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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 would not recommend this car to a friend because I find it hard to drive. It has larger blind spots than I realized when I test drove the car. A bigger issue is its reliability. It seems to have electronic issues. It's been in the shop 3 weeks out of the 14 that I have owned the car. If I hadn't bought the warranty, I would have been walking for those 3 weeks. The warranty entitles me to a loaner car when my car is in the shop, but it has sometimes been a hassle to get the loaner car. Eventually I get a loaner, but I traded in an 11 year old car because of dependability issues. At this point I miss my old car. I'm not sure I will be keeping this car very long, and I'm sure I'm going to be out quite a bit when I trade it.

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) Love my jeep, loved my last one too. TERRIBLE gas mileage, but so much fun. Has the newer soft top mechanism which allows me to have fingernails (female jeep issues), but leaks. Leaks in the rear behind the back seat and passenger seat, but I don't sit there. Keep my extra raincoat, hat and first aid kit in a space bag now.

2019 Jeep Compass Trailhawk

$20,998* 39K 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, 38,214 miles with 4WD/AWD, Satellite Radio Ready, Rear View Camera, Auxiliary Audio Input, Cruise Control, Alloy Wheels
Transmission: Automatic Color:Gray Interior Color: Black Average Vehicle Review: (0 reviews) First of all the car is a four cyclinder. Slow as molasses. It's loud and the vehicle is really compact inside. I bought it used with 19,000 miles on it. And it's in the shop. Something about he temperature gauge. The check engine light goes on which disables the restore start. It's like -5 outside and really could use that option right now. Had to wait a week to get into the Jeep dealer to be serviced and now have waited over a week for the part to come in. Very unhappy right now. I hear a knocking noise but the dealer service department says he doesn't hear anything. The sound comes and goes and drives me nuts cuz apparently no one but me hears it. Weird huh? Also, it's not quiet at all. You can hear outside noise. Trading in very soon.

2015 Jeep Compass Sport

$13,599* 80K Miles


CarMax Hillside (Eisenhower Expy) In stock

Key Features
4WD/AWD, Tow Hitch, Auxiliary Audio Input, Cruise Control, Alloy Wheels, Overhead Airbags
Location: CarMax Hillside (Eisenhower Expy) in Chicago, Illinois 60162
Description: Used 2015 Jeep Compass Sport for sale - $13,599, 79,613 miles with 4WD/AWD, Tow Hitch, Auxiliary Audio Input, Cruise Control, Alloy Wheels, Overhead Airbags
Transmission: Automatic Color:Black Interior Color: Black Average Vehicle Review: (4.2 reviews)

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)

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

$28,998* 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 - $28,998, 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)
New Arrival

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)

Reviews for Jeep

Overall Rating

4.4 out of 5(2,317 reviews)

So-so car.

I would not recommend this car to a friend because I find it hard to drive. It has larger blind spots than I realized when I test drove the car. A bigger issue is its reliability. It seems to have electronic issues. It's been in the shop 3 weeks out of the 14 that I have owned the car. If I hadn't bought the warranty, I would have been walking for those 3 weeks. The warranty entitles me to a loaner car when my car is in the shop, but it has sometimes been a hassle to get the loaner car. Eventually I get a loaner, but I traded in an 11 year old car because of dependability issues. At this point I miss my old car. I'm not sure I will be keeping this car very long, and I'm sure I'm going to be out quite a bit when I trade it.

- C. O., 2014 Jeep Cherokee

Hate this car

First of all the car is a four cyclinder. Slow as molasses. It's loud and the vehicle is really compact inside. I bought it used with 19,000 miles on it. And it's in the shop. Something about he temperature gauge. The check engine light goes on which disables the restore start. It's like -5 outside and really could use that option right now. Had to wait a week to get into the Jeep dealer to be serviced and now have waited over a week for the part to come in. Very unhappy right now. I hear a knocking noise but the dealer service department says he doesn't hear anything. The sound comes and goes and drives me nuts cuz apparently no one but me hears it. Weird huh? Also, it's not quiet at all. You can hear outside noise. Trading in very soon.

- Jacqueline S, 2016 Jeep Cherokee

It's a jeep thing

Love my jeep, loved my last one too. TERRIBLE gas mileage, but so much fun. Has the newer soft top mechanism which allows me to have fingernails (female jeep issues), but leaks. Leaks in the rear behind the back seat and passenger seat, but I don't sit there. Keep my extra raincoat, hat and first aid kit in a space bag now.

- Say Anne, 2013 Jeep Wrangler

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