Used Jeep Grand Cherokee Trailhawk 4WD for Sale in Chicago, IL

to
to

Filter Results

listing

Price

- Loading...
Includes Listings Without Available Pricing

Financing

Mileage

- Loading...

Delivery

Days on Market

- Loading...

Recent Listings

Vehicle History

Vehicle history data provided by Experian AutoCheck. This data, and any reliance on it, is subject to the AutoCheck Terms and Conditions and the CarGurus Terms of Use
Hide vehicles with:

Photos

Fuel Economy

- Loading...
()

Price Drops

Text Search

Add Similar Cars


2000 Jeep Grand Cherokee Laredo 4WD Review
by Roger

A fun SUV that will tow well and has good road manners.

Love this Jeep. With the 4.7 V8 it is spirited to drive. Tows the sled trailer with ease too. Selectrac 4 wheel drive is good for anything you can throw at it. Will do 20mpg on the open road which is not too awful for a V8 four wheel drive. Peppy and smooth. I upgraded the TCM to the 545RFE unit and now have a 5 speed auto instead of the 4 spee...

First
Loading...
https://static.cargurus.com/images/forsale/2019/10/09/20/32/2017_jeep_grand_cherokee-pic-478300006421628405-152x114.jpeg

2017 Jeep Grand Cherokee Trailhawk 4WD Used Cars in St Charles, IL 60174

Good Deal
$2,248 BELOW
CarGurus IMV of $35,047

Price: $32,799

Mileage: 25,884

Location: St Charles, IL 60174

Average time on market: 30 days Certified Pre-Owned: Yes Transmission: 8-Speed Automatic Color: Black Description: Used 2017 Jeep Grand Cherokee Trailhawk 4WD for sale - $32,799, 25,884 miles with Backup Camera, Alloy Wheels
Avg. Dealer Rating: (72 reviews) "The vehicle that I went to see was sol but they assured me that they could find me another. Which they did. I am happy that I bought the vehicle from them. I enjoy driving it everyday. "
https://static.cargurus.com/images/forsale/2018/08/22/16/26/2018_jeep_grand_cherokee-pic-1997309977350972691-152x114.jpeg

2017 Jeep Grand Cherokee Trailhawk 4WD Used Cars in Skokie, IL 60077

Good Deal
$2,348 BELOW
CarGurus IMV of $31,848

Price: $29,500

Mileage: 42,038

Location: Skokie, IL 60077

Average time on market: 30 days Certified Pre-Owned: Yes Transmission: 8-Speed Automatic Color: Gray Description: Used 2017 Jeep Grand Cherokee Trailhawk 4WD for sale - $29,500, 42,038 miles with Backup Camera, Alloy Wheels
Avg. Dealer Rating: (82 reviews) "Made an appointment to see a car, ignored the reviews and sure enough got there and supposedly within the 2 days the manager assured us the car will be there..it wasnt... so got us in the door and tried to make offers on other cars which were very tempting but we didnt buy...overall service was good but they will initially try just to get you through the door. "
https://static.cargurus.com/images/forsale/2019/09/28/04/15/2017_jeep_grand_cherokee-pic-7707685048638039641-152x114.jpeg

2017 Jeep Grand Cherokee Trailhawk 4WD Used Cars in Chicago, IL 60659

Good Deal
$1,751 BELOW
CarGurus IMV of $29,694

Price: $27,943

Mileage: 68,650

Location: Chicago, IL 60659

Average time on market: 30 days Certified Pre-Owned: No Transmission: 8-Speed Automatic Color: Red Description: Used 2017 Jeep Grand Cherokee Trailhawk 4WD for sale - $27,943, 68,650 miles with Leather Seats, Backup Camera, Sunroof/Moonroof, Remote Start, Navigation System, Alloy Wheels
Avg. Dealer Rating: (25 reviews) "I don’t any experience with the dealer yet!"
https://static.cargurus.com/images/forsale/2019/07/16/10/33/2017_jeep_grand_cherokee-pic-8678833655387344347-152x114.jpeg

