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Used Jeep in Chicago, IL for Sale

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2014 Jeep Wrangler Unlimited Sahara

$21,998* 92K Miles


CarMax Hillside (Eisenhower Expy) In stock

Key Features
4WD/AWD, Alpine Sound System, Satellite Radio Ready, Tow Hitch, Running Boards, Auxiliary Audio Input
Location: CarMax Hillside (Eisenhower Expy) in Chicago, Illinois 60162
Description: Used 2014 Jeep Wrangler Unlimited Sahara for sale - $21,998, 91,485 miles with 4WD/AWD, Alpine Sound System, Satellite Radio Ready, Tow Hitch, Running Boards, Auxiliary Audio Input
Transmission: Automatic Color:White Interior Color: Black Average Vehicle Review: (4.714 reviews) I was so excited, I had a grand years ago and thought this was sporty lower cost option. I was so wrong. It rattles everywhere. I have had more recalls then I could have imagined, and overall it just seems small. I want to love it, and at the end of the day it's a car so I will keep driving it but it's not my favorite car I have ever owned. The nose is a huge blind spot I never noticed in the test drive but have caught myself almost hitting things because it's got a huge blind spot in the front.

2015 Jeep Compass Sport

$11,998* 98K Miles


CarMax Hillside (Eisenhower Expy) In stock

Key Features
4WD/AWD, Auxiliary Audio Input, Cruise Control, Alloy Wheels, Overhead Airbags, Traction Control
Location: CarMax Hillside (Eisenhower Expy) in Chicago, Illinois 60162
Description: Used 2015 Jeep Compass Sport for sale - $11,998, 97,690 miles with 4WD/AWD, Auxiliary Audio Input, Cruise Control, Alloy Wheels, Overhead Airbags, Traction Control
Transmission: Automatic Color:Black Interior Color: Black Average Vehicle Review: (4.2 reviews) This Wrangler had a brand-new feeling. It was several thousand dollars lower in cost than an actual brand-new Jeep. Jeep Wrangler came with hard top but easily was converted to a convertible with after-market soft top for the summer. Great snow vehicle and great summer vehicle.

2019 Jeep Grand Cherokee Limited

$31,998* 22K Miles


CarMax Hillside (Eisenhower Expy) In stock

Key Features
Power Liftgate/DeckLid, 4WD/AWD, Leather Seats, Satellite Radio Ready, Parking Sensors, Rear View Camera
Location: CarMax Hillside (Eisenhower Expy) in Chicago, Illinois 60162
Description: Used 2019 Jeep Grand Cherokee Limited for sale - $31,998, 21,554 miles with Power Liftgate/DeckLid, 4WD/AWD, Leather Seats, Satellite Radio Ready, Parking Sensors, Rear View Camera
Transmission: Automatic Color:Black Interior Color: Black Average Vehicle Review: (5 reviews) Appears to be reliable. Fuel economy bearable. Capable of modest towing. Sure footed (can do mild off-roading). In a nutshell, it is quite a bit of vehicle for the price I paid in today's market. While I'm not a fan of electronic automatics, this one seems to shift in a sensible fashion and with no strange anomalies so far. I have already taken the vehicle on a 3k mile road trip, camping out of the back of it for 4 of the 7 days I was on the road and it performed admirably. With 1000 pounds of me and my gear in it and ON it (I've added rood racks), I got 16mpg overall, including some dirt driving and HARD pushing it hard interstates. In normal use with just me and my lady aboard it gets every bit of the 23mpg claimed by Jeep.

