CoPilot AI-Assisted Car Shopping

 New Search
 Save
 Sort
 Share

Used 2020 Jeep Cherokee for Sale in Milwaukee, WI

Cherokees for Sale at Dealers

Filters
Price
Year
Mileage
Trim
2020 Jeep Cherokee Latitude Plus 4WD photo
Price Drop
2020 Jeep Cherokee Latitude Plus 4WD • Glendale, WI
3.2L V6 Engine
$21,433 • 20.1k miles • Certified
•••

Not Ranked

CoPilot AI: It’s an “A” Buy

  • $520 Price Drop
  • Fair Price - $284 Below Market
  • Includes $2,512 Premium Upgrades
More details
2020 Jeep Cherokee Latitude Plus 4WD photo
2020 Jeep Cherokee Latitude Plus 4WD • Milwaukee, WI
Black • 2.4L I4 Engine
$16,494 • 75.8k miles
•••

Not Ranked

CoPilot AI: It’s a “B” Buy

  • Fair Price - $101 Above Market
  • Includes $516 Premium Upgrades
  • Motivation to Negotiate - Increasing
More details
2019 Jeep Cherokee Limited 4WD photo
2019 Jeep Cherokee Limited 4WD • Milwaukee, WI
Gray • 3.2L V6 Engine
$18,999 • 82.6k miles
•••

Not Ranked

CoPilot AI: It’s a “C-” Buy

  • Includes $1,389 Premium Upgrades
  • Motivation to Negotiate - High
  • Below Average Mileage
More details
2019 Jeep Cherokee Latitude Plus 4WD photo
Price Drop
2019 Jeep Cherokee Latitude Plus 4WD • Milwaukee, WI
Gray • 2.4L I4 Engine
$8,999 • 171.1k miles
•••

Not Ranked

CoPilot AI: It’s a “C-” Buy

  • $1,000 Price Drop
  • Includes $249 Premium Upgrades
  • Motivation to Negotiate - Very High
More details
2019 Jeep Cherokee Limited 4WD photo
2019 Jeep Cherokee Limited 4WD • Milwaukee, WI
Black • 3.2L V6 Engine
$13,395 • 114.3k miles
•••

Not Ranked

CoPilot AI: It’s an “A-” Buy

  • Good Price - $809 Below Market
  • Includes $920 Premium Upgrades
  • Motivation to Negotiate - Increasing
More details
2020 Jeep Cherokee Limited 4WD photo
2020 Jeep Cherokee Limited 4WD • Milwaukee, WI
Red • 3.2L V6 Engine
$20,395 • 32.5k miles
•••

Not Ranked

CoPilot AI: It’s an “A-” Buy

  • Fair Price - $186 Below Market
  • Includes $1,012 Premium Upgrades
  • Motivation to Negotiate - Increasing
More details
2021 Jeep Cherokee Limited 4WD photo
Price Drop
2021 Jeep Cherokee Limited 4WD • Milwaukee, WI
Silver • 2.0L I4 Engine
$20,395 • 49.2k miles
•••

Not Ranked

CoPilot AI: It’s an “A” Buy

  • $1,000 Price Drop
  • Good Price - $739 Below Market
  • Includes $1,178 Premium Upgrades
More details
2021 Jeep Cherokee Trailhawk 4WD photo
Price Drop
2021 Jeep Cherokee Trailhawk 4WD • West Allis, WI
Red • 3.2L V6 Engine
$16,715 • 75.1k miles
•••

Not Ranked

CoPilot AI: It’s an “A” Buy

  • $591 Price Drop
  • Great Price - $1,734 Below Market
  • Includes $387 Premium Upgrades
More details
2019 Jeep Cherokee Overland 4WD photo
Price Drop
2019 Jeep Cherokee Overland 4WD • Milwaukee, WI
White • 2.0L I4 Engine
$13,995 • 104.5k miles
•••

Not Ranked

CoPilot AI: It’s an “A-” Buy

  • $1,000 Price Drop
  • Good Price - $804 Below Market
  • Includes $580 Premium Upgrades
More details
2020 Jeep Cherokee Limited 4WD photo
Price Drop
New Find
2020 Jeep Cherokee Limited 4WD • Milwaukee, WI
3.2L V6 Engine
$18,072 • 59.4k miles
•••

Not Ranked

CoPilot AI: It’s an “A+” Buy

  • $825 Price Drop
  • Great Price - $1,595 Below Market
  • Includes $1,263 Premium Upgrades
More details
2021 Jeep Cherokee 80th Anniversary 4WD photo
Price Drop
2021 Jeep Cherokee 80th Anniversary 4WD • Milwaukee, WI
Red • 3.2L V6 Engine
$21,171 • 20.6k miles
•••

Not Ranked

CoPilot AI: It’s an “A+” Buy

  • $541 Price Drop
  • Good Price - $1,077 Below Market
  • Includes $1,698 Premium Upgrades
More details
2021 Jeep Cherokee Trailhawk 4WD photo
Price Drop
New Find
2021 Jeep Cherokee Trailhawk 4WD • Greenfield, WI
White • 3.2L V6 Engine
$19,289 • 60.9k miles
•••

