CoPilot AI-Assisted Car Shopping

 New Search
 Save
 Sort
 Share

Used 2020 Jeep Cherokee for Sale in Madison, WI

Cherokees for Sale at Dealers

Filters
Price
Year
Mileage
Trim
2019 Jeep Cherokee Latitude Plus 4WD photo
2019 Jeep Cherokee Latitude Plus 4WD • Madison, WI
Gray • 3.2L V6 Engine
$17,389 • 78k miles
•••

Not Ranked

CoPilot AI: It’s a “B” Buy

  • Includes $2,109 Premium Upgrades
  • CARFAX: One Owner
  • Below Average Mileage
More details
2019 Jeep Cherokee Limited 4WD photo
Price Drop
New Find
2019 Jeep Cherokee Limited 4WD • Madison, WI
Gray • 3.2L V6 Engine
$18,209 • 61.5k miles
•••

Not Ranked

CoPilot AI: It’s a “B+” Buy

  • $218 Price Drop
  • Good Price - $1,033 Below Market
  • Includes $1,920 Premium Upgrades
More details
2019 Jeep Cherokee Limited 4WD photo
2019 Jeep Cherokee Limited 4WD • Madison, WI
Blue • 3.2L V6 Engine
$17,394 • 80.9k miles
•••

Not Ranked

CoPilot AI: It’s a “B+” Buy

  • Fair Price - $169 Below Market
  • Includes $1,583 Premium Upgrades
  • Below Average Mileage
More details
2021 Jeep Cherokee Altitude 4WD photo
New Find
2021 Jeep Cherokee Altitude 4WD • Madison, WI
Black • 2.4L I4 Engine
$17,496 • 94k miles
•••

Not Ranked

CoPilot AI: It’s a “C-” Buy

  • Includes $1,482 Premium Upgrades
  • CARFAX: One Owner
  • Dealer Rating - 4.4 stars
More details
2020 Jeep Cherokee Latitude Plus 4WD photo
2020 Jeep Cherokee Latitude Plus 4WD • Madison, WI
White • 2.0L I4 Engine
$12,999 • 61k miles
•••

Not Ranked

CoPilot AI: It’s an “A+” Buy

  • Great Price - $5,802 Below Market
  • Includes $1,237 Premium Upgrades
  • Motivation to Negotiate - Increasing
More details
2019 Jeep Cherokee Latitude Plus 4WD photo
2019 Jeep Cherokee Latitude Plus 4WD • Madison, WI
Gray • 2.4L I4 Engine
$13,390 • 107.5k miles
•••

Not Ranked

CoPilot AI: It’s a “C” Buy

  • Includes $370 Premium Upgrades
More details
2021 Jeep Cherokee Latitude Lux 4WD photo
Price Drop
2021 Jeep Cherokee Latitude Lux 4WD • Madison, WI
Black • 3.2L V6 Engine
$18,099 • 70.5k miles
•••

Not Ranked

CoPilot AI: It’s a “B+” Buy

  • $200 Price Drop
  • Good Price - $1,027 Below Market
  • Includes $1,063 Premium Upgrades
More details
2019 Jeep Cherokee Latitude 4WD photo
Price Drop
2019 Jeep Cherokee Latitude 4WD • Madison, WI
Tan • 2.4L I4 Engine
$13,981 • 85.5k miles
•••

Not Ranked

CoPilot AI: It’s a “D+” Buy

  • $297 Price Drop
  • Includes $770 Premium Upgrades
  • Motivation to Negotiate - Increasing
More details
2019 Jeep Cherokee Latitude Plus FWD photo
2019 Jeep Cherokee Latitude Plus FWD • Stoughton, WI
Gray • 2.4L I4 Engine
$13,436 • 82.8k miles
•••

Not Ranked

CoPilot AI: It’s a “B” Buy

  • Fair Price - $49 Below Market
  • Includes $435 Premium Upgrades
  • Motivation to Negotiate - Increasing
More details
2019 Jeep Cherokee Latitude Plus FWD photo
Price Drop
2019 Jeep Cherokee Latitude Plus FWD • Stoughton, WI
Black • 2.0L I4 Engine
$14,041 • 84.3k miles
•••

Not Ranked

CoPilot AI: It’s an “A+” Buy

  • $958 Price Drop
  • Great Price - $1,613 Below Market
  • Includes $1,994 Premium Upgrades
More details
2019 Jeep Cherokee Limited FWD photo
Price Drop
2019 Jeep Cherokee Limited FWD • Stoughton, WI
Gray • 2.4L I4 Engine
$11,998 • 119.4k miles
•••

Not Ranked

CoPilot AI: It’s an “A-” Buy

  • $451 Price Drop
  • Good Price - $583 Below Market
  • Includes $890 Premium Upgrades
More details
2019 Jeep Cherokee Trailhawk Elite 4WD photo
2019 Jeep Cherokee Trailhawk Elite 4WD • Stoughton, WI
White • 3.2L V6 Engine
$17,286 • 89.6k miles
•••

Not Ranked

CoPilot AI: It’s a “B+” Buy

  • Fair Price - $421 Above Market
  • Includes $2,386 Premium Upgrades
  • Motivation to Negotiate - High
More details
2020 Jeep Cherokee Limited 4WD photo
New Find
2020 Jeep Cherokee Limited 4WD • Mt Horeb, WI
Red • 3.2L V6 Engine
$18,986 • 52.7k miles
•••