2019 Jeep Compass Trailhawk

$20,998* 35K Miles


CarMax Hillside (Eisenhower Expy) In stock

Key Features
4WD/AWD, Satellite Radio Ready, Rear View Camera, Auxiliary Audio Input, Cruise Control, Alloy Wheels
Location: CarMax Hillside (Eisenhower Expy) in Chicago, Illinois 60162
Description: Used 2019 Jeep Compass Trailhawk for sale - $20,998, 34,424 miles with 4WD/AWD, Satellite Radio Ready, Rear View Camera, Auxiliary Audio Input, Cruise Control, Alloy Wheels
Transmission: Automatic Color:Silver Interior Color: Black Average Vehicle Review: (0 reviews)

2019 Jeep Compass Trailhawk

$20,998* 34K Miles


CarMax Hillside (Eisenhower Expy) In stock

Key Features
4WD/AWD, Satellite Radio Ready, Rear View Camera, Auxiliary Audio Input, Cruise Control, Alloy Wheels
Location: CarMax Hillside (Eisenhower Expy) in Chicago, Illinois 60162
Description: Used 2019 Jeep Compass Trailhawk for sale - $20,998, 33,221 miles with 4WD/AWD, Satellite Radio Ready, Rear View Camera, Auxiliary Audio Input, Cruise Control, Alloy Wheels
Transmission: Automatic Color:Red Interior Color: Black Average Vehicle Review: (0 reviews)

2019 Jeep Compass Trailhawk

$20,998* 28K Miles


CarMax Hillside (Eisenhower Expy) In stock

Key Features
4WD/AWD, Satellite Radio Ready, Rear View Camera, Auxiliary Audio Input, Cruise Control, Alloy Wheels
Location: CarMax Hillside (Eisenhower Expy) in Chicago, Illinois 60162
Description: Used 2019 Jeep Compass Trailhawk for sale - $20,998, 27,091 miles with 4WD/AWD, Satellite Radio Ready, Rear View Camera, Auxiliary Audio Input, Cruise Control, Alloy Wheels
Transmission: Automatic Color:Silver Interior Color: Black Average Vehicle Review: (0 reviews)

2019 Jeep Cherokee Latitude

$19,998* 28K Miles


CarMax Hillside (Eisenhower Expy) In stock

Key Features
Cold Weather Package, 4WD/AWD, Rear View Camera, Front Seat Heaters, Auxiliary Audio Input, Cruise Control
Location: CarMax Hillside (Eisenhower Expy) in Chicago, Illinois 60162
Description: Used 2019 Jeep Cherokee Latitude for sale - $19,998, 27,962 miles with Cold Weather Package, 4WD/AWD, Rear View Camera, Front Seat Heaters, Auxiliary Audio Input, Cruise Control
Transmission: Automatic Color:White Interior Color: Black Average Vehicle Review: (4.667 reviews)

2019 Jeep Compass Trailhawk

$23,998* 22K Miles


CarMax Hillside (Eisenhower Expy) In stock

Key Features
Cold Weather Package, Power Liftgate/DeckLid, 4WD/AWD, Satellite Radio Ready, Parking Sensors, Rear View Camera
Location: CarMax Hillside (Eisenhower Expy) in Chicago, Illinois 60162
Description: Used 2019 Jeep Compass Trailhawk for sale - $23,998, 21,092 miles with Cold Weather Package, Power Liftgate/DeckLid, 4WD/AWD, Satellite Radio Ready, Parking Sensors, Rear View Camera
Transmission: Automatic Color:Silver Interior Color: Black Average Vehicle Review: (0 reviews)

2015 Jeep Grand Cherokee Summit

$25,998* 50K Miles


CarMax Hillside (Eisenhower Expy) In stock

Key Features
Power Liftgate/DeckLid, Auto Cruise Control, 4WD/AWD, Leather Seats, Harman Kardon Sound, Satellite Radio Ready
Location: CarMax Hillside (Eisenhower Expy) in Chicago, Illinois 60162
Description: Used 2015 Jeep Grand Cherokee Summit for sale - $25,998, 49,092 miles with Power Liftgate/DeckLid, Auto Cruise Control, 4WD/AWD, Leather Seats, Harman Kardon Sound, Satellite Radio Ready
Transmission: Automatic Color:Gray Interior Color: Black Average Vehicle Review: (4.655 reviews)

2019 Jeep Compass Limited

$19,998* 32K Miles


CarMax Hillside (Eisenhower Expy) In stock

Key Features
Leather Seats, Satellite Radio Ready, Rear View Camera, Front Seat Heaters, Auxiliary Audio Input, Cruise Control
Location: CarMax Hillside (Eisenhower Expy) in Chicago, Illinois 60162
Description: Used 2019 Jeep Compass Limited for sale - $19,998, 31,981 miles with Leather Seats, Satellite Radio Ready, Rear View Camera, Front Seat Heaters, Auxiliary Audio Input, Cruise Control
Transmission: Automatic Color:White Interior Color: Black Average Vehicle Review: (0 reviews)

