Jeep Gladiator in Chicago, IL
313 Jeep Gladiator listings within 50 miles of Chicago, IL, each scored against every vibe.
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The 12 strongest vibe matches of 313. Every line under a car was generated from that car’s own attributes by the engine, never typed by hand.
2020 Jeep Gladiator Sport S$31,995 · 93,501 mi · MerrillvilleFrat Tailgate99Lift package · Rides high
2026 Jeep Gladiator Texas Trail$50,702 · 10 mi · WoodstockOff-Road Icon99Off-road bloodline · Built to leave pavement
2024 Jeep Gladiator Rubicon$41,995 · 9,910 mi · Saint CharlesIt's a Jeep Thing99Seven slots up front · Trail rated
2026 Jeep Gladiator Texas Trail$43,409 · 5,370 mi · Arlington HeightsIt's a Jeep Thing99Seven slots up front · Trail rated
2022 Jeep Gladiator Rubicon$34,761 · 37,112 mi · ChestertonTrailhead Weekend99Sends power everywhere · Factory off-road trim
2023 Jeep Gladiator Rubicon$42,711 · 16,921 mi · Fox LakeIt's a Jeep Thing99Seven slots up front · Trail rated
2024 Jeep Gladiator Willys$37,296 · 5,961 mi · Oak LawnIt's a Jeep Thing99Seven slots up front · Trail rated
2026 Jeep Gladiator Texas Trail$43,603 · 11 mi · ChicagoOff-Road Icon99Off-road bloodline · Built to leave pavement
2026 Jeep Gladiator Texas Trail$40,525 · 15 mi · Forest ParkIt's a Jeep Thing99Seven slots up front · Trail rated
2023 Jeep Gladiator Rubicon$45,991 · 32 mi · PlanoOff-Road Icon99Off-road bloodline · Built to leave pavement
2021 Jeep Gladiator Rubicon$29,600 · 76,912 mi · SycamoreIt's a Jeep Thing99Seven slots up front · Trail rated
2026 Jeep Gladiator Texas Trail$44,007 · 20 mi · Glendale HeightsOff-Road Icon99Off-road bloodline · Built to leave pavement