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Used 2021 Chrysler 300 for Sale in Chicago, IL

300s for Sale at Dealers

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2023 Chrysler 300 300C RWD photo
Price Drop
2023 Chrysler 300 300C RWD • Libertyville, IL
White • 6.4L V8 Engine
$54,683 • 15k miles
•••

#26 2019-2023 Chrysler 300

CoPilot AI: It’s a “F” Buy

  • $309 Price Drop
  • Motivation to Negotiate - Increasing
  • Very Low Mileage
More details
2020 Chrysler 300 300S RWD photo
25
Price Drop
2020 Chrysler 300 300S RWD • Milwaukee, WI
Black • 3.6L V6 Engine
$21,675 • 74.7k miles
•••

#25 2019-2023 Chrysler 300

CoPilot AI: It’s a “F” Buy

  • $202 Price Drop
  • Includes $491 Premium Upgrades
  • CARFAX: One Owner
More details
2023 Chrysler 300 Touring L AWD photo
1
Price Drop
2023 Chrysler 300 Touring L AWD • Milwaukee, WI
Black • 3.6L V6 Engine
$31,147 • 36.3k miles
•••

#1 2019-2023 Chrysler 300

CoPilot AI: It’s a “B+” Buy

  • $1,428 Price Drop
  • Great Price - $4,234 Below Market
  • Includes $5,040 Premium Upgrades
More details
2022 Chrysler 300 Touring RWD photo
19
2022 Chrysler 300 Touring RWD • North Aurora, IL
White • 3.6L V6 Engine
$27,950 • 32.6k miles
•••

#19 2019-2023 Chrysler 300

CoPilot AI: It’s a “D” Buy

  • Includes $973 Premium Upgrades
  • CARFAX: One Owner
  • Very Low Mileage
More details
2020 Chrysler 300 300S RWD photo
11
Price Drop
2020 Chrysler 300 300S RWD • Crestwood, IL
Black • 3.6L V6 Engine
$17,495 • 84.6k miles
•••

#11 2019-2023 Chrysler 300

CoPilot AI: It’s a “B-” Buy

  • $500 Price Drop
  • Good Price - $613 Below Market
  • Motivation to Negotiate - Very High
More details
2023 Chrysler 300 Touring L AWD photo
18
2023 Chrysler 300 Touring L AWD • Schererville, IN
White • 3.6L V6 Engine
$29,995 • 17.7k miles
•••

#18 2019-2023 Chrysler 300

CoPilot AI: It’s a “D+” Buy

  • Very Low Mileage
  • Dealer Rating - 4.9 stars
More details
2023 Chrysler 300 Touring L RWD photo
6
Price Drop
2023 Chrysler 300 Touring L RWD • Crystal Lake, IL
White • 3.6L V6 Engine
$29,208 • 47.4k miles
•••

#6 2019-2023 Chrysler 300

CoPilot AI: It’s a “B+” Buy

  • $483 Price Drop
  • Great Price - $2,389 Below Market
  • Includes $4,687 Premium Upgrades
More details
2019 Chrysler 300 300S AWD photo
22
2019 Chrysler 300 300S AWD • Burbank, IL
Gray • 3.6L V6 Engine
$19,995 • 75.4k miles
•••

#22 2019-2023 Chrysler 300

CoPilot AI: It’s a “D-” Buy

  • Motivation to Negotiate - Increasing
  • Below Average Mileage
  • Dealer Rating - 4.3 stars
More details
2023 Chrysler 300 300C RWD photo
Price Drop
2023 Chrysler 300 300C RWD • St. Charles, IL
Red • 6.4L V8 Engine
$53,995 • 21.5k miles
•••

#27 2019-2023 Chrysler 300

CoPilot AI: It’s a “F” Buy

  • $807 Price Drop
  • Very Low Mileage
  • Dealer Rating - 4.5 stars
More details
2023 Chrysler 300 Touring L RWD photo
2
Price Drop
2023 Chrysler 300 Touring L RWD • St. Charles, IL
Black • 3.6L V6 Engine
$29,209 • 41.2k miles
•••

#2 2019-2023 Chrysler 300

CoPilot AI: It’s a “B+” Buy

  • $200 Price Drop
  • Great Price - $3,603 Below Market
  • Includes $4,868 Premium Upgrades
More details
2020 Chrysler 300 Limited AWD photo
10
Price Drop
2020 Chrysler 300 Limited AWD • Mokena, IL
Black • 3.6L V6 Engine
$16,998 • 88.1k miles
•••

#10 2019-2023 Chrysler 300

CoPilot AI: It’s a “B” Buy

  • $500 Price Drop
  • Fair Price - $43 Above Market
  • Includes $1,163 Premium Upgrades
More details
2022 Chrysler 300 300S RWD photo
20
2022 Chrysler 300 300S RWD • Elgin, IL
White • 5.7L V8 Engine
$32,360 • 65.5k miles
•••

#20 2019-2023 Chrysler 300

CoPilot AI: It’s a “D” Buy

  • Includes $1,699 Premium Upgrades
  • Dealer Rating - 4.4 stars
More details
2022 Chrysler 300 Touring AWD photo
12
2022 Chrysler 300 Touring AWD • Crystal Lake, IL
Gray • 3.6L V6 Engine
$25,495 • 61.5k miles
•••

