Used 2021 Jeep Cherokee for Sale near Winnipeg, MB
34 results
CarGurus Analysis:
2021 Jeep Cherokee
With 31 currently listed for sale near Winnipeg, MB and an average price of $24,935.00 CAD, 32.3% of 2021 Jeep Cherokees for sale on CarGurus are rated as good or great deals.
Favourably reviewed: Owners rated the 2021 Jeep Cherokee 4.8 / 5 stars.
100.0% of 2021 Cherokee models on CarGurus are accident free.
The 2021 Jeep Cherokee is praised for its great value, smooth ride, and numerous safety features, particularly in the Trailhawk trim, which is noted for its off-road capabilities.
CarGurus Analysis: 2021 Jeep Cherokee
Summary
With 31 currently listed for sale near Winnipeg, MB and an average price of $24,935.00 CAD, 32.3% of 2021 Jeep Cherokees for sale on CarGurus are rated as good or great deals.
Favourably reviewed: Owners rated the 2021 Jeep Cherokee 4.8 / 5 stars.
100.0% of 2021 Cherokee models on CarGurus are accident free.
The 2021 Jeep Cherokee is praised for its great value, smooth ride, and numerous safety