Not Ranked

CoPilot AI: It’s an “A” Buy

  • $310 Price Drop
  • Good Price - $852 Below Market
  • Includes $1,507 Premium Upgrades
More details
2021 Jeep Cherokee Trailhawk 4WD photo
Price Drop
2021 Jeep Cherokee Trailhawk 4WD • Milwaukee, WI
White • 3.2L V6 Engine
$20,479 • 40.7k miles
•••

Not Ranked

CoPilot AI: It’s an “A+” Buy

  • $704 Price Drop
  • Great Price - $4,720 Below Market
  • Includes $3,847 Premium Upgrades
More details
2021 Jeep Cherokee Altitude 4WD photo
2021 Jeep Cherokee Altitude 4WD • Milwaukee, WI
Gray • 2.4L I4 Engine
$21,379 • 58.8k miles
•••

Not Ranked

CoPilot AI: It’s a “C-” Buy

  • Includes $664 Premium Upgrades
  • CARFAX: One Owner
  • Below Average Mileage
More details
2019 Jeep Cherokee Latitude Plus 4WD photo
New Find
2019 Jeep Cherokee Latitude Plus 4WD • Milwaukee, WI
Gray • 3.2L V6 Engine
$17,257 • 72.7k miles
•••

Not Ranked

CoPilot AI: It’s a “C” Buy

  • Includes $1,674 Premium Upgrades
  • Below Average Mileage
  • Dealer Rating - 4.1 stars
More details
2020 Jeep Cherokee Latitude Plus 4WD photo
New Find
2020 Jeep Cherokee Latitude Plus 4WD • Milwaukee, WI
Red • 2.4L I4 Engine
$21,072 • 45.7k miles
•••

Not Ranked

CoPilot AI: It’s a “D+” Buy

  • Includes $581 Premium Upgrades
  • CARFAX: One Owner
  • Very Low Mileage
More details
2019 Jeep Cherokee Latitude FWD photo
Price Drop
2019 Jeep Cherokee Latitude FWD • Cudahy, WI
Black • 2.4L I4 Engine
$11,995 • 69.4k miles
•••

Not Ranked

CoPilot AI: It’s a “B+” Buy

  • $1,000 Price Drop
  • Great Price - $2,711 Below Market
  • Includes $933 Premium Upgrades
More details
2019 Jeep Cherokee Trailhawk 4WD photo
Price Drop
2019 Jeep Cherokee Trailhawk 4WD • Franklin, WI
Blue • 3.2L V6 Engine
$16,372 • 90k miles
•••

Not Ranked

CoPilot AI: It’s an “A-” Buy

  • $999 Price Drop
  • Fair Price - $438 Below Market
  • Includes $1,414 Premium Upgrades
More details
2019 Jeep Cherokee Limited 4WD photo
New Find
2019 Jeep Cherokee Limited 4WD • Lannon, WI
Black • 2.0L I4 Engine
$15,992 • 78.9k miles
•••

Not Ranked

CoPilot AI: It’s a “B+” Buy

  • Fair Price - $137 Above Market
  • Includes $223 Premium Upgrades
  • Below Average Mileage
More details
2019 Jeep Cherokee Trailhawk 4WD photo
New Find
2019 Jeep Cherokee Trailhawk 4WD • Waukesha, WI
Silver • 3.2L V6 Engine
$16,475 • 101.3k miles
•••

Not Ranked

CoPilot AI: It’s a “D” Buy

  • Average Mileage
More details
2021 Jeep Cherokee Latitude Lux 4WD photo
2021 Jeep Cherokee Latitude Lux 4WD • Waukesha, WI
Green • 3.2L V6 Engine
$19,075 • 73.9k miles
•••

Not Ranked

CoPilot AI: It’s a “D” Buy

  • Includes $446 Premium Upgrades
  • CARFAX: One Owner
  • Average Mileage
More details
2020 Jeep Cherokee Trailhawk 4WD photo
Price Drop
2020 Jeep Cherokee Trailhawk 4WD • Waukesha, WI
White • 3.2L V6 Engine
$17,685 • 64.1k miles
•••

Not Ranked

CoPilot AI: It’s a “B+” Buy

  • $188 Price Drop
  • Fair Price - $2 Above Market
  • Includes $490 Premium Upgrades
More details
2019 Jeep Cherokee Limited 4WD photo
New Find
2019 Jeep Cherokee Limited 4WD • Waukesha, WI
White • 3.2L V6 Engine
$17,739 • 76.9k miles
•••

Not Ranked

CoPilot AI: It’s an “A-” Buy

  • Fair Price - $444 Above Market
  • Includes $1,121 Premium Upgrades
  • Below Average Mileage
More details
2019 Jeep Cherokee Latitude Plus 4WD photo
New Find
2019 Jeep Cherokee Latitude Plus 4WD • Waukesha, WI
Gray • 2.4L I4 Engine
$18,075 • 27.8k miles
•••

Not Ranked

CoPilot AI: It’s a “C+” Buy

  • Very Low Mileage
  • Dealer Rating - 4.6 stars
More details
2019 Jeep Cherokee Latitude Plus FWD photo
2019 Jeep Cherokee Latitude Plus FWD • Racine, WI
Gray • 2.4L I4 Engine
$10,995 • 134.7k miles
•••

Not Ranked

CoPilot AI: It’s a “D” Buy

  • Motivation to Negotiate - Very High
More details
1-25 of 254 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 Milwaukee, WI
Other Years
Research More Models
View more SUVs

© 2026 CoPilot. All Rights Reserved.