CarGurus Logo Homepage Link
  • Buy
    • Used cars
    • New cars
    • Certified pre-owned
    • Start your purchase online
    • Dealerships near me
  • Sell
    • Sell my car
    • Sell my car FAQs
  • Finance
    • Prequalify for financing
    • How does it work?
    • Financing FAQs
  • Research
    • Test drive reviews
    • Price trends
    • Tips & advice
    • Electric cars
    • Compare cars
  • Discover
    The latest way to shop:
    smarter research, better
    listings.
  • Saved cars & searches
  • Sign in / Register
    • My account
    • Saved searches
    • Saved cars
    • Recommended cars
    • Browsing history
    • Financing dashboard
      • United States (EN)
      • Estados Unidos (ES)
      • Canada (EN)
      • Canada (FR)
      • United Kingdom

Used 1999 Jeep Cherokee for Sale near Milwaukee, WI

712 results
Milwaukee, WI
2022 Jeep Cherokee Trailhawk 4WD Zeigler Toyota of Racine

2022 Jeep Cherokee

Trailhawk 4WD

35,075 miles

$24,749

Fair Deal
Mt Pleasant, WI
22 mi away
Year:
2022
Make:
Jeep
Model:
Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
271 hp 3.2L V6
Exterior color:
Diamond Black Crystal Pearlcoat
Combined gas mileage:
21 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
9-Speed Automatic
Mileage:
35,075
Stock number:
ND513414
VIN:
1C4PJMBX8ND513414

Sponsored

2021 Jeep Cherokee Trailhawk 4WD

2021 Jeep Cherokee

Trailhawk 4WD

18,515 miles

$25,377

Fair Deal
Antioch, IL
40 mi away
Year:
2021
Make:
Jeep
Model:
Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
271 hp 3.2L V6
Exterior color:
Bright White Clearcoat
Combined gas mileage:
21 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
9-Speed Automatic
Mileage:
18,515
Stock number:
20916P
VIN:
1C4PJMBX9MD222967

Sponsored

2020 Jeep Cherokee Limited 4WD

2020 Jeep Cherokee

Limited 4WD

74,696 miles

$17,260

Good Deal
Gurnee, IL
45 mi away
Year:
2020
Make:
Jeep
Model:
Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
271 hp 3.2L V6
Exterior color:
Diamond Black Crystal Pearlcoat
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
9-Speed Automatic
Mileage:
74,696
Stock number:
GV30204
VIN:
1C4PJMDX2LD567124

Sponsored

2019 Jeep Cherokee Latitude FWD

2019 Jeep Cherokee

Latitude FWD

42,721 miles

$15,738

Good Deal
Milwaukee, WI
10 mi away
Year:
2019
Make:
Jeep
Model:
Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
180 hp 2.4L I4
Exterior color:
Billet Silver Metallic Clearcoat
Combined gas mileage:
26 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
9-Speed Automatic
Mileage:
42,721
Stock number:
J25117B
VIN:
1C4PJLCBXKD411640

2020 Jeep Cherokee Trailhawk 4WD

2020 Jeep Cherokee

Trailhawk 4WD

75,842 miles

$17,250

Good Deal
Ringwood, IL
48 mi away
Year:
2020
Make:
Jeep
Model:
Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
271 hp 3.2L V6
Exterior color:
Hydro Blue Pearlcoat
Combined gas mileage:
21 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
9-Speed Automatic
Mileage:
75,842
Stock number:
CP7252
VIN:
1C4PJMBX8LD647157

2019 Jeep Cherokee High Altitude 4WD

2019 Jeep Cherokee

High Altitude 4WD

95,125 miles

$15,995

Great Deal
Certified Pre-Owned
Milwaukee, WI
7 mi away
Year:
2019
Make:
Jeep
Model:
Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
271 hp 3.2L V6
Exterior color:
Pearl White Pearlcoat
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black Leather
Transmission:
Automatic
Mileage:
95,125
Stock number:
N25214AA
VIN:
1C4PJMDX1KD398423

Preparing for a close up...

Photos coming soon

2016 Jeep Cherokee

Latitude FWD

178,227 miles

$6,995

Fair Deal
Kenosha, WI
34 mi away
Year:
2016
Make:
Jeep
Model:
Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
180 hp 2.4L I4
Exterior color:
Gray
Combined gas mileage:
26 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
9-Speed Automatic
Mileage:
178,227
Stock number:
5777
VIN:
1C4PJLCB8GW303321

Preparing for a close up...