#12 2019-2023 Chrysler 300

CoPilot AI: It’s a “C+” Buy

  • Fair Price - $326 Below Market
  • CARFAX: One Owner
  • Average Mileage
More details
2019 Chrysler 300 Touring AWD photo
23
2019 Chrysler 300 Touring AWD • Elkhorn, WI
Red • 3.6L V6 Engine
$14,999 • 117.4k miles
•••

#23 2019-2023 Chrysler 300

CoPilot AI: It’s a “D-” Buy

  • Includes $489 Premium Upgrades
  • CARFAX: One Owner
More details
2023 Chrysler 300 Touring RWD photo
24
2023 Chrysler 300 Touring RWD • Benton Harbor, MI
Black • 3.6L V6 Engine
$33,900 • 12.6k miles
•••

#24 2019-2023 Chrysler 300

CoPilot AI: It’s a “D-” Buy

  • Includes $1,282 Premium Upgrades
  • Motivation to Negotiate - Very High
  • Very Low Mileage
More details
2019 Chrysler 300 Limited RWD photo
15
Price Drop
2019 Chrysler 300 Limited RWD • Oswego, IL
Gray • 3.6L V6 Engine
$11,677 • 131k miles
•••

#15 2019-2023 Chrysler 300

CoPilot AI: It’s a “C+” Buy

  • $520 Price Drop
  • Fair Price - $155 Below Market
  • CARFAX: One Owner
More details
2023 Chrysler 300 Touring L RWD photo
5
Price Drop
2023 Chrysler 300 Touring L RWD • St. Charles, IL
Black • 3.6L V6 Engine
$28,995 • 47.3k miles
•••

#5 2019-2023 Chrysler 300

CoPilot AI: It’s a “B+” Buy

  • $309 Price Drop
  • Great Price - $2,608 Below Market
  • Includes $4,688 Premium Upgrades
More details
2023 Chrysler 300 300S RWD photo
4
Price Drop
2023 Chrysler 300 300S RWD • Schaumburg, IL
White • 3.6L V6 Engine
$26,500 • 37.1k miles
•••

#4 2019-2023 Chrysler 300

CoPilot AI: It’s a “B+” Buy

  • $481 Price Drop
  • Great Price - $3,099 Below Market
  • Includes $1,368 Premium Upgrades
More details
2023 Chrysler 300 Touring L RWD photo
3
Price Drop
2023 Chrysler 300 Touring L RWD • St. Charles, IL
Black • 3.6L V6 Engine
$29,690 • 40k miles
•••

#3 2019-2023 Chrysler 300

CoPilot AI: It’s a “B+” Buy

  • $5 Price Drop
  • Great Price - $3,362 Below Market
  • Includes $4,903 Premium Upgrades
More details
2019 Chrysler 300 Limited RWD photo
9
Price Drop
2019 Chrysler 300 Limited RWD • Waukegan, IL
Red • 3.6L V6 Engine
$13,799 • 116.1k miles
•••

#9 2019-2023 Chrysler 300

CoPilot AI: It’s a “B” Buy

  • $200 Price Drop
  • Fair Price - $271 Below Market
  • Includes $987 Premium Upgrades
More details
2021 Chrysler 300 Touring RWD photo
14
Price Drop
2021 Chrysler 300 Touring RWD • Berwyn, IL
Silver • 3.6L V6 Engine
$14,988 • 121.9k miles
•••

#14 2019-2023 Chrysler 300

CoPilot AI: It’s a “C+” Buy

  • $500 Price Drop
  • Fair Price - $281 Below Market
  • Includes $673 Premium Upgrades
More details
2020 Chrysler 300 Touring RWD photo
16
Price Drop
2020 Chrysler 300 Touring RWD • Milwaukee, WI
Blue • 3.6L V6 Engine
$17,407 • 88.7k miles
•••

#16 2019-2023 Chrysler 300

CoPilot AI: It’s a “C+” Buy

  • $127 Price Drop
  • Fair Price - $134 Above Market
  • CARFAX: One Owner
More details
2022 Chrysler 300 300S RWD photo
13
Price Drop
2022 Chrysler 300 300S RWD • Willowbrook, IL
White • 3.6L V6 Engine
$24,775 • 53.2k miles
•••

#13 2019-2023 Chrysler 300

CoPilot AI: It’s a “C+” Buy

  • $125 Price Drop
  • Fair Price - $284 Below Market
  • Below Average Mileage
More details
2021 Chrysler 300 300S RWD photo
8
2021 Chrysler 300 300S RWD • Barrington, IL
Gray • 3.6L V6 Engine
$21,501 • 76.8k miles
•••

#8 2019-2023 Chrysler 300

CoPilot AI: It’s a “B” Buy

  • Fair Price - $445 Below Market
  • Includes $1,533 Premium Upgrades
  • Average Mileage
More details
2019 Chrysler 300 Touring RWD photo
21
2019 Chrysler 300 Touring RWD • Dyer, IN
Gray • 3.6L V6 Engine
$16,900 • 87.9k miles
•••

#21 2019-2023 Chrysler 300

CoPilot AI: It’s a “D-” Buy

  • Includes $632 Premium Upgrades
  • CARFAX: One Owner
  • Below Average Mileage
More details
1-25 of 47 results
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2021 Chrysler 300

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