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Used 2020 Jeep Gladiator for Sale in Chicago, IL

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Top Ranked Used 2019-2021 Jeep Gladiators near Chicago

Ranked by Most Car for Your Money

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2020 Jeep Gladiator Rubicon 4WD photo
1
Price Drop

2020 Jeep Gladiator Rubicon 4WD Huntley, IL

$44,944 17.5k miles

#1 2019-2021 Jeep Gladiator

It’s anA+” Buy

  • Motivation to Negotiate - Very High
  • One Owner, Clean Title, Not a rental or commercial vehicle
  • Dealer Rating - 4.5 stars
  • Very Low Mileage
See more about this car
2020 Jeep Gladiator Overland 4WD photo
2

2020 Jeep Gladiator Overland 4WD Burlington, WI

$40,560 23.3k miles

#2 2019-2021 Jeep Gladiator

It’s anA+” Buy

  • Motivation to Negotiate - High
  • One Owner, Clean Title, Not a rental or commercial vehicle
  • Dealer Rating - 4.8 stars
  • Very Low Mileage
See more about this car
2021 Jeep Gladiator Overland 4WD photo
3

2021 Jeep Gladiator Overland 4WD Libertyville, IL

$43,452 13.3k miles

#3 2019-2021 Jeep Gladiator

It’s anA+” Buy

  • Motivation to Negotiate - Increasing
  • One Owner, Clean Title, Not a rental or commercial vehicle
  • Dealer Rating - 4.1 stars
  • Very Low Mileage
See more about this car
2021 Jeep Gladiator Rubicon 4WD photo
4
Price Drop

2021 Jeep Gladiator Rubicon 4WD Streator, IL

$47,451 20.6k miles

#4 2019-2021 Jeep Gladiator

It’s anA+” Buy

  • Motivation to Negotiate - Increasing
  • One Owner, Clean Title, Not a rental or commercial vehicle
  • Very Low Mileage
  • Includes $5,824 Premium Upgrades
See more about this car
2020 Jeep Gladiator Overland 4WD photo
5
Price Drop

2020 Jeep Gladiator Overland 4WD Huntley, IL

$41,941 6.8k miles

#5 2019-2021 Jeep Gladiator

It’s anA+” Buy

  • Motivation to Negotiate - Very High
  • One Owner, Clean Title, Not a rental or commercial vehicle
  • Dealer Rating - 4.5 stars
  • Very Low Mileage
See more about this car
2020 Jeep Gladiator Overland 4WD photo
6
Price Drop

2020 Jeep Gladiator Overland 4WD Hampshire, IL

$42,500 15k miles

#6 2019-2021 Jeep Gladiator

It’s anA+” Buy

  • Motivation to Negotiate - Very High
  • One Owner, Clean Title, Not a rental or commercial vehicle
  • Very Low Mileage
  • Includes $5,220 Premium Upgrades
See more about this car
2021 Jeep Gladiator Willys 4WD photo
7
Price Drop

2021 Jeep Gladiator Willys 4WD Chicago, IL

$37,350 18.7k miles

#7 2019-2021 Jeep Gladiator

It’s anA+” Buy

  • Motivation to Negotiate - Very High
  • One Owner, Clean Title, Not a rental or commercial vehicle
  • Dealer Rating - 4.4 stars
  • Very Low Mileage
See more about this car
2020 Jeep Gladiator Rubicon 4WD photo
8
Price Drop

2020 Jeep Gladiator Rubicon 4WD Glencoe, IL

$43,500 35.1k miles

#8 2019-2021 Jeep Gladiator

It’s anA+” Buy

  • Motivation to Negotiate - Increasing
  • Clean Title, Not a rental or commercial vehicle
  • Very Low Mileage
  • Includes $4,912 Premium Upgrades
See more about this car
2021 Jeep Gladiator Willys 4WD photo
9
Price Drop

2021 Jeep Gladiator Willys 4WD Glencoe, IL

$39,199 43.9k miles

#9 2019-2021 Jeep Gladiator

It’s anA+” Buy

  • One Owner, Clean Title, Not a rental or commercial vehicle
  • Includes $8,636 Premium Upgrades
  • Great Price - $3,588 Below Market
See more about this car
2021 Jeep Gladiator Sport 4WD photo
10
Price Drop

2021 Jeep Gladiator Sport 4WD Merrillville, IN

$36,887 10.5k miles

#10 2019-2021 Jeep Gladiator

It’s anA+” Buy

  • Motivation to Negotiate - Increasing
  • One Owner, Clean Title, Not a rental or commercial vehicle
  • Dealer Rating - 4.3 stars
  • Very Low Mileage
See more about this car
2020 Jeep Gladiator Rubicon 4WD photo
11
Price Drop

2020 Jeep Gladiator Rubicon 4WD Elgin, IL

$46,500 24.6k miles

#11 2019-2021 Jeep Gladiator

It’s anA+” Buy

  • Motivation to Negotiate - Increasing
  • Clean Title, Not a rental or commercial vehicle
  • Dealer Rating - 4.4 stars
  • Very Low Mileage
See more about this car
2020 Jeep Gladiator Overland 4WD photo
12
Price Drop

2020 Jeep Gladiator Overland 4WD Naperville, IL

$35,785 69.2k miles

#12 2019-2021 Jeep Gladiator

It’s anA+” Buy

  • Motivation to Negotiate - Increasing
  • One Owner, Clean Title, Not a rental or commercial vehicle
  • Dealer Rating - 4.0 stars
  • Includes $4,210 Premium Upgrades
See more about this car
2020 Jeep Gladiator Sport S 4WD photo
13