Not Ranked

CoPilot AI: It’s an “A” Buy

  • Good Price - $1,119 Below Market
  • Includes $1,221 Premium Upgrades
  • CARFAX: One Owner
More details
2021 Jeep Cherokee Latitude Lux 4WD photo
Price Drop
2021 Jeep Cherokee Latitude Lux 4WD • Mt Horeb, WI
White • 3.2L V6 Engine
$14,909 • 95.7k miles
•••

Not Ranked

CoPilot AI: It’s a “B+” Buy

  • $1,082 Price Drop
  • Fair Price - $351 Below Market
  • Includes $534 Premium Upgrades
More details
2019 Jeep Cherokee Trailhawk Elite 4WD photo
Price Drop
2019 Jeep Cherokee Trailhawk Elite 4WD • Sauk City, WI
Gray • 3.2L V6 Engine
$16,249 • 95.6k miles
•••

Not Ranked

CoPilot AI: It’s a “B-” Buy

  • $247 Price Drop
  • Includes $2,180 Premium Upgrades
  • Motivation to Negotiate - Increasing
More details
2021 Jeep Cherokee Altitude 4WD photo
Price Drop
2021 Jeep Cherokee Altitude 4WD • Sauk City, WI
Gray • 2.4L I4 Engine
$16,849 • 92.3k miles • Certified
•••

Not Ranked

CoPilot AI: It’s a “D+” Buy

  • $150 Price Drop
  • Includes $536 Premium Upgrades
  • CARFAX: One Owner
More details
2021 Jeep Cherokee Latitude Lux 4WD photo
New Find
2021 Jeep Cherokee Latitude Lux 4WD • Jefferson, WI
Black • 3.2L V6 Engine
$16,597 • 92.7k miles
•••

Not Ranked

CoPilot AI: It’s a “B+” Buy

  • Fair Price - $384 Above Market
  • Includes $548 Premium Upgrades
  • Dealer Rating - 4.5 stars
More details
2021 Jeep Cherokee Trailhawk 4WD photo
2021 Jeep Cherokee Trailhawk 4WD • Jefferson, WI
Silver • 3.2L V6 Engine
$22,494 • 44.8k miles
•••

Not Ranked

CoPilot AI: It’s an “A-” Buy

  • Fair Price - $557 Above Market
  • Includes $956 Premium Upgrades
  • CARFAX: One Owner
More details
2021 Jeep Cherokee Limited 4WD photo
New Find
2021 Jeep Cherokee Limited 4WD • Janesville, WI
Silver • 3.2L V6 Engine
$17,494 • 113.8k miles
•••

Not Ranked

CoPilot AI: It’s a “D” Buy

  • Dealer Rating - 4.5 stars
More details
2019 Jeep Cherokee Limited 4WD photo
New Find
2019 Jeep Cherokee Limited 4WD • Janesville, WI
Black • 3.2L V6 Engine
$16,120 • 70.1k miles
•••

Not Ranked

CoPilot AI: It’s an “A+” Buy

  • Great Price - $2,531 Below Market
  • Includes $1,849 Premium Upgrades
  • CARFAX: One Owner
More details
2020 Jeep Cherokee Limited 4WD photo
New Find
2020 Jeep Cherokee Limited 4WD • Janesville, WI
Black • 3.2L V6 Engine
$16,624 • 77.9k miles
•••

Not Ranked

CoPilot AI: It’s a “B” Buy

  • Fair Price - $360 Below Market
  • Average Mileage
  • Dealer Rating - 4.3 stars
More details
2019 Jeep Cherokee Limited FWD photo
New Find
2019 Jeep Cherokee Limited FWD • Milton, WI
Gray • 2.4L I4 Engine
$14,468 • 92.3k miles
•••

Not Ranked

CoPilot AI: It’s a “D” Buy

  • Average Mileage
  • Dealer Rating - 4.9 stars
More details
2019 Jeep Cherokee High Altitude 4WD photo
Price Drop
New Find
2019 Jeep Cherokee High Altitude 4WD • Janesville, WI
Black • 3.2L V6 Engine
$18,765 • 62.7k miles
•••

Not Ranked

CoPilot AI: It’s an “A+” Buy

  • $234 Price Drop
  • Good Price - $755 Below Market
  • Includes $1,860 Premium Upgrades
More details
2021 Jeep Cherokee Trailhawk 4WD photo
New Find
2021 Jeep Cherokee Trailhawk 4WD • Janesville, WI
Red • 3.2L V6 Engine
$22,881 • 53.8k miles
•••

Not Ranked

CoPilot AI: It’s a “B” Buy

  • Includes $1,376 Premium Upgrades
  • Very Low Mileage
  • Dealer Rating - 4.3 stars
More details
2020 Jeep Cherokee Limited 4WD photo
Price Drop
2020 Jeep Cherokee Limited 4WD • Baraboo, WI
2.0L I4 Engine
$21,435 • 92.3k miles
•••

Not Ranked

CoPilot AI: It’s a “D” Buy

  • $100 Price Drop
  • Includes $219 Premium Upgrades
  • Motivation to Negotiate - Increasing
More details
1-25 of 206 results

2020 Jeep Cherokee

Mid-size Crossover
Seats
5
Fuel Economy
22City MPG
31Hwy MPG
NHTSA Rating Summary
Copilot Rating
Dimensions
Most Popular Models like Cherokee
Jeep Cherokee near Madison, WI
Other Years
Research More Models
View more SUVs

© 2026 CoPilot. All Rights Reserved.