1,629 New Jeep Gladiator for Sale Near Chicago, IL
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2026 Jeep Gladiator 85th Anniversary Edition Auto
15 mi.
26 days on market
1C6PJTAG7TL185165
$50,039
Fair Deal
S L Motors
Pulaski, WI
4.5
2026 Jeep Gladiator 85th Anniversary Edition Auto
27 mi.
26 days on market
1C6PJTAG9TL185166
$49,444
Fair Deal
S L Motors
Pulaski, WI
4.5
2026 Jeep Gladiator Mojave Auto
19 mi.
26 days on market
1C6RJTEG8TL187123
$55,179
Fair Deal
S L Motors
Pulaski, WI
4.5
2026 Jeep Gladiator Mojave X Auto
2 mi.
26 days on market
1C6RJTEG9TL189608
$55,154
Great Deal
Jim Riehls Friendly Chrysler Jeep
Warren, MI
4.5
2026 Jeep Gladiator Willys Auto
26 days on market
1C6PJTAG2TL189611
$55,200
Jim Riehls Friendly Chrysler Jeep
Warren, MI
4.5
2026 Jeep Gladiator Sport S Auto
6 mi.
26 days on market
1C6PJTAG3TL188418
$47,140
Fair Deal
Kimberly Car City Cdjr
Davenport, IA
4.6
2026 Jeep Gladiator Willys Auto
8 mi.
26 days on market
1C6PJTAGXTL189470
$50,392
Fair Deal
Charlies Dodge Chrysler Jeep Ram
Maumee, OH
4.4
2026 Jeep Gladiator Sahara Auto
5 mi.
26 days on market
1C6PJTAG1TL189650
$49,318
Fair Deal
Suburban Chrysler Dodge Jeep Ram Of Troy
Troy, MI
4.4
2026 Jeep Gladiator Sahara Auto
5 mi.
26 days on market
1C6PJTAG8TL189645
$47,882
Fair Deal
Suburban Chrysler Dodge Jeep Ram Of Troy
Troy, MI
4.4
2026 Jeep Gladiator Mojave X Auto
26 days on market
1C6RJTEG1TL190090
$67,780
Tom Obrien Cjdr Greenwood
Greenwood, IN
4.6
2026 Jeep Gladiator Shadow OPS Auto
26 days on market
1C6RJTBG9TL178869
$68,950
Fox Chrysler Dodge Jeep Ram
Grand Rapids, MI
4.5
2026 Jeep Gladiator Mojave Auto
5 mi.
26 days on market
1C6RJTEG9TL188460
$50,003
Great Deal
Andy Mohr Chrysler Dodge Jeep Ram
Indianapolis, IN
4.3
2026 Jeep Gladiator Mojave Auto
5 mi.
26 days on market
1C6RJTEG0TL188461
$50,003
Great Deal
Andy Mohr Chrysler Dodge Jeep Ram
Indianapolis, IN
4.3
2026 Jeep Gladiator 85th Anniversary Edition Auto
5 mi.
26 days on market
1C6PJTAG7TL188597
$52,790
Fair Deal
Wetzel Cdjr
Richmond, IN
4.5
2026 Jeep Gladiator 85th Anniversary Edition Auto
7 mi.
26 days on market
1C6PJTAG3TL188709
$46,684
Great Deal
Warsaw Chrysler Dodge Jeep Ram
Warsaw, IN
4.1
2026 Jeep Gladiator Sahara Auto
26 days on market
1C6PJTAGXTL189646
$48,780
Suburban Chrysler Dodge Jeep Ram Of Troy
Troy, MI
4.4
2026 Jeep Gladiator Sahara Auto
26 days on market
1C6PJTAG2TL189656
$53,250
Suburban Chrysler Dodge Jeep Ram Of Troy
Troy, MI
4.4
2026 Jeep Gladiator Sahara Auto
5 mi.
26 days on market
1C6PJTAG9TL189654
$48,782
Fair Deal
Suburban Chrysler Dodge Jeep Ram Of Troy
Troy, MI
4.4
2026 Jeep Gladiator Sahara Auto
5 mi.