2017 Jeep Grand Cherokee Trailhawk 4WD Used Cars in Downers Grove, IL 60515

Good Deal
$990 BELOW
CarGurus IMV of $32,490

Price: $31,500

Mileage: 38,922

Location: Downers Grove, IL 60515

Average time on market: 30 days Certified Pre-Owned: No Transmission: 8-Speed Automatic Color: Granite Crystal Metallic Clearcoat Description: Used 2017 Jeep Grand Cherokee Trailhawk 4WD for sale - $31,500, 38,922 miles with Leather Seats, Sunroof/Moonroof, Customer Preferred Package, Power Package, Navigation System, Adaptive Cruise Control, Alloy Wheels, Technology Package, Heat Package, Premium Package, Tow Package, Premium Sound Package, Climate Package, Luxury Package, Bluetooth, Memory Package, Backup Camera, Sound Package, Convenience Package
Avg. Dealer Rating: (76 reviews) "They were fantastic! I purchased the car, they shipped it (from Chicago to Dallas), I had it is 2 days. I paid cash and they bent over backwards to help me. I don't know what else you could ask for in a car dealership."
https://static.cargurus.com/images/forsale/2019/08/19/08/35/2018_jeep_grand_cherokee-pic-5716669616631287676-152x114.jpeg

2018 Jeep Grand Cherokee Trailhawk 4WD Used Cars in Chicago, IL 60632

Fair Deal
$992 BELOW
CarGurus IMV of $34,149

Price: $33,157

Mileage: 20,503

Location: Chicago, IL 60632

Average time on market: 39 days Certified Pre-Owned: No Transmission: 8-Speed Automatic Color: Red Line Description: Used 2018 Jeep Grand Cherokee Trailhawk 4WD for sale - $33,157, 20,503 miles with Navigation System, Backup Camera, Quick Order Package
Avg. Dealer Rating: (8 reviews) "Returned my e-mail with the answers to my questions very promptly. Decision to purchase included driving seven hours each way. If this was a two to three hour drive I would have been all over it."
https://static.cargurus.com/images/forsale/2019/09/15/04/55/2019_jeep_grand_cherokee-pic-5823131084585568489-152x114.jpeg

2019 Jeep Grand Cherokee Trailhawk 4WD Used Cars in Elgin, IL 60120

Fair Deal
$652 BELOW
CarGurus IMV of $36,552

Price: $35,900

Mileage: 14,719

Location: Elgin, IL 60120

Average time on market: 28 days Certified Pre-Owned: No Transmission: 8-Speed Automatic Color: Diamond Black Description: Used 2019 Jeep Grand Cherokee Trailhawk 4WD for sale - $35,900, 14,719 miles with Backup Camera, Navigation System, Alloy Wheels, Quick Order Package
Avg. Dealer Rating: (12 reviews) "Great. Very polite and professional. "
https://static.cargurus.com/images/forsale/2019/09/03/21/48/2018_jeep_grand_cherokee-pic-1279266836525635333-152x114.jpeg

2018 Jeep Grand Cherokee Trailhawk 4WD Used Cars in Forest Park, IL 60130

Fair Deal
$827 BELOW
CarGurus IMV of $34,826

Price: $33,999

Mileage: 23,075

Location: Forest Park, IL 60130

Average time on market: 39 days Certified Pre-Owned: No Transmission: 8-Speed Automatic Color: Billet Silver Metallic Clearcoat Description: Used 2018 Jeep Grand Cherokee Trailhawk 4WD for sale - $33,999, 23,075 miles with Leather Seats, Sunroof/Moonroof, Navigation System, Alloy Wheels, Bluetooth, Backup Camera, Remote Start
Avg. Dealer Rating: (8 reviews) "Highly recommended. Ask for Eddie! He’s the man! "
https://static.cargurus.com/images/forsale/2019/06/19/11/48/2017_jeep_grand_cherokee-pic-3242725524270098517-152x114.jpeg

