Used 2020 Jeep Gladiator for Sale in Chicago, IL
Chicago Search Area
- Dealers in Area
- 1,096
- Gladiators for Sale
- 130
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 • Huntley, IL
$44,944 • 17.5k miles
#1 2019-2021 Jeep Gladiator
It’s an “A+” Buy
- Motivation to Negotiate - Very High
- One Owner, Clean Title, Not a rental or commercial vehicle
- Dealer Rating - 4.5 stars
- Very Low Mileage

2020 Jeep Gladiator Overland 4WD • Burlington, WI
$40,560 • 23.3k miles
#2 2019-2021 Jeep Gladiator
It’s an “A+” Buy
- Motivation to Negotiate - High
- One Owner, Clean Title, Not a rental or commercial vehicle
- Dealer Rating - 4.8 stars
- Very Low Mileage

2021 Jeep Gladiator Overland 4WD • Libertyville, IL
$43,452 • 13.3k miles
#3 2019-2021 Jeep Gladiator
It’s an “A+” Buy
- Motivation to Negotiate - Increasing
- One Owner, Clean Title, Not a rental or commercial vehicle
- Dealer Rating - 4.1 stars
- Very Low Mileage

2021 Jeep Gladiator Rubicon 4WD • Streator, IL
$47,451 • 20.6k miles
#4 2019-2021 Jeep Gladiator
It’s an “A+” Buy
- Motivation to Negotiate - Increasing
- One Owner, Clean Title, Not a rental or commercial vehicle
- Very Low Mileage
- Includes $5,824 Premium Upgrades
2020 Jeep Gladiator Overland 4WD • Huntley, IL
$41,941 • 6.8k miles
#5 2019-2021 Jeep Gladiator
It’s an “A+” Buy
- Motivation to Negotiate - Very High
- One Owner, Clean Title, Not a rental or commercial vehicle
- Dealer Rating - 4.5 stars
- Very Low Mileage
2020 Jeep Gladiator Overland 4WD • Hampshire, IL
$42,500 • 15k miles
#6 2019-2021 Jeep Gladiator
It’s an “A+” Buy
- Motivation to Negotiate - Very High
- One Owner, Clean Title, Not a rental or commercial vehicle
- Very Low Mileage
- Includes $5,220 Premium Upgrades
2021 Jeep Gladiator Willys 4WD • Chicago, IL
$37,350 • 18.7k miles
#7 2019-2021 Jeep Gladiator
It’s an “A+” Buy
- Motivation to Negotiate - Very High
- One Owner, Clean Title, Not a rental or commercial vehicle
- Dealer Rating - 4.4 stars
- Very Low Mileage
2020 Jeep Gladiator Rubicon 4WD • Glencoe, IL
$43,500 • 35.1k miles
#8 2019-2021 Jeep Gladiator
It’s an “A+” Buy
- Motivation to Negotiate - Increasing
- Clean Title, Not a rental or commercial vehicle
- Very Low Mileage
- Includes $4,912 Premium Upgrades
2021 Jeep Gladiator Willys 4WD • Glencoe, IL
$39,199 • 43.9k miles
#9 2019-2021 Jeep Gladiator
It’s an “A+” Buy
- One Owner, Clean Title, Not a rental or commercial vehicle
- Includes $8,636 Premium Upgrades
- Great Price - $3,588 Below Market
2021 Jeep Gladiator Sport 4WD • Merrillville, IN
$36,887 • 10.5k miles
#10 2019-2021 Jeep Gladiator
It’s an “A+” Buy
- Motivation to Negotiate - Increasing
- One Owner, Clean Title, Not a rental or commercial vehicle
- Dealer Rating - 4.3 stars
- Very Low Mileage
2020 Jeep Gladiator Rubicon 4WD • Elgin, IL
$46,500 • 24.6k miles
#11 2019-2021 Jeep Gladiator
It’s an “A+” Buy
- Motivation to Negotiate - Increasing
- Clean Title, Not a rental or commercial vehicle
- Dealer Rating - 4.4 stars
- Very Low Mileage
2020 Jeep Gladiator Overland 4WD • Naperville, IL
$35,785 • 69.2k miles
#12 2019-2021 Jeep Gladiator
It’s an “A+” 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
2020 Jeep Gladiator Sport S 4WD • Waukegan, IL
$31,500 • 64.2k miles