2019 Jeep Compass Limited

$19,998* 27K Miles


CarMax Hillside (Eisenhower Expy) In stock

Key Features
Leather Seats, Satellite Radio Ready, Rear View Camera, Front Seat Heaters, Auxiliary Audio Input, Cruise Control
Location: CarMax Hillside (Eisenhower Expy) in Chicago, Illinois 60162
Description: Used 2019 Jeep Compass Limited for sale - $19,998, 26,691 miles with Leather Seats, Satellite Radio Ready, Rear View Camera, Front Seat Heaters, Auxiliary Audio Input, Cruise Control
Transmission: Automatic Color:White Interior Color: Black Average Vehicle Review: (0 reviews)

2018 Jeep Grand Cherokee Limited

$27,998* 38K Miles


CarMax Hillside (Eisenhower Expy) In stock

Key Features
Power Liftgate/DeckLid, 4WD/AWD, Leather Seats, Satellite Radio Ready, Parking Sensors, Rear View Camera
Location: CarMax Hillside (Eisenhower Expy) in Chicago, Illinois 60162
Description: Used 2018 Jeep Grand Cherokee Limited for sale - $27,998, 37,168 miles with Power Liftgate/DeckLid, 4WD/AWD, Leather Seats, Satellite Radio Ready, Parking Sensors, Rear View Camera
Transmission: Automatic Color:Black Interior Color: Black Average Vehicle Review: (4.667 reviews)

2018 Jeep Wrangler All-New Unlimited Rubicon

$43,998* 11K Miles


CarMax Hillside (Eisenhower Expy) In stock

Key Features
Cold Weather Package, 4WD/AWD, Leather Seats, Alpine Sound System, Satellite Radio Ready, Parking Sensors
Location: CarMax Hillside (Eisenhower Expy) in Chicago, Illinois 60162
Description: Used 2018 Jeep Wrangler All-New Unlimited Rubicon for sale - $43,998, 10,217 miles with Cold Weather Package, 4WD/AWD, Leather Seats, Alpine Sound System, Satellite Radio Ready, Parking Sensors
Transmission: Manual 6 Speed Color:Orange Interior Color: Black Average Vehicle Review: (4.75 reviews)

2018 Jeep Grand Cherokee Altitude

$29,998* 27K Miles


CarMax Hillside (Eisenhower Expy) In stock

Key Features
Power Liftgate/DeckLid, 4WD/AWD, Leather & Suede Seats, Satellite Radio Ready, Parking Sensors, Rear View Camera
Location: CarMax Hillside (Eisenhower Expy) in Chicago, Illinois 60162
Description: Used 2018 Jeep Grand Cherokee Altitude for sale - $29,998, 26,075 miles with Power Liftgate/DeckLid, 4WD/AWD, Leather & Suede Seats, Satellite Radio Ready, Parking Sensors, Rear View Camera
Transmission: Automatic Color:White Interior Color: Black Average Vehicle Review: (4.667 reviews)

2018 Jeep Grand Cherokee Altitude

$29,998* 23K Miles


CarMax Hillside (Eisenhower Expy) In stock

Key Features
Power Liftgate/DeckLid, 4WD/AWD, Leather & Suede Seats, Satellite Radio Ready, Parking Sensors, Rear View Camera
Location: CarMax Hillside (Eisenhower Expy) in Chicago, Illinois 60162
Description: Used 2018 Jeep Grand Cherokee Altitude for sale - $29,998, 22,303 miles with Power Liftgate/DeckLid, 4WD/AWD, Leather & Suede Seats, Satellite Radio Ready, Parking Sensors, Rear View Camera
Transmission: Automatic Color:Black Interior Color: Black Average Vehicle Review: (4.667 reviews)

2016 Jeep Grand Cherokee High Altitude

$29,998* 39K Miles


CarMax Hillside (Eisenhower Expy) In stock

Key Features
Technology Package, Power Liftgate/DeckLid, Auto Cruise Control, 4WD/AWD, Leather Seats, Harman Kardon Sound
Location: CarMax Hillside (Eisenhower Expy) in Chicago, Illinois 60162
Description: Used 2016 Jeep Grand Cherokee High Altitude for sale - $29,998, 38,388 miles with Technology Package, Power Liftgate/DeckLid, Auto Cruise Control, 4WD/AWD, Leather Seats, Harman Kardon Sound
Transmission: Automatic Color:Red Interior Color: Black Average Vehicle Review: (5 reviews)

2018 Jeep Cherokee Overland

$24,998* 28K Miles


CarMax Hillside (Eisenhower Expy) In stock

Key Features
Power Liftgate/DeckLid, Auto Cruise Control, 4WD/AWD, Leather Seats, Satellite Radio Ready, Parking Sensors
Location: CarMax Hillside (Eisenhower Expy) in Chicago, Illinois 60162
Description: Used 2018 Jeep Cherokee Overland for sale - $24,998, 27,128 miles with Power Liftgate/DeckLid, Auto Cruise Control, 4WD/AWD, Leather Seats, Satellite Radio Ready, Parking Sensors
Transmission: Automatic Color:Black Interior Color: Black Average Vehicle Review: (4 reviews)

2018 Jeep Grand Cherokee Altitude

$28,998* 21K Miles


CarMax Hillside (Eisenhower Expy) In stock

Key Features
Power Liftgate/DeckLid, 4WD/AWD, Leather & Suede Seats, Satellite Radio Ready, Parking Sensors, Navigation System
Location: CarMax Hillside (Eisenhower Expy) in Chicago, Illinois 60162
Description: Used 2018 Jeep Grand Cherokee Altitude for sale - $28,998, 20,567 miles with Power Liftgate/DeckLid, 4WD/AWD, Leather & Suede Seats, Satellite Radio Ready, Parking Sensors, Navigation System
Transmission: Automatic Color:White Interior Color: Black Average Vehicle Review: (4.667 reviews)

2018 Jeep Grand Cherokee Laredo

$24,998* 26K Miles


CarMax Hillside (Eisenhower Expy) In stock

Key Features
4WD/AWD, Satellite Radio Ready, Parking Sensors, Rear View Camera, Navigation System, Auxiliary Audio Input
Location: CarMax Hillside (Eisenhower Expy) in Chicago, Illinois 60162
Description: Used 2018 Jeep Grand Cherokee Laredo for sale - $24,998, 25,083 miles with 4WD/AWD, Satellite Radio Ready, Parking Sensors, Rear View Camera, Navigation System, Auxiliary Audio Input
Transmission: Automatic Color:Black Interior Color: Black Average Vehicle Review: (4.667 reviews)

2018 Jeep Grand Cherokee Laredo

$27,998* 21K Miles


CarMax Hillside (Eisenhower Expy) In stock

Key Features
Power Liftgate/DeckLid, 4WD/AWD, Leather Seats, Satellite Radio Ready, Parking Sensors, Rear View Camera
Location: CarMax Hillside (Eisenhower Expy) in Chicago, Illinois 60162
Description: Used 2018 Jeep Grand Cherokee Laredo for sale - $27,998, 20,383 miles with Power Liftgate/DeckLid, 4WD/AWD, Leather Seats, Satellite Radio Ready, Parking Sensors, Rear View Camera
Transmission: Automatic Color:White Interior Color: Black Average Vehicle Review: (4.667 reviews)

2018 Jeep Cherokee Overland

$26,998* 19K Miles


CarMax Hillside (Eisenhower Expy) In stock

Key Features
Power Liftgate/DeckLid, Auto Cruise Control, 4WD/AWD, Leather Seats, Satellite Radio Ready, Parking Sensors
Location: CarMax Hillside (Eisenhower Expy) in Chicago, Illinois 60162
Description: Used 2018 Jeep Cherokee Overland for sale - $26,998, 18,615 miles with Power Liftgate/DeckLid, Auto Cruise Control, 4WD/AWD, Leather Seats, Satellite Radio Ready, Parking Sensors
Transmission: Automatic Color:Gray Interior Color: Black Average Vehicle Review: (4 reviews)