Photos coming soon

2016 Jeep Cherokee

Limited 4WD

128,679 miles

$9,995

Fair Deal
Milwaukee, WI
7 mi away
Year:
2016
Make:
Jeep
Model:
Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
271 hp 3.2L V6
Exterior color:
White
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
9-Speed Automatic
Mileage:
128,679
Stock number:
#238
VIN:
1C4PJMDS2GW120744

Preparing for a close up...

Photos coming soon

2020 Jeep Cherokee

Trailhawk 4WD

10,589 miles

$22,697

Good Deal
Lindenhurst, IL
45 mi away
Year:
2020
Make:
Jeep
Model:
Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
271 hp 3.2L V6
Exterior color:
Diamond Black Crystal Pearlcoat
Combined gas mileage:
21 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
9-Speed Automatic
Mileage:
10,589
Stock number:
P6335
VIN:
1C4PJMBX9LD632599

Preparing for a close up...

Photos coming soon

2014 Jeep Cherokee

Latitude 4WD

115,494 miles

$6,999

Great Deal
Milwaukee, WI
6 mi away
Year:
2014
Make:
Jeep
Model:
Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
180 hp 2.4L I4
Exterior color:
Black
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
9-Speed Automatic
Mileage:
115,494
Stock number:
12634
VIN:
1C4PJMCB3EW224979

Preparing for a close up...

Photos coming soon

2016 Jeep Cherokee

Latitude 4WD

125,561 miles

$9,802

Good Deal
Plymouth, WI
50 mi away
Year:
2016
Make:
Jeep
Model:
Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
271 hp 3.2L V6
Exterior color:
Brilliant Black Crystal Pearlcoat
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
9-Speed Automatic
Mileage:
125,561
Stock number:
G716170
VIN:
1C4PJMCS8GW168430

Preparing for a close up...

Photos coming soon

2019 Jeep Cherokee

Limited 4WD

55,861 miles

$17,550

Good Deal
Oconomowoc, WI
29 mi away
Year:
2019
Make:
Jeep
Model:
Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
271 hp 3.2L V6
Exterior color:
Red (Maroon)
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
9-Speed Automatic
Mileage:
55,861
Stock number:
5781
VIN:
1C4PJMDX1KD336035

Preparing for a close up...

Photos coming soon

2017 Jeep Cherokee

Trailhawk 4WD

144,996 miles

$8,999

Great Deal
Milwaukee, WI
6 mi away
Year:
2017
Make:
Jeep
Model:
Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
271 hp 3.2L V6
Exterior color:
Gray
Combined gas mileage:
21 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
9-Speed Automatic
Mileage:
144,996
Stock number:
12247
VIN:
1C4PJMBS5HW585202

Preparing for a close up...

Photos coming soon

2019 Jeep Cherokee

Latitude 4WD

69,933 miles

$14,995

Good Deal
Fort Atkinson, WI
47 mi away
Year:
2019
Make:
Jeep
Model:
Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
271 hp 3.2L V6
Exterior color:
Red
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
9-Speed Automatic
Mileage:
69,933
Stock number:
10732
VIN:
1C4PJMCX1KD157589

Preparing for a close up...

Photos coming soon

2019 Jeep Cherokee

Latitude Plus 4WD

107,955 miles

$10,995

Great Deal
West Bend, WI
32 mi away
Year:
2019
Make:
Jeep
Model:
Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
270 hp 2L I4
Exterior color:
Gold
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
9-Speed Automatic
Mileage:
107,955
Stock number:
AR116402
VIN:
1C4PJMLN9KD116402

Preparing for a close up...

Photos coming soon

2020 Jeep Cherokee

Latitude Plus 4WD

46,654 miles

$17,990

Good Deal
Kenosha, WI
33 mi away
Year:
2020
Make:
Jeep
Model:
Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
180 hp 2.4L I4
Exterior color:
Slate Blue Pearlcoat
Combined gas mileage:
25 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
9-Speed Automatic
Mileage:
46,654
Stock number:
T252638A
VIN:
1C4PJMLB6LD599144

Preparing for a close up...