#13 2019-2021 Jeep Gladiator
It’s an “A+” 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
2020 Jeep Gladiator Sport S 4WD • Villa Park, IL
$30,977 • 53k miles
#14 2019-2021 Jeep Gladiator
It’s an “A+” Buy
- Motivation to Negotiate - Very High
- Clean Title
- Includes $5,196 Premium Upgrades
- Great Price - $3,036 Below Market
2021 Jeep Gladiator Mojave 4WD • Chicago, IL
$48,994 • 23.2k miles
#15 2019-2021 Jeep Gladiator
It’s an “A+” Buy
- Motivation to Negotiate - High
- One Owner, Clean Title
- Dealer Rating - 4.5 stars
- Very Low Mileage
2021 Jeep Gladiator Mojave 4WD • Countryside, IL
$46,888 • 25.3k miles
#16 2019-2021 Jeep Gladiator
It’s an “A+” Buy
- One Owner, Clean Title
- Dealer Rating - 4.4 stars
- Very Low Mileage
- Includes $4,468 Premium Upgrades
2021 Jeep Gladiator Mojave 4WD • Naperville, IL
$41,977 • 19.6k miles
#17 2019-2021 Jeep Gladiator
It’s an “A+” Buy
- Motivation to Negotiate - Very High
- One Owner, Clean Title, Not a rental or commercial vehicle
- Dealer Rating - 4.7 stars
- Very Low Mileage
2021 Jeep Gladiator Mojave 4WD • Wheeling, IL
$43,483 • 15k miles
#18 2019-2021 Jeep Gladiator
It’s an “A+” Buy
- Motivation to Negotiate - Increasing
- One Owner, Clean Title, Not a rental or commercial vehicle
- Dealer Rating - 4.3 stars
- Very Low Mileage
2020 Jeep Gladiator Overland 4WD • Chicago, IL
$39,694 • 25.5k miles
#19 2019-2021 Jeep Gladiator
It’s an “A+” Buy
- Motivation to Negotiate - High
- One Owner, Clean Title, Not a rental or commercial vehicle
- Dealer Rating - 4.5 stars
- Very Low Mileage
2021 Jeep Gladiator Willys 4WD • Chicago, IL
$43,994 • 9k miles
#20 2019-2021 Jeep Gladiator
It’s an “A+” Buy
- Motivation to Negotiate - High
- One Owner, Clean Title, Not a rental or commercial vehicle
- Dealer Rating - 4.5 stars
- Very Low Mileage
2021 Jeep Gladiator Willys 4WD • Chicago, IL
$40,995 • 17k miles
#21 2019-2021 Jeep Gladiator
It’s an “A+” Buy
- One Owner, Clean Title, Not a rental or commercial vehicle
- Dealer Rating - 4.3 stars
- Very Low Mileage
- Includes $10,668 Premium Upgrades
2020 Jeep Gladiator Sport S 4WD • St. Charles, IL
$36,988 • 24.6k miles
#22 2019-2021 Jeep Gladiator
It’s an “A+” Buy
- One Owner, Clean Title, Not a rental or commercial vehicle
- Dealer Rating - 4.4 stars
- Very Low Mileage
- Includes $7,384 Premium Upgrades
2020 Jeep Gladiator Sport S 4WD • Racine, WI
$36,529 • 13.1k miles
#23 2019-2021 Jeep Gladiator
It’s an “A+” Buy
- Motivation to Negotiate - Increasing
- One Owner, Clean Title, Not a rental or commercial vehicle
- Dealer Rating - 4.4 stars
- Very Low Mileage
2020 Jeep Gladiator Rubicon 4WD • Elkhart, IN
$43,999 • 42.5k miles
#24 2019-2021 Jeep Gladiator
It’s an “A” Buy
- One Owner, Clean Title, Not a rental or commercial vehicle
- Dealer Rating - 4.5 stars
- Below Average Mileage
- Includes $3,419 Premium Upgrades
2021 Jeep Gladiator High Altitude 4WD • Paw Paw, MI
$46,000 • 10.8k miles
#25 2019-2021 Jeep Gladiator
It’s an “A” Buy
- Clean Title, Not a rental or commercial vehicle
- Dealer Rating - 4.5 stars
- Very Low Mileage
- Includes $9,680 Premium Upgrades
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Jeep Gladiator near Chicago, IL
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