Used 2019 Toyota Highlander for Sale near Chicago, IL
185 results
CarGurus Analysis:
2019 Toyota Highlander
With 179 currently listed for sale near Chicago, IL and an average price of $24,816.00, 29.6% 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.
98.3% of 2019 Highlander models on CarGurus are accident-free.
The 2019 Toyota Highlander offers impressive spaciousness and comfort, making it a family-friendly choice with excellent safety ratings.
CarGurus Analysis: 2019 Toyota Highlander
Summary
With 179 currently listed for sale near Chicago, IL and an average price of $24,816.00, 29.6% 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.
98.3% of 2019 Highlander models on CarGurus are accident-free.
The 2019 Toyota Highlander offers impressive spaciousness and comfort, making it a family-friendly choice with excellent safety ratings.
Why it stands out
The 2019 Toyota Highlander impresses with its blend of comfort, capability, and safety. Known for its spacious interior, the Highlander provides a smooth ride suitable for families, making it a popular choice among midsize SUVs. Key features include a robust suite of standard safety technologies, which have consistently earned it high ratings from safety organizations. While it may not be the most thrilling drive due to its soft suspension and uncommunicative steering, it excels in reliability and versatility. The Highlander's ability to comfortably accommodate up to seven passengers with ample cargo space gives it a strong edge in the competitive SUV market.
Other model years to consider
- Average price: $35,589.00
- Good/great deal percentage: 63.0%
- User rating: 5 / 5
- Total listings: 184
- Average price: $35,287.00
- Good/great deal percentage: 71.3%
- User rating: 4.67 / 5
- Total listings: 202
- Average price: $34,688.00
- Good/great deal percentage: 68.1%
- User rating: 4.44 / 5
- Total listings: 207
This analysis is based on CarGurus' proprietary market data from April 14, 2026, CarGurus experts' opinions, and generative AI.
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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.
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