2018 Jeep Compass Limited

$19,998* 28K Miles


CarMax Hillside (Eisenhower Expy) In stock

Key Features
4WD/AWD, Leather Seats, Satellite Radio Ready, Navigation System, Front Seat Heaters, Auxiliary Audio Input
Location: CarMax Hillside (Eisenhower Expy) in Chicago, Illinois 60162
Description: Used 2018 Jeep Compass Limited for sale - $19,998, 27,388 miles with 4WD/AWD, Leather Seats, Satellite Radio Ready, Navigation System, Front Seat Heaters, Auxiliary Audio Input
Transmission: Automatic Color:Gray Interior Color: Black Average Vehicle Review: (3 reviews)

2016 Jeep Grand Cherokee High Altitude

$28,998* 29K Miles


CarMax Hillside (Eisenhower Expy) In stock

Key Features
Power Liftgate/DeckLid, Auto Cruise Control, 4WD/AWD, Leather Seats, Satellite Radio Ready, Parking Sensors
Location: CarMax Hillside (Eisenhower Expy) in Chicago, Illinois 60162
Description: Used 2016 Jeep Grand Cherokee High Altitude for sale - $28,998, 28,432 miles with Power Liftgate/DeckLid, Auto Cruise Control, 4WD/AWD, Leather Seats, Satellite Radio Ready, Parking Sensors
Transmission: Automatic Color:Black Interior Color: Black Average Vehicle Review: (5 reviews)

2018 Jeep Compass Latitude

$18,998* 24K Miles


CarMax Hillside (Eisenhower Expy) In stock

Key Features
Cold Weather Package, 4WD/AWD, Satellite Radio Ready, Parking Sensors, Rear View Camera, Navigation System
Location: CarMax Hillside (Eisenhower Expy) in Chicago, Illinois 60162
Description: Used 2018 Jeep Compass Latitude for sale - $18,998, 23,324 miles with Cold Weather Package, 4WD/AWD, Satellite Radio Ready, Parking Sensors, Rear View Camera, Navigation System
Transmission: Automatic Color:White Interior Color: Black Average Vehicle Review: (3 reviews)

Reviews for Jeep

Overall Rating

4.4 out of 5(2,317 reviews)

What the doctor ordered so far

Appears to be reliable. Fuel economy bearable. Capable of modest towing. Sure footed (can do mild off-roading). In a nutshell, it is quite a bit of vehicle for the price I paid in today's market. While I'm not a fan of electronic automatics, this one seems to shift in a sensible fashion and with no strange anomalies so far. I have already taken the vehicle on a 3k mile road trip, camping out of the back of it for 4 of the 7 days I was on the road and it performed admirably. With 1000 pounds of me and my gear in it and ON it (I've added rood racks), I got 16mpg overall, including some dirt driving and HARD pushing it hard interstates. In normal use with just me and my lady aboard it gets every bit of the 23mpg claimed by Jeep.

- Mike Lee, 2013 Jeep Grand Cherokee

Low-mileage Jeep for less than new

This Wrangler had a brand-new feeling. It was several thousand dollars lower in cost than an actual brand-new Jeep. Jeep Wrangler came with hard top but easily was converted to a convertible with after-market soft top for the summer. Great snow vehicle and great summer vehicle.

- Jerry Miller, 2013 Jeep Wrangler

I thought I loved it.

I was so excited, I had a grand years ago and thought this was sporty lower cost option. I was so wrong. It rattles everywhere. I have had more recalls then I could have imagined, and overall it just seems small. I want to love it, and at the end of the day it's a car so I will keep driving it but it's not my favorite car I have ever owned. The nose is a huge blind spot I never noticed in the test drive but have caught myself almost hitting things because it's got a huge blind spot in the front.

- R R, 2014 Jeep Cherokee

This price does not include tax, title, and tags. Additional fees may also apply depending on the state of purchase.