26 days on market
1C6PJTAG4TL189643
$47,882
Fair Deal
Suburban Chrysler Dodge Jeep Ram Of Troy
Troy, MI
4.4
2026 Jeep Gladiator 85th Anniversary Edition Auto
5 mi.
26 days on market
1C6PJTAG1TL185727
$48,059
Good Deal
Ed Morse Chrysler Dodge Jeep Ram
Muscatine, IA
4.1
2026 Jeep Gladiator Mojave X Auto
26 days on market
1C6RJTEGXTL189469
$58,180
Charlies Dodge Chrysler Jeep Ram
Maumee, OH
4.4
2026 Jeep Gladiator Mojave X Auto
7 mi.
26 days on market
1C6RJTEG8TL189468
$57,218
Good Deal
Charlies Dodge Chrysler Jeep Ram
Maumee, OH
4.4
2026 Jeep Gladiator Rubicon X Auto
10 mi.
26 days on market
1C6RJTBG1TL188540
$52,662
Great Deal
York Chrysler Dodge Jeep Ram Of Plainfield
Plainfield, IN
4.2
2026 Jeep Gladiator Rubicon X Auto
10 mi.
26 days on market
1C6RJTBG5TL188542
$53,108
Great Deal
York Chrysler Dodge Jeep Ram Of Plainfield
Plainfield, IN
4.2
2026 Jeep Gladiator Sport S Auto
114 mi.
26 days on market
1C6PJTAG5TL163553
$41,954
Good Deal
Richardson Cdjr
Standish, MI
4.2
2026 Jeep Gladiator Mojave X Auto
26 days on market
1C6RJTEG2TL189529
$60,839
Lochmandy Motor Sales Inc Cdjr
Elkhart, IN
3.9
2026 Jeep Gladiator Sport S Auto
26 days on market
1C6PJTAG4TL189531
$49,374
Lochmandy Motor Sales Inc Cdjr
Elkhart, IN
3.9
2026 Jeep Gladiator Sport S Auto
26 days on market
1C6PJTAG6TL189532
$48,379
Lochmandy Motor Sales Inc Cdjr
Elkhart, IN
3.9
2026 Jeep Gladiator 85th Anniversary Edition Auto
15 mi.
26 days on market
1C6PJTAG7TL185165
$50,039
Fair Deal
S L Motors
Pulaski, WI
4.5
2026 Jeep Gladiator 85th Anniversary Edition Auto
27 mi.
26 days on market
1C6PJTAG9TL185166
$49,444
Fair Deal
S L Motors
Pulaski, WI
4.5
2026 Jeep Gladiator Mojave Auto
19 mi.
26 days on market
1C6RJTEG8TL187123
$55,179
Fair Deal
S L Motors
Pulaski, WI
4.5
2026 Jeep Gladiator Mojave X Auto
2 mi.
26 days on market
1C6RJTEG9TL189608
$55,154
Great Deal
Jim Riehls Friendly Chrysler Jeep
Warren, MI
4.5
2026 Jeep Gladiator Willys Auto
26 days on market
1C6PJTAG2TL189611
$55,200
Jim Riehls Friendly Chrysler Jeep
Warren, MI
4.5
2026 Jeep Gladiator Sport S Auto
6 mi.
26 days on market
1C6PJTAG3TL188418
$47,140
Fair Deal
Kimberly Car City Cdjr
Davenport, IA
4.6
2026 Jeep Gladiator Willys Auto
8 mi.
26 days on market
1C6PJTAGXTL189470
$50,392
Fair Deal
Charlies Dodge Chrysler Jeep Ram
Maumee, OH
4.4
2026 Jeep Gladiator Sahara Auto
5 mi.
26 days on market
1C6PJTAG1TL189650
$49,318
Fair Deal
Suburban Chrysler Dodge Jeep Ram Of Troy
Troy, MI
4.4
2026 Jeep Gladiator Sahara Auto
5 mi.
26 days on market
1C6PJTAG8TL189645
$47,882
Fair Deal
Suburban Chrysler Dodge Jeep Ram Of Troy
Troy, MI
4.4
2026 Jeep Gladiator Mojave X Auto
26 days on market
1C6RJTEG1TL190090
$67,780
Tom Obrien Cjdr Greenwood
Greenwood, IN
4.6
2026 Jeep Gladiator Shadow OPS Auto
26 days on market
1C6RJTBG9TL178869
$68,950
Fox Chrysler Dodge Jeep Ram
Grand Rapids, MI
4.5
2026 Jeep Gladiator Mojave Auto
5 mi.