2020 Jeep Gladiator Sport S 4WD Waukegan, IL

$31,500 64.2k miles

#13 2019-2021 Jeep Gladiator

It’s anA+” Buy

  • Clean Title, Not a rental or commercial vehicle
  • Dealer Rating - 4.4 stars
  • Includes $5,363 Premium Upgrades
  • Great Price - $12,103 Below Market
See more about this car
2020 Jeep Gladiator Sport S 4WD photo
14
Price Drop

2020 Jeep Gladiator Sport S 4WD Villa Park, IL

$30,977 53k miles

#14 2019-2021 Jeep Gladiator

It’s anA+” Buy

  • Motivation to Negotiate - Very High
  • Clean Title
  • Includes $5,196 Premium Upgrades
  • Great Price - $3,036 Below Market
See more about this car
2021 Jeep Gladiator Mojave 4WD photo
15
Price Drop

2021 Jeep Gladiator Mojave 4WD Chicago, IL

$48,994 23.2k miles

#15 2019-2021 Jeep Gladiator

It’s anA+” Buy

  • Motivation to Negotiate - High
  • One Owner, Clean Title
  • Dealer Rating - 4.5 stars
  • Very Low Mileage
See more about this car
2021 Jeep Gladiator Mojave 4WD photo
16
Price Drop

2021 Jeep Gladiator Mojave 4WD Countryside, IL

$46,888 25.3k miles

#16 2019-2021 Jeep Gladiator

It’s anA+” Buy

  • One Owner, Clean Title
  • Dealer Rating - 4.4 stars
  • Very Low Mileage
  • Includes $4,468 Premium Upgrades
See more about this car
2021 Jeep Gladiator Mojave 4WD photo
17
Price Drop

2021 Jeep Gladiator Mojave 4WD Naperville, IL

$41,977 19.6k miles

#17 2019-2021 Jeep Gladiator

It’s anA+” Buy

  • Motivation to Negotiate - Very High
  • One Owner, Clean Title, Not a rental or commercial vehicle
  • Dealer Rating - 4.7 stars
  • Very Low Mileage
See more about this car
2021 Jeep Gladiator Mojave 4WD photo
18
Price Drop

2021 Jeep Gladiator Mojave 4WD Wheeling, IL

$43,483 15k miles

#18 2019-2021 Jeep Gladiator

It’s anA+” Buy

  • Motivation to Negotiate - Increasing
  • One Owner, Clean Title, Not a rental or commercial vehicle
  • Dealer Rating - 4.3 stars
  • Very Low Mileage
See more about this car
2020 Jeep Gladiator Overland 4WD photo
19
Price Drop

2020 Jeep Gladiator Overland 4WD Chicago, IL

$39,694 25.5k miles

#19 2019-2021 Jeep Gladiator

It’s anA+” Buy

  • Motivation to Negotiate - High
  • One Owner, Clean Title, Not a rental or commercial vehicle
  • Dealer Rating - 4.5 stars
  • Very Low Mileage
See more about this car
2021 Jeep Gladiator Willys 4WD photo
20
Price Drop

2021 Jeep Gladiator Willys 4WD Chicago, IL

$43,994 9k miles

#20 2019-2021 Jeep Gladiator

It’s anA+” Buy

  • Motivation to Negotiate - High
  • One Owner, Clean Title, Not a rental or commercial vehicle
  • Dealer Rating - 4.5 stars
  • Very Low Mileage
See more about this car
2021 Jeep Gladiator Willys 4WD photo
21

2021 Jeep Gladiator Willys 4WD Chicago, IL

$40,995 17k miles

#21 2019-2021 Jeep Gladiator

It’s anA+” Buy

  • One Owner, Clean Title, Not a rental or commercial vehicle
  • Dealer Rating - 4.3 stars
  • Very Low Mileage
  • Includes $10,668 Premium Upgrades
See more about this car
2020 Jeep Gladiator Sport S 4WD photo
22

2020 Jeep Gladiator Sport S 4WD St. Charles, IL

$36,988 24.6k miles

#22 2019-2021 Jeep Gladiator

It’s anA+” Buy

  • One Owner, Clean Title, Not a rental or commercial vehicle
  • Dealer Rating - 4.4 stars
  • Very Low Mileage
  • Includes $7,384 Premium Upgrades
See more about this car
2020 Jeep Gladiator Sport S 4WD photo
23
Price Drop

2020 Jeep Gladiator Sport S 4WD Racine, WI

$36,529 13.1k miles

#23 2019-2021 Jeep Gladiator

It’s anA+” Buy

  • Motivation to Negotiate - Increasing
  • One Owner, Clean Title, Not a rental or commercial vehicle
  • Dealer Rating - 4.4 stars
  • Very Low Mileage
See more about this car
2020 Jeep Gladiator Rubicon 4WD photo
24

2020 Jeep Gladiator Rubicon 4WD Elkhart, IN

$43,999 42.5k miles

#24 2019-2021 Jeep Gladiator

It’s anA” Buy

  • One Owner, Clean Title, Not a rental or commercial vehicle
  • Dealer Rating - 4.5 stars
  • Below Average Mileage
  • Includes $3,419 Premium Upgrades
See more about this car
2021 Jeep Gladiator High Altitude 4WD photo
25

2021 Jeep Gladiator High Altitude 4WD Paw Paw, MI

$46,000 10.8k miles

#25 2019-2021 Jeep Gladiator

It’s anA” Buy

  • Clean Title, Not a rental or commercial vehicle
  • Dealer Rating - 4.5 stars
  • Very Low Mileage
  • Includes $9,680 Premium Upgrades
See more about this car
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