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New & Used 2025 Jeep Gladiator for Sale near Chicago, IL

278 results

CarGurus Analysis:

2025 Jeep Gladiator

5.0

  • With 116 currently listed for sale near Chicago, IL and an average price of $40,512.00, 17.2% of 2025 Jeep Gladiators for sale on CarGurus are rated as good or great deals.

  • Favorably reviewed: Owners rated the 2025 Jeep Gladiator 5 / 5 stars.

  • 100.0% of 2025 Gladiator models on CarGurus are accident free.

  • The 2025 Jeep Gladiator is known for its unique combination of being a pickup truck, convertible, and off-roader, capable of towing up to 7,700 pounds and featuring a cargo bed designed for versatility.

Research summarized using AI

 

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CarGurus Analysis: 2025 Jeep Gladiator

5.3
of 10
overall
Look and feel7/10
Technology6/10
Performance4/10
Safety3/10
Form & function7/10
Cost effectiveness5/10
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Summary

  • With 116 currently listed for sale near Chicago, IL and an average price of $40,512.00, 17.2% of 2025 Jeep Gladiators for sale on CarGurus are rated as good or great deals.

  • Favorably reviewed: Owners rated the 2025 Jeep Gladiator 5 / 5 stars.

  • 100.0% of 2025 Gladiator models on CarGurus are accident free.

  • The 2025 Jeep Gladiator is known for its unique combination of being a pickup truck, convertible, and off-roader, capable of towing up to 7,700 pounds and featuring a cargo bed designed for versatility.

Why it stands out

The 2025 Jeep Gladiator sets itself apart in the midsize truck segment by blending the classic Jeep experience with the utility of a pickup. Its convertible top and removable doors offer a distinctive open-air driving experience not found in competitors, making it an exciting choice for adventurous drivers. Despite some limitations in towing and payload compared to rivals, the Gladiator's off-road capability remains impressive, especially with specific trims like the Mojave, which is built for desert conditions. This model introduces new colors and maintains popular features like the powerful Pentastar V6 engine, ensuring a robust driving dynamic on and off the road. While it excels in off-road scenarios, prospective buyers should be aware of its less competitive fuel economy and limited advanced safety options.

Other model years to consider

  • 2021 Jeep Gladiator

    • Average price: $31,094.00
    • Good/great deal percentage: 20.5%
    • User rating: 5 / 5
    • Total listings: 443
  • 2020 Jeep Gladiator

    • Average price: $28,409.00
    • Good/great deal percentage: 20.6%
    • User rating: 4.83 / 5
    • Total listings: 311
  • 2023 Jeep Gladiator

    • Average price: $33,259.00
    • Good/great deal percentage: 19.1%
    • User rating: 4.82 / 5
    • Total listings: 288

This analysis is based on CarGurus' proprietary market data from June 2, 2026, CarGurus experts' opinions, and generative AI.

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