Used Jeep Gladiator for Sale near Chicago, IL

## Summary - With 417 currently listed for sale near Chicago, IL and an **average price of $30,222.00**, 33.6% of 2021 Jeep Gladiators for sale on CarGurus are rated as good or great deals. - **Favorably reviewed:** Owners rated the 2021 Jeep Gladiator 4.8 / 5 stars. - **101.7% of 2021 Gladiator models on CarGurus are accident free**. - The 2021 Jeep Gladiator now offers a turbo-diesel option, enhancing its towing capacity and fuel efficiency while maintaining its rugged off-road capabilities. ## Why it stands out The 2021 Jeep Gladiator distinguishes itself in the midsize pickup market with its blend of practicality, personalization, and adventurous spirit. Built on the successful Wrangler platform, it features a removable roof and doors for that authentic open-air experience. This model year introduced a turbo-diesel engine option, significantly enhancing low-end torque and fuel efficiency, making it an ideal choice for both work and play. With numerous aftermarket accessories and special editions available, the Gladiator appeals to those who seek to customize their vehicle for off-road adventures, all while providing robust hauling capabilities. ## Other model years to consider - **[2020 Jeep Gladiator](https://www.cargurus.com/Cars/l-Used-2020-Jeep-Gladiator-Chicago-c28934_L7510)** - Average price: $26,777.00 - Good/great deal percentage: 31.6% - User rating: 4.72 / 5 - Total listings: 294 - **[2022 Jeep Gladiator](https://www.cargurus.com/Cars/l-Used-2022-Jeep-Gladiator-Chicago-c32007_L7510)** - Average price: $32,685.00 - Good/great deal percentage: 34.1% - User rating: 4.4 / 5 - Total listings: 396 - **[2023 Jeep Gladiator](https://www.cargurus.com/Cars/l-Used-2023-Jeep-Gladiator-Chicago-c32473_L7510)** - Average price: $35,453.00 - Good/great deal percentage: 36.1% - User rating: 4.84 / 5 - Total listings: 255 These recommendations are based on CarGurus' proprietary market data from March 24, 2026, CarGurus experts' opinions, and generative AI.