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Used Chrysler 300 in Chicago, IL for Sale

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2018 Chrysler 300 S

$23,998* 34K Miles


CarMax Hillside (Eisenhower Expy) In stock

Key Features
4WD/AWD, Leather Seats, Alpine Sound System, Parking Sensors, Rear View Camera, Navigation System
Location: CarMax Hillside (Eisenhower Expy) in Chicago, Illinois 60162
Description: Used 2018 Chrysler 300 S for sale - $23,998, 33,080 miles with 4WD/AWD, Leather Seats, Alpine Sound System, Parking Sensors, Rear View Camera, Navigation System
Transmission: Automatic Color:White Interior Color: Black Average Vehicle Review: (5 reviews) THE 2005 CHRYSLER 300 IS CERTAINLY A TOP OF THE LINE VEHICLE. IT WAS TRULY DESIGNED FOR PEOPLE OF ALL SHAPES, AND LENGTHS, AND THE SPACIOUS STYLE ACCOMODATES THE NEEDS FOR A FAMILY OF FOUR. ALTHOUGH, THE 2005 IS WONDERFUL, THE DESIGNER SPECIALIST OF THE 2012 CHRYSLER 300 GAVE US SOMETHING TO LOOK FORWARD TO. WE WOULD DEFINATELY PURCHASE ANOTHER CHRYSLER WITH THE 2012 IN MIND. IT IS BY FAR THE MOST PHENOMINAL VEHICLE ON THE MARKET. GO...............CHRYSLER.

2016 Chrysler 300 S Alloy Edition

$22,998* 30K Miles


CarMax Hillside (Eisenhower Expy) In stock

Key Features
4WD/AWD, Leather Seats, Parking Sensors, Rear View Camera, Navigation System, Front Seat Heaters
Location: CarMax Hillside (Eisenhower Expy) in Chicago, Illinois 60162
Description: Used 2016 Chrysler 300 S Alloy Edition for sale - $22,998, 29,357 miles with 4WD/AWD, Leather Seats, Parking Sensors, Rear View Camera, Navigation System, Front Seat Heaters
Transmission: Automatic Color:Black Interior Color: Black Average Vehicle Review: (4.563 reviews) After owning over 35 cars in my lifetime, this is "the best" all season vehicle I have ever owned. With the Hemi engine (which I had tweaked w/434bhp) and AWD it can be driven in any kind of weather but like a sports car or Bentley. Standard with every option you can think of it's a fantastic purchase. I would take this car over any SUV which I have owned many. I get nearly 30 mpg on trips w/four cylinder deactivation, fantastic!!

2018 Chrysler 300 Touring

$19,998* 7K Miles


CarMax Hillside (Eisenhower Expy) In stock

Key Features
Rear View Camera, Satellite Radio Ready, Auxiliary Audio Input, Overhead Airbags, ABS Brakes, Alloy Wheels
Location: CarMax Hillside (Eisenhower Expy) in Chicago, Illinois 60162
Description: Used 2018 Chrysler 300 Touring for sale - $19,998, 6,012 miles with Rear View Camera, Satellite Radio Ready, Auxiliary Audio Input, Overhead Airbags, ABS Brakes, Alloy Wheels
Transmission: Automatic Color:White Interior Color: Black Average Vehicle Review: (5 reviews) This red car pictured, was actually my car. I loved this car, it was the 2nd Chrysler 300 limited I had. Actually when we took long road trips, it would get 30 MPG. I originally bought it, because it has the largest back seat of any car, being a realtor, I wanted my clients to be comfortable. Lot's of room , great to drive and just an all around great car. Only reason I sold it was to get a mini van for my 3 grandchildren's car seats. Highly recommend the 300.

2017 Chrysler 300 S

$21,998* 44K Miles


CarMax Hillside (Eisenhower Expy) In stock

Key Features
4WD/AWD, Leather Seats, Parking Sensors, Rear View Camera, Navigation System, Front Seat Heaters
Location: CarMax Hillside (Eisenhower Expy) in Chicago, Illinois 60162
Description: Used 2017 Chrysler 300 S for sale - $21,998, 43,061 miles with 4WD/AWD, Leather Seats, Parking Sensors, Rear View Camera, Navigation System, Front Seat Heaters
Transmission: Automatic Color:Gray Interior Color: Black Average Vehicle Review: (5 reviews)

2017 Chrysler 300 S

$22,998* 48K Miles


CarMax Schaumburg Free shipping • IL to IL

Key Features
4WD/AWD, Leather Seats, Parking Sensors, Rear View Camera, Navigation System, Front Seat Heaters
Location: CarMax Schaumburg in Chicago, Illinois 60173
Description: Used 2017 Chrysler 300 S for sale - $22,998, 47,119 miles with 4WD/AWD, Leather Seats, Parking Sensors, Rear View Camera, Navigation System, Front Seat Heaters
Transmission: Automatic Color:Black Interior Color: Black Average Vehicle Review: (5 reviews)

2017 Chrysler 300 Limited

$18,998* 26K Miles


CarMax Schaumburg Free shipping • IL to IL

Key Features
Leather Seats, Rear View Camera, Front Seat Heaters, Satellite Radio Ready, Auxiliary Audio Input, Overhead Airbags
Location: CarMax Schaumburg in Chicago, Illinois 60173
Description: Used 2017 Chrysler 300 Limited for sale - $18,998, 25,386 miles with Leather Seats, Rear View Camera, Front Seat Heaters, Satellite Radio Ready, Auxiliary Audio Input, Overhead Airbags
Transmission: Automatic Color:White Interior Color: Black Average Vehicle Review: (5 reviews)

2017 Chrysler 300 S

$22,998* 41K Miles


CarMax Naperville Free shipping • IL to IL

Key Features
4WD/AWD, Leather Seats, Parking Sensors, Rear View Camera, Navigation System, Front Seat Heaters
Location: CarMax Naperville in Naperville, Illinois 60563
Description: Used 2017 Chrysler 300 S for sale - $22,998, 40,722 miles with 4WD/AWD, Leather Seats, Parking Sensors, Rear View Camera, Navigation System, Front Seat Heaters
Transmission: Automatic Color:Gray Interior Color: Black Average Vehicle Review: (5 reviews)

2019 Chrysler 300 Touring

$20,998* 20K Miles


CarMax Glencoe (Edens Expy) Free shipping • IL to IL

Key Features
Convenience Package, 4WD/AWD, Rear View Camera, Satellite Radio Ready, Auxiliary Audio Input, Overhead Airbags
Location: CarMax Glencoe (Edens Expy) in Glencoe, Illinois 60022
Description: Used 2019 Chrysler 300 Touring for sale - $20,998, 19,106 miles with Convenience Package, 4WD/AWD, Rear View Camera, Satellite Radio Ready, Auxiliary Audio Input, Overhead Airbags
Transmission: Automatic Color:Black Interior Color: Black Average Vehicle Review: (4 reviews)

2019 Chrysler 300 Limited

$19,998* 46K Miles


CarMax Oak Lawn Free shipping • IL to IL

Key Features
Leather Seats, Alpine Sound System, Rear View Camera, Front Seat Heaters, A/C Seat(s), Satellite Radio Ready
Location: CarMax Oak Lawn in Chicago, Illinois 60453
Description: Used 2019 Chrysler 300 Limited for sale - $19,998, 45,510 miles with Leather Seats, Alpine Sound System, Rear View Camera, Front Seat Heaters, A/C Seat(s), Satellite Radio Ready
Transmission: Automatic Color:White Interior Color: Black Average Vehicle Review: (4 reviews)

2016 Chrysler 300 S

$21,998* 39K Miles


CarMax Oak Lawn Free shipping • IL to IL

Key Features
Premium Package, Leather Seats, Parking Sensors, Rear View Camera, Navigation System, Front Seat Heaters
Location: CarMax Oak Lawn in Chicago, Illinois 60453
Description: Used 2016 Chrysler 300 S for sale - $21,998, 38,997 miles with Premium Package, Leather Seats, Parking Sensors, Rear View Camera, Navigation System, Front Seat Heaters
Transmission: Automatic Color:Black Interior Color: Black Average Vehicle Review: (4.563 reviews)

2014 Chrysler 300 S

$17,998* 41K Miles


CarMax Tinley Park Free shipping • IL to IL

Key Features
Leather Seats, Rear View Camera, Navigation System, Front Seat Heaters, Panoramic Sunroof, Satellite Radio Ready
Location: CarMax Tinley Park in Chicago, Illinois 60477
Description: Used 2014 Chrysler 300 S for sale - $17,998, 40,159 miles with Leather Seats, Rear View Camera, Navigation System, Front Seat Heaters, Panoramic Sunroof, Satellite Radio Ready
Transmission: Automatic Color:White Interior Color: Black Average Vehicle Review: (4.539 reviews)

2019 Chrysler 300 S

$22,998* 31K Miles


CarMax Tinley Park Free shipping • IL to IL

Key Features
Leather Seats, Alpine Sound System, Rear View Camera, Front Seat Heaters, Satellite Radio Ready, Auxiliary Audio Input
Location: CarMax Tinley Park in Chicago, Illinois 60477
Description: Used 2019 Chrysler 300 S for sale - $22,998, 30,341 miles with Leather Seats, Alpine Sound System, Rear View Camera, Front Seat Heaters, Satellite Radio Ready, Auxiliary Audio Input
Transmission: Automatic Color:Gray Interior Color: Black Average Vehicle Review: (4 reviews)

2016 Chrysler 300 S

$20,998* 46K Miles


CarMax Tinley Park Free shipping • IL to IL

Key Features
Leather Seats, Rear View Camera, Navigation System, Front Seat Heaters, Panoramic Sunroof, Satellite Radio Ready
Location: CarMax Tinley Park in Chicago, Illinois 60477
Description: Used 2016 Chrysler 300 S for sale - $20,998, 45,020 miles with Leather Seats, Rear View Camera, Navigation System, Front Seat Heaters, Panoramic Sunroof, Satellite Radio Ready
Transmission: Automatic Color:Gray Interior Color: Black Average Vehicle Review: (4.563 reviews)

2018 Chrysler 300 Touring

$20,998* 10K Miles


CarMax Tinley Park Free shipping • IL to IL

Key Features
4WD/AWD, Rear View Camera, Satellite Radio Ready, Overhead Airbags, ABS Brakes, Alloy Wheels
Location: CarMax Tinley Park in Chicago, Illinois 60477
Description: Used 2018 Chrysler 300 Touring for sale - $20,998, 9,884 miles with 4WD/AWD, Rear View Camera, Satellite Radio Ready, Overhead Airbags, ABS Brakes, Alloy Wheels
Transmission: Automatic Color:Black Interior Color: Black Average Vehicle Review: (5 reviews)

2016 Chrysler 300 S

$22,998* 31K Miles


CarMax Merrillville Free shipping • IN to IL

Key Features
Premium Package, 4WD/AWD, Leather Seats, Parking Sensors, Rear View Camera, Navigation System
Location: CarMax Merrillville in Merrillville, Indiana 46410
Description: Used 2016 Chrysler 300 S for sale - $22,998, 30,908 miles with Premium Package, 4WD/AWD, Leather Seats, Parking Sensors, Rear View Camera, Navigation System
Transmission: Automatic Color:Silver Interior Color: Black Average Vehicle Review: (4.563 reviews)

2019 Chrysler 300 Limited

$22,998* 33K Miles


CarMax Kenosha Free shipping • WI to IL

Key Features
Leather Seats, Alpine Sound System, Rear View Camera, Navigation System, Front Seat Heaters, A/C Seat(s)
Location: CarMax Kenosha in Kenosha, Wisconsin 53142
Description: Used 2019 Chrysler 300 Limited for sale - $22,998, 32,729 miles with Leather Seats, Alpine Sound System, Rear View Camera, Navigation System, Front Seat Heaters, A/C Seat(s)
Transmission: Automatic Color:Gray Interior Color: Black Average Vehicle Review: (4 reviews)

2014 Chrysler 300 S

$20,998* 21K Miles


CarMax Kenosha Free shipping • WI to IL

Key Features
Leather Seats, Rear View Camera, Navigation System, Front Seat Heaters, Panoramic Sunroof, Satellite Radio Ready
Location: CarMax Kenosha in Kenosha, Wisconsin 53142
Description: Used 2014 Chrysler 300 S for sale - $20,998, 20,475 miles with Leather Seats, Rear View Camera, Navigation System, Front Seat Heaters, Panoramic Sunroof, Satellite Radio Ready
Transmission: Automatic Color:Red Interior Color: Black Average Vehicle Review: (4.539 reviews)

2017 Chrysler 300 S

$21,998* 44K Miles


CarMax Kenosha Free shipping • WI to IL

Key Features
4WD/AWD, Leather Seats, Rear View Camera, Navigation System, Front Seat Heaters, Satellite Radio Ready
Location: CarMax Kenosha in Kenosha, Wisconsin 53142
Description: Used 2017 Chrysler 300 S for sale - $21,998, 43,822 miles with 4WD/AWD, Leather Seats, Rear View Camera, Navigation System, Front Seat Heaters, Satellite Radio Ready
Transmission: Automatic Color:Blue Interior Color: Black Average Vehicle Review: (5 reviews)

2018 Chrysler 300 S

$22,998* 23K Miles


CarMax Milwaukee Free shipping • WI to IL

Key Features
4WD/AWD, Leather Seats, Rear View Camera, Front Seat Heaters, Satellite Radio Ready, Auxiliary Audio Input
Location: CarMax Milwaukee in Milwaukee, Wisconsin 53224
Description: Used 2018 Chrysler 300 S for sale - $22,998, 22,234 miles with 4WD/AWD, Leather Seats, Rear View Camera, Front Seat Heaters, Satellite Radio Ready, Auxiliary Audio Input
Transmission: Automatic Color:Gray Interior Color: Black Average Vehicle Review: (5 reviews)

2016 Chrysler 300 S

$19,998* 35K Miles


CarMax Fort Wayne Free shipping • IN to IL

Key Features
4WD/AWD, Leather Seats, Rear View Camera, Navigation System, Front Seat Heaters, Satellite Radio Ready
Location: CarMax Fort Wayne in Fort Wayne, Indiana 46805
Description: Used 2016 Chrysler 300 S for sale - $19,998, 34,381 miles with 4WD/AWD, Leather Seats, Rear View Camera, Navigation System, Front Seat Heaters, Satellite Radio Ready
Transmission: Automatic Color:Black Interior Color: Black Average Vehicle Review: (4.563 reviews)

2017 Chrysler 300 Limited

$19,998* 39K Miles


CarMax Fort Wayne Free shipping • IN to IL

Key Features
Premium Package, 4WD/AWD, Leather Seats, Parking Sensors, Rear View Camera, Navigation System
Location: CarMax Fort Wayne in Fort Wayne, Indiana 46805
Description: Used 2017 Chrysler 300 Limited for sale - $19,998, 38,455 miles with Premium Package, 4WD/AWD, Leather Seats, Parking Sensors, Rear View Camera, Navigation System
Transmission: Automatic Color:Gray Interior Color: Black Average Vehicle Review: (5 reviews)

2016 Chrysler 300 S Alloy Edition

$19,998* 58K Miles


CarMax Indianapolis Free shipping • IN to IL

Key Features
4WD/AWD, Leather Seats, Parking Sensors, Rear View Camera, Navigation System, Front Seat Heaters
Location: CarMax Indianapolis in Indianapolis, Indiana 46280
Description: Used 2016 Chrysler 300 S Alloy Edition for sale - $19,998, 57,736 miles with 4WD/AWD, Leather Seats, Parking Sensors, Rear View Camera, Navigation System, Front Seat Heaters
Transmission: Automatic Color:Black Interior Color: Black Average Vehicle Review: (4.563 reviews)
New Arrival

2016 Chrysler 300 S

$20,998* 52K Miles


CarMax Indianapolis Free shipping • IN to IL

Key Features
Premium Package, 4WD/AWD, Leather Seats, Parking Sensors, Rear View Camera, Navigation System
Location: CarMax Indianapolis in Indianapolis, Indiana 46280
Description: Used 2016 Chrysler 300 S for sale - $20,998, 51,322 miles with Premium Package, 4WD/AWD, Leather Seats, Parking Sensors, Rear View Camera, Navigation System
Transmission: Automatic Color:Gray Interior Color: Black Average Vehicle Review: (4.563 reviews)

2016 Chrysler 300 Anniversary Edition

$20,998* 26K Miles


CarMax Indianapolis Free shipping • IN to IL

Key Features
4WD/AWD, Leather Seats, Rear View Camera, Navigation System, Front Seat Heaters, Panoramic Sunroof
Location: CarMax Indianapolis in Indianapolis, Indiana 46280
Description: Used 2016 Chrysler 300 Anniversary Edition for sale - $20,998, 25,372 miles with 4WD/AWD, Leather Seats, Rear View Camera, Navigation System, Front Seat Heaters, Panoramic Sunroof
Transmission: Automatic Color:White Interior Color: Black Average Vehicle Review: (4.563 reviews)

Reviews for Chrysler 300

Overall Rating

4.6 out of 5(363 reviews)

300C AWD

After owning over 35 cars in my lifetime, this is "the best" all season vehicle I have ever owned. With the Hemi engine (which I had tweaked w/434bhp) and AWD it can be driven in any kind of weather but like a sports car or Bentley. Standard with every option you can think of it's a fantastic purchase. I would take this car over any SUV which I have owned many. I get nearly 30 mpg on trips w/four cylinder deactivation, fantastic!!

- Paul Stolarski, 2014 Chrysler 300

This car was actually mine

This red car pictured, was actually my car. I loved this car, it was the 2nd Chrysler 300 limited I had. Actually when we took long road trips, it would get 30 MPG. I originally bought it, because it has the largest back seat of any car, being a realtor, I wanted my clients to be comfortable. Lot's of room , great to drive and just an all around great car. Only reason I sold it was to get a mini van for my 3 grandchildren's car seats. Highly recommend the 300.

- Chris S., 2011 Chrysler 300

CHRYSLER 300

THE 2005 CHRYSLER 300 IS CERTAINLY A TOP OF THE LINE VEHICLE. IT WAS TRULY DESIGNED FOR PEOPLE OF ALL SHAPES, AND LENGTHS, AND THE SPACIOUS STYLE ACCOMODATES THE NEEDS FOR A FAMILY OF FOUR. ALTHOUGH, THE 2005 IS WONDERFUL, THE DESIGNER SPECIALIST OF THE 2012 CHRYSLER 300 GAVE US SOMETHING TO LOOK FORWARD TO. WE WOULD DEFINATELY PURCHASE ANOTHER CHRYSLER WITH THE 2012 IN MIND. IT IS BY FAR THE MOST PHENOMINAL VEHICLE ON THE MARKET. GO...............CHRYSLER.

- PASSION, 2005 Chrysler 300

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