Photos coming soon

2021 Jeep Cherokee

Limited 4WD

74,681 miles

$19,762

Fair Deal
Milwaukee, WI
10 mi away
Year:
2021
Make:
Jeep
Model:
Cherokee
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
271 hp 3.2L V6
Exterior color:
Sting-Gray Clearcoat
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
9-Speed Automatic
Mileage:
74,681
Stock number:
CPS8842A
VIN:
1C4PJMDXXMD174795

Sponsored

  1. Home
  2. / Used Cars
  3. / Jeep Cherokee
  4. / Sport 2-Door 4WD
  5. / Wisconsin
  6. / Milwaukee
Reviews

4.4 Overall rating

(3 reviews)
Wendaline F
4.0
Reviewed a 1999 Jeep Sport 2-Door 4WD on Apr 26, 2008

This car can and did take every sort of abuse. It went through my, both my sisters, dads, and granparents hands and SURVIVED to go on to another home. This auto is very reliable and great for outdoor enthusiasts. It has room, room, and more room for camping gear, passengers, suit cases, and the such. It's steering and acceleration are a bit harder than some but its brakes are great. It doesn't (or ours didn't) have power locks or windows but, really, who needs those? It's also not very peppy or quick but, again, its an outdoor car and not designed for that.

Max S
4.0
Reviewed a 1999 Jeep Sport 2-Door 4WD on Apr 02, 2010

solid performance everything holds up with trails as well as many miles on the highway. funfaktor=11/10. Watch out for failing door latches from saggy hinges, other than that keep an eye out for rust and drive it like ya stole it!

Christopher L
5.0
Reviewed a 1999 Jeep Sport 2-Door 4WD on Jul 14, 2009

its a little back jeep with 31/10.50 15's without a lift ,soon to be 6" taller... i've raced it and damn its fast, some muscle cars and any tuners are easy. i have new brakes front and back so i can stop on a dime and all new steering components so even with a high center of gravity i handles extremely well, its built like a tank i actually worte off a caravan with it last winter and my boss just noticed it last week when i park right beside him, other than a few skratches and dents from 4x4ing it looks great black on black with big mud tires and MAG wheels.... other then the odd breakdown on the trail gas is my only issue its a farily good sized suv so yeah it sucks gas.... its my daily driver and my weekend warrior and its a blast to drive i recomend everyone have at least one

  • 2001 Jeep Cherokee Sport 2-Door 4WD

  • 2000 Jeep Cherokee Sport 2-Door 4WD

  • 1998 Jeep Cherokee Sport 2-Door 4WD

  • 1997 Jeep Cherokee Sport 2-Door 4WD

  • 1996 Jeep Cherokee Sport 2-Door 4WD

  • All Used Cars

  • Manual Transmission Cars

  • Luxury Cars

  • Cars with Red Interior

  • Cheap Manual Cars

  • Hybrid Cars

  • Sports Cars

  • Electric SUVs

  • Cheap Trucks

  • Small Cars

  • Third Row SUVs

  • Three Quarter Ton Trucks

  • Lifted Trucks

  • Manual Transmission Trucks

  • Diesel Trucks

  • Hybrid SUVs

  • Dually Trucks

  • One Ton Trucks

  • Cheap SUVs

  • Lifted Ford Trucks

  • 4x4 Trucks

  • Work Trucks

  • AWD SUVs

  • Ford Trucks

  • Chevrolet Trucks

  • Toyota Trucks

  • Trucks Under $10,000

  • Cars Under $15,000

  • Sports Cars Under $20,000

  • Trucks Under $20,000

  • Used Sedans for Sale with Low Mileage

  • Used SUVs / Crossovers for Sale with Low Mileage

  • Used Hatchbacks for Sale with Low Mileage

  • Used Convertibles for Sale with Low Mileage

  • Used Vans for Sale with Low Mileage

  • Used Minivans for Sale with Low Mileage

  • Used Pickup Trucks for Sale with Low Mileage

  • Used Coupes for Sale with Low Mileage

  • Used Wagons for Sale with Low Mileage

  • Miller Motor Sales

  • Boucher Volkswagen Marketplace

  • Griffin's Hub Chrysler Jeep Dodge

  • John Amato Chrysler Dodge Jeep Ram

  • Martin's Chrysler Dodge Jeep RAM

Connect with us
Download our app
Download on the App Store Get it on Google Play
  • Company
  • About CarGurus
  • Our team
  • Press
  • Investor relations
  • Price trends
  • Careers
  • Advertise with CarGurus
  • For dealers
  • Dealer signup
  • Dealer resources
  • Terms
  • Terms of use
  • Privacy policy
  • Interest-based ads
  • Security
  • Help
  • Help center
  • Contact us
Click for the BBB Business Review of this Auto Listing Service in Cambridge MA
    • United States (EN)
    • Estados Unidos (ES)
    • Canada (EN)
    • Canada (FR)
    • United Kingdom

© 2025 CarGurus, Inc., All Rights Reserved.