26 days on market
1C6RJTEG9TL188460
$50,003
Great Deal
Andy Mohr Chrysler Dodge Jeep Ram
Indianapolis, IN
4.3
2026 Jeep Gladiator Mojave Auto
5 mi.
26 days on market
1C6RJTEG0TL188461
$50,003
Great Deal
Andy Mohr Chrysler Dodge Jeep Ram
Indianapolis, IN
4.3
2026 Jeep Gladiator 85th Anniversary Edition Auto
5 mi.
26 days on market
1C6PJTAG7TL188597
$52,790
Fair Deal
Wetzel Cdjr
Richmond, IN
4.5
2026 Jeep Gladiator 85th Anniversary Edition Auto
7 mi.
26 days on market
1C6PJTAG3TL188709
$46,684
Great Deal
Warsaw Chrysler Dodge Jeep Ram
Warsaw, IN
4.1
2026 Jeep Gladiator Sahara Auto
26 days on market
1C6PJTAGXTL189646
$48,780
Suburban Chrysler Dodge Jeep Ram Of Troy
Troy, MI
4.4
2026 Jeep Gladiator Sahara Auto
26 days on market
1C6PJTAG2TL189656
$53,250
Suburban Chrysler Dodge Jeep Ram Of Troy
Troy, MI
4.4
2026 Jeep Gladiator Sahara Auto
5 mi.
26 days on market
1C6PJTAG9TL189654
$48,782
Fair Deal
Suburban Chrysler Dodge Jeep Ram Of Troy
Troy, MI
4.4
2026 Jeep Gladiator Sahara Auto
5 mi.
26 days on market
1C6PJTAG4TL189643
$47,882
Fair Deal
Suburban Chrysler Dodge Jeep Ram Of Troy
Troy, MI
4.4
2026 Jeep Gladiator 85th Anniversary Edition Auto
5 mi.
26 days on market
1C6PJTAG1TL185727
$48,059
Good Deal
Ed Morse Chrysler Dodge Jeep Ram
Muscatine, IA
4.1
2026 Jeep Gladiator Mojave X Auto
26 days on market
1C6RJTEGXTL189469
$58,180
Charlies Dodge Chrysler Jeep Ram
Maumee, OH
4.4
2026 Jeep Gladiator Mojave X Auto
7 mi.
26 days on market
1C6RJTEG8TL189468
$57,218
Good Deal
Charlies Dodge Chrysler Jeep Ram
Maumee, OH
4.4
2026 Jeep Gladiator Rubicon X Auto
10 mi.
26 days on market
1C6RJTBG1TL188540
$52,662
Great Deal
York Chrysler Dodge Jeep Ram Of Plainfield
Plainfield, IN
4.2
2026 Jeep Gladiator Rubicon X Auto
10 mi.
26 days on market
1C6RJTBG5TL188542
$53,108
Great Deal
York Chrysler Dodge Jeep Ram Of Plainfield
Plainfield, IN
4.2
2026 Jeep Gladiator Sport S Auto
114 mi.
26 days on market
1C6PJTAG5TL163553
$41,954
Good Deal
Richardson Cdjr
Standish, MI
4.2
2026 Jeep Gladiator Mojave X Auto
26 days on market
1C6RJTEG2TL189529
$60,839
Lochmandy Motor Sales Inc Cdjr
Elkhart, IN
3.9
2026 Jeep Gladiator Sport S Auto
26 days on market
1C6PJTAG4TL189531
$49,374
Lochmandy Motor Sales Inc Cdjr
Elkhart, IN
3.9
2026 Jeep Gladiator Sport S Auto
26 days on market
1C6PJTAG6TL189532
$48,379
Lochmandy Motor Sales Inc Cdjr
Elkhart, IN
3.9
Find New Jeep Gladiator in Chicago, IL
The Jeep Gladiator is offered in the U.S. lineup in the Pickup configuration. Differences mainly come down to trim, features, and drivetrain.