2017 Jeep Grand Cherokee Trailhawk 4WD Used Cars in Chicago, IL 60641

Fair Deal
$500 BELOW
CarGurus IMV of $35,494

Price: $34,994

Mileage: 15,601

Location: Chicago, IL 60641

Average time on market: 30 days Certified Pre-Owned: No Transmission: 8-Speed Automatic Color: Gray Description: Used 2017 Jeep Grand Cherokee Trailhawk 4WD for sale - $34,994, 15,601 miles with Sunroof/Moonroof, Navigation System, Alloy Wheels, Bluetooth, Backup Camera, Remote Start, Tow Package, Quick Order Package
Avg. Dealer Rating: (11 reviews) "They were quick to contact me. The salesperson (Frank) was friendly, professional and helpful."
https://static.cargurus.com/images/forsale/2019/09/05/11/07/2017_jeep_grand_cherokee-pic-9045234608229950459-152x114.jpeg

2017 Jeep Grand Cherokee Trailhawk 4WD Used Cars in Valparaiso, IN 46385

Fair Deal
$538 BELOW
CarGurus IMV of $33,762

Price: $33,224

Mileage: 22,633

Location: Valparaiso, IN 46385

Average time on market: 30 days Certified Pre-Owned: No Transmission: 8-Speed Automatic Color: Red Line Description: Used 2017 Jeep Grand Cherokee Trailhawk 4WD for sale - $33,224, 22,633 miles with Leather Seats, Sunroof/Moonroof, Navigation System, Alloy Wheels, Bluetooth, Backup Camera, Quick Order Package
Avg. Dealer Rating: (12 reviews) "Everyone was very nice and worked with us. We bought the car!"
https://static.cargurus.com/images/forsale/2019/09/30/23/18/2019_jeep_grand_cherokee-pic-3579830981212274480-152x114.jpeg

2019 Jeep Grand Cherokee Trailhawk 4WD Used Cars in Niles, IL 60714

Fair Deal
$555 BELOW
CarGurus IMV of $38,443

Price: $37,888

Mileage: 2,933

Location: Niles, IL 60714

Average time on market: 28 days Certified Pre-Owned: No Transmission: 8-Speed Automatic Color: Granite Crystal Metallic Clearcoat Description: Used 2019 Jeep Grand Cherokee Trailhawk 4WD for sale - $37,888, 2,933 miles with Bluetooth, Sunroof/Moonroof, Remote Start, Navigation System
Avg. Dealer Rating: (34 reviews) "While the listing price on your sight was way wrong I spoke to several knowledgeable people about Rangers pricing and will stay in touch as the market levels. Honest and straightforward."
https://static1.cargurus.com/gfx/cg/noImageAvailable_150x113.png

2018 Jeep Grand Cherokee Trailhawk 4WD Used Cars in Elmhurst, IL 60126

Fair Deal
$1,114 BELOW
CarGurus IMV of $36,514

Price: $35,400

Mileage: 15,326

Location: Elmhurst, IL 60126

Average time on market: 39 days Certified Pre-Owned: No Transmission: 8-Speed Automatic Color: Diamond Black Description: Used 2018 Jeep Grand Cherokee Trailhawk 4WD for sale - $35,400, 15,326 miles with Backup Camera, Sunroof/Moonroof, Navigation System, Adaptive Cruise Control, Quick Order Package
Avg. Dealer Rating: (60 reviews) "Helpful"
https://static.cargurus.com/images/forsale/2019/10/11/02/11/2017_jeep_grand_cherokee-pic-4634478741166034820-152x114.jpeg

2017 Jeep Grand Cherokee Trailhawk 4WD Used Cars in St Charles, IL 60174

Fair Deal
$471 BELOW
CarGurus IMV of $32,245

Price: $31,774

Mileage: 33,260

Location: St Charles, IL 60174

Average time on market: 30 days Certified Pre-Owned: No Transmission: 8-Speed Automatic Color: Redline 2 Coat Pearl Description: Used 2017 Jeep Grand Cherokee Trailhawk 4WD for sale - $31,774, 33,260 miles with Backup Camera, Alloy Wheels
Avg. Dealer Rating: (72 reviews) "People were very nice. Tried to raise the vehicle price almost $1500 over the advertised price. They did discount it, but after needless haggling. Finance guy was very straightforward and got us a great rate. Overall, not bad, just wish they were more honest and upfront about the pricing. "
https://static.cargurus.com/images/forsale/2019/10/04/23/27/2017_jeep_grand_cherokee-pic-1336035938481698532-152x114.jpeg

