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Used 2021 Chrysler 300 for Sale in Chicago, IL

300s for Sale at Dealers

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2020 Chrysler 300 300S RWD photo
5
2020 Chrysler 300 300S RWD • Aurora, IL
Silver • 3.6L V6 Engine
$17,995 • 84.3k miles
•••

#5 2019-2023 Chrysler 300

CoPilot AI: It’s a “B+” Buy

  • Great Price - $1,271 Below Market
  • Average Mileage
  • Dealer Rating - 4.4 stars
More details
2022 Chrysler 300 Touring L AWD photo
8
2022 Chrysler 300 Touring L AWD • Oak Lawn, IL
Red • 3.6L V6 Engine
$27,998 • 27.2k miles • Certified
•••

#8 2019-2023 Chrysler 300

CoPilot AI: It’s a “B+” Buy

  • Fair Price - $629 Above Market
  • Includes $2,289 Premium Upgrades
  • CARFAX: One Owner
More details
2023 Chrysler 300 300C RWD photo
20
2023 Chrysler 300 300C RWD • St. Charles, IL
Black • 6.4L V8 Engine
$48,688 • 21.9k miles
•••

#20 2019-2023 Chrysler 300

CoPilot AI: It’s a “D+” Buy

  • Very Low Mileage
  • Dealer Rating - 4.5 stars
More details
2019 Chrysler 300 300S AWD photo
4
2019 Chrysler 300 300S AWD • Chicago, IL
Black • 3.6L V6 Engine
$15,999 • 80.6k miles
•••

#4 2019-2023 Chrysler 300

CoPilot AI: It’s a “B+” Buy

  • Great Price - $1,426 Below Market
  • Motivation to Negotiate - Increasing
  • Below Average Mileage
More details
2022 Chrysler 300 Touring AWD photo
2
Price Drop
2022 Chrysler 300 Touring AWD • Naperville, IL
3.6L V6 Engine
$19,477 • 97.5k miles
•••

#2 2019-2023 Chrysler 300

CoPilot AI: It’s a “B+” Buy

  • $200 Price Drop
  • Great Price - $1,964 Below Market
  • Includes $816 Premium Upgrades
More details
2019 Chrysler 300 Touring RWD photo
18
Price Drop
2019 Chrysler 300 Touring RWD • Beloit, WI
White • 3.6L V6 Engine
$16,961 • 77k miles
•••

#18 2019-2023 Chrysler 300

CoPilot AI: It’s a “C” Buy

  • $313 Price Drop
  • Includes $657 Premium Upgrades
  • Below Average Mileage
More details
2023 Chrysler 300 300S RWD photo
11
Price Drop
2023 Chrysler 300 300S RWD • Chicago, IL
Silver • 3.6L V6 Engine
$25,695 • 44.3k miles
•••

#11 2019-2023 Chrysler 300

CoPilot AI: It’s a “B-” Buy

  • $900 Price Drop
  • Good Price - $921 Below Market
  • CARFAX: One Owner
More details
2020 Chrysler 300 Limited RWD photo
7
2020 Chrysler 300 Limited RWD • Peru, IL
Red • 3.6L V6 Engine
$19,995 • 67.7k miles
•••

#7 2019-2023 Chrysler 300

CoPilot AI: It’s a “B+” Buy

  • Fair Price - $295 Below Market
  • Includes $1,408 Premium Upgrades
  • Below Average Mileage
More details
2023 Chrysler 300 Touring AWD photo
2023 Chrysler 300 Touring AWD • Lincolnwood, IL
3.6L V6 Engine
$25,605 • 55.2k miles
•••
More details
2023 Chrysler 300 Touring RWD photo
25
Price Drop
2023 Chrysler 300 Touring RWD • Homewood, IL
White • 3.6L V6 Engine
$25,495 • 24.4k miles
•••

#25 2019-2023 Chrysler 300

CoPilot AI: It’s a “D-” Buy

  • $495 Price Drop
  • Includes $1,202 Premium Upgrades
  • Motivation to Negotiate - High
More details
2019 Chrysler 300 300S AWD photo
2019 Chrysler 300 300S AWD • Benton Harbor, MI
Gray • 3.6L V6 Engine
$17,500 • 99.7k miles
•••

#28 2019-2023 Chrysler 300

CoPilot AI: It’s a “F” Buy

  • Motivation to Negotiate - Increasing
  • Average Mileage
  • Dealer Rating - 4.6 stars
More details
2023 Chrysler 300 300S RWD photo
14
Price Drop
2023 Chrysler 300 300S RWD • Lombard, IL
Silver • 3.6L V6 Engine
$24,860 • 64.6k miles
•••

#14 2019-2023 Chrysler 300

CoPilot AI: It’s a “C+” Buy

  • $1,120 Price Drop
  • Fair Price - $463 Below Market
  • CARFAX: One Owner
More details
2023 Chrysler 300 300S RWD photo
17
Price Drop
2023 Chrysler 300 300S RWD • North Riverside, IL
Gray • 3.6L V6 Engine
$24,594 • 76.5k miles
•••

#17 2019-2023 Chrysler 300

CoPilot AI: It’s a “C+” Buy

  • $300 Price Drop
  • Fair Price - $389 Above Market
  • CARFAX: One Owner
More details
2019 Chrysler 300 Touring AWD photo
24
2019 Chrysler 300 Touring AWD • Tinley Park, IL
Black • 3.6L V6 Engine
$19,998 • 85.4k miles
•••

#24 2019-2023 Chrysler 300

CoPilot AI: It’s a “D-” Buy

  • Includes $624 Premium Upgrades
  • CARFAX: One Owner
  • Below Average Mileage
More details
2019 Chrysler 300 300S RWD photo
13
2019 Chrysler 300 300S RWD • Elmhurst, IL
Gray • 3.6L V6 Engine
$19,920 • 61k miles
•••

#13 2019-2023 Chrysler 300

CoPilot AI: It’s a “B-” Buy

  • Fair Price - $13 Above Market
  • CARFAX: One Owner
  • Motivation to Negotiate - Very High
More details
2021 Chrysler 300 Touring RWD photo
12
2021 Chrysler 300 Touring RWD • Berwyn, IL
Silver • 3.6L V6 Engine
$15,488 • 121.9k miles
•••

#12 2019-2023 Chrysler 300

CoPilot AI: It’s a “B-” Buy

  • Good Price - $667 Below Market
  • Includes $712 Premium Upgrades
  • Motivation to Negotiate - Very High
More details
2021 Chrysler 300 Touring L AWD photo
22
2021 Chrysler 300 Touring L AWD • Aurora, IL
Brown • 3.6L V6 Engine
$21,995 • 65.7k miles
•••

#22 2019-2023 Chrysler 300

CoPilot AI: It’s a “D” Buy

  • Includes $2,042 Premium Upgrades
  • Below Average Mileage
  • Dealer Rating - 4.4 stars
More details
2020 Chrysler 300 Limited AWD photo
23
Price Drop
2020 Chrysler 300 Limited AWD • Mokena, IL
Black • 3.6L V6 Engine
$19,498 • 88.1k miles
•••

#23 2019-2023 Chrysler 300

CoPilot AI: It’s a “D” Buy

  • $1,000 Price Drop
  • Includes $1,126 Premium Upgrades
  • Motivation to Negotiate - High
More details
2022 Chrysler 300 Touring RWD photo
19
Price Drop
2022 Chrysler 300 Touring RWD • Orland Park, IL
Silver • 3.6L V6 Engine
$23,485 • 38.6k miles
•••

#19 2019-2023 Chrysler 300

CoPilot AI: It’s a “C” Buy

  • $301 Price Drop
  • Includes $969 Premium Upgrades
  • CARFAX: One Owner
More details
2023 Chrysler 300 Touring RWD photo
1
2023 Chrysler 300 Touring RWD • Orland Park, IL
White • 3.6L V6 Engine
$23,999 • 52k miles
•••

#1 2019-2023 Chrysler 300

CoPilot AI: It’s a “B+” Buy

  • Great Price - $2,886 Below Market
  • Includes $1,025 Premium Upgrades
  • CARFAX: One Owner
More details
2019 Chrysler 300 Touring L RWD photo
21
2019 Chrysler 300 Touring L RWD • Crestwood, IL
Gray • 3.6L V6 Engine
$11,900 • 151.5k miles
•••

#21 2019-2023 Chrysler 300

CoPilot AI: It’s a “D” Buy

  • Includes $1,316 Premium Upgrades
  • CARFAX: One Owner
  • Motivation to Negotiate - Increasing
More details
2023 Chrysler 300 300S RWD photo
9
2023 Chrysler 300 300S RWD • Lansing, IL
3.6L V6 Engine
$26,900 • 25.9k miles
•••

#9 2019-2023 Chrysler 300

CoPilot AI: It’s a “B” Buy

  • Good Price - $1,207 Below Market
  • CARFAX: One Owner
  • Very Low Mileage
More details
2023 Chrysler 300 300S RWD photo
15
Price Drop
2023 Chrysler 300 300S RWD • Plainfield, IL
White • 3.6L V6 Engine
$26,227 • 42.1k miles
•••

#15 2019-2023 Chrysler 300

CoPilot AI: It’s a “C+” Buy

  • $952 Price Drop
  • Fair Price - $23 Below Market
  • CARFAX: One Owner
More details
2023 Chrysler 300 Touring L RWD photo
Price Drop
2023 Chrysler 300 Touring L RWD • Highland, IN
Gray • 3.6L V6 Engine
$28,491 • 8.7k miles • Certified
•••

#26 2019-2023 Chrysler 300

CoPilot AI: It’s a “D-” Buy

  • $464 Price Drop
  • CARFAX: One Owner
  • Very Low Mileage
More details
2019 Chrysler 300 Limited RWD photo
16
Price Drop
2019 Chrysler 300 Limited RWD • Oswego, IL
Gray • 3.6L V6 Engine
$12,197 • 131k miles
•••

#16 2019-2023 Chrysler 300

CoPilot AI: It’s a “C+” Buy

  • $800 Price Drop
  • Fair Price - $301 Above Market
  • CARFAX: One Owner
More details
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2021 Chrysler 300

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