 11, 2024
It’s roomy, has all the bells and whistles. Nice smooth ride. Takes a little time to manipulate all the “bells and whistles”. Also aesthetically good .
2019 Toyota Highlander Trims
| Trim type | MSRP |
|---|---|
| Limited FWD | $42,930 |
| Limited Platinum AWD | $47,510 |
| LE AWD | $35,340 |
| SE AWD | $42,400 |
| Limited AWD | $44,390 |
| LE FWD | $33,880 |
| XLE FWD | $39,720 |
| XLE AWD | $41,180 |
2019 Toyota Highlander Price Trends
CarGurus tracks the prices of millions of used car listings every year. See how the average price of 2019 Toyota Highlander prices has changed over time.
See more price trends2019 Toyota Highlander Pricing Analysis: Chicago, IL Market Report
Pricing by Nearby Locations
Market Area: Chicago, IL
Key Insights
- Highest Price in South Bend: The average price for the Highlander in South Bend, IN ($27,028) suggests a premium due to potentially lower supply.
- Best Value in Lafayette: Lafayette, IN ($23,283) has the lowest average price, indicating it might be more price-sensitive or have higher inventory.
- Inventory Variability: The city of Aurora has the highest inventory with 184 listings, while Limited FWD and SE AWD trims show comparatively lower supply.
City-Level Pricing
| City | Total Listings | Avg Price |
|---|---|---|
| South Bend, IN | 157 | $27,028 |
| Kenosha, WI | 172 | $25,114 |
| Rockford, IL | 144 | $25,292 |
| Milwaukee, WI | 145 | $24,712 |
| Palatine, IL | 181 | $24,682 |
| Aurora, IL | 184 | $24,510 |
| Janesville, WI | 142 | $26,206 |
| Holland, MI | 160 | $24,950 |
| Kalamazoo, MI | 165 | $26,235 |
| Lafayette, IN | 171 | $23,283 |
Pricing by Trim Packages
Key Insights
- Popularity of XLE Trims: The XLE AWD trim is the most listed option with 222 listings, reflecting a strong preference for this configuration.
- Premium Pricing for Limited AWD: The Limited AWD trim has the highest MSRP at $44,390, indicating a significant markup for advanced features.
- Value in Base LE Trims: The LE AWD offers competitive pricing with just 75 listings, suggesting a good mix of features and value for consumers.
Trim-Level Details
| Trim | Listings | MSRP | Drivetrain | Engine |
|---|---|---|---|---|
| XLE AWD | 222 | $41,180 | AWD | 3.5L 295 hp V6 |
| XLE FWD | 57 | $39,720 | FWD | 3.5L 295 hp V6 |
| Limited AWD | 101 | $44,390 | AWD | 3.5L 295 hp V6 |
| LE FWD | 43 | $33,880 | FWD | 3.5L 295 hp V6 |
| LE AWD | 75 | $35,340 | AWD | 3.5L 295 hp V6 |
| Limited FWD | 28 | $42,930 | FWD | 3.5L 295 hp V6 |
| SE AWD | 23 | $42,400 | AWD | 3.5L 295 hp V6 |
| Limited Platinum AWD | 21 | $47,510 | AWD | 3.5L 295 hp V6 |
Pricing Analysis by Model Year
Key Insights
- New Models at a Premium: The 2026 Highlander shows a current average price of $50,925, reflecting a 10.9% increase over its MSRP, indicative of high demand for the latest model.
- Steep Depreciation for Older Models: The 2015 Highlander has the lowest current average price at $16,624, indicating a depreciation of -44.1% against its original MSRP.
- Stable Value in Recent Years: The 2022 model maintains a relatively modest depreciation of only -3.4% compared to MSRP, suggesting solid value retention over a shorter period.
Model Year Pricing
| Model Year | Original MSRP | Avg Price | Price vs MSRP |
|---|---|---|---|
| 2026 Toyota Highlander | $45,870 | $50,925 | +10.9% |
| 2025 Toyota Highlander | $40,320 | $42,071 | +4.4% |
| 2024 Toyota Highlander | $39,270 | $35,080 | -10.3% |
| 2023 Toyota Highlander | $36,620 | $35,689 | -2.5% |
| 2022 Toyota Highlander | $35,855 | $34,455 | -3.9% |
| 2021 Toyota Highlander | $35,085 | $29,676 | -15.5% |
| 2020 Toyota Highlander | $34,600 | $29,547 | -14.7% |
| 2018 Toyota Highlander | $31,230 | $23,179 | -25.7% |
| 2017 Toyota Highlander | $30,630 | $19,965 | -34.9% |
| 2016 Toyota Highlander | $30,490 | $19,820 | -34.9% |
| 2015 Toyota Highlander | $29,765 | $16,624 | -44.1% |
These recommendations are based on CarGurus' proprietary market data from May 28, 2026, CarGurus experts' opinions, and generative AI.