2017 Jeep Grand Cherokee Trailhawk 4WD Used Cars in Naperville, IL 60540

Fair Deal
$264 BELOW
CarGurus IMV of $32,741

Price: $32,477

Mileage: 36,741

Location: Naperville, IL 60540

Average time on market: 30 days Certified Pre-Owned: Yes Transmission: 8-Speed Automatic Color: Bright White Clearcoat Description: Used 2017 Jeep Grand Cherokee Trailhawk 4WD for sale - $32,477, 36,741 miles with Bluetooth, Backup Camera, Sunroof/Moonroof, Remote Start, Navigation System
Avg. Dealer Rating: (12 reviews) "Very good people to do business with, I will recommend this place."
https://static.cargurus.com/images/forsale/2019/10/01/18/00/2017_jeep_grand_cherokee-pic-1793027379405615167-152x114.jpeg

2017 Jeep Grand Cherokee Trailhawk 4WD Used Cars in Cedar Lake, IN 46303

Fair Deal
$74 ABOVE
CarGurus IMV of $32,403

Price: $32,477

Mileage: 34,261

Location: Cedar Lake, IN 46303

Average time on market: 30 days Certified Pre-Owned: No Transmission: 8-Speed Automatic Color: Rhino Clearcoat Description: Used 2017 Jeep Grand Cherokee Trailhawk 4WD for sale - $32,477, 34,261 miles with Leather Seats, Backup Camera, Sunroof/Moonroof, Remote Start, Alloy Wheels
Avg. Dealer Rating: (8 reviews) "Great place to buy a car."
https://static.cargurus.com/images/forsale/2019/08/09/23/11/2018_jeep_grand_cherokee-pic-2445132391783326909-152x114.jpeg

2018 Jeep Grand Cherokee Trailhawk 4WD Used Cars in Naperville, IL 60540

Fair Deal
$89 BELOW
CarGurus IMV of $34,766

Price: $34,677

Mileage: 23,532

Location: Naperville, IL 60540

Average time on market: 39 days Certified Pre-Owned: No Transmission: 8-Speed Automatic Color: Diamond Black Crystal Pearlcoat Description: Used 2018 Jeep Grand Cherokee Trailhawk 4WD for sale - $34,677, 23,532 miles with Bluetooth, Backup Camera, Remote Start, Navigation System
Avg. Dealer Rating: (12 reviews) "The response time and email service was impeccable. On sight-They do not allow any negotiations, even though I left before they could even start. Justin stared me down in my car as I was waiting for the rain to let up, started asking me questions before I could get out of the rain. Brought me to a desk without asking if I had spoke with anyone, asked if we have a sale before I even saw the vehicle. He contiguously asked if we had a sale at the end of each topic. He insulted me directly, reluctantly answered my questions, & was not educated on the vehicle. He attempted to have me sign before we talked numbers & had my answers. He even brought the sales manager Johnny over before answering my questions. Johnny was just as rude, they assumed they could bully me into buying a car. The most pressure I have ever gotten from a dealership. I left after 30 minutes, and that is including a test drive. "
Please wait ...
Please wait ...

Filter your search criteria!

A large number of listings matched your criteria. You are seeing the top 2,000 listings.

Used Jeep Grand Cherokee Trailhawk 4WD By Year

Vehicle Deals Starting Price Total Available
2019 Jeep Grand Cherokee Trailhawk 4WD 11 Great Deals $33,495 883 listings
2018 Jeep Grand Cherokee Trailhawk 4WD 11 Great Deals $30,489 213 listings
2017 Jeep Grand Cherokee Trailhawk 4WD 13 Great Deals $24,573 317 listings

Why Use CarGurus?

We'll help you find great deals among the millions of vehicles available nationwide on CarGurus, and we'll provide you with dealer reviews and vehicle history for each one. After all, over 30 million shoppers use CarGurus to find great deals on used cars and new cars in their area. And when it's time to get rid of your old ride, sell your car simply and securely on CarGurus.

Once you're ready to narrow down your search results, go ahead and filter by price, mileage, transmission, trim, days on lot, drivetrain, color, engine, options, and deal ratings. And if you only want to see cars with a single owner, recent price drops, photos, or available financing, our filters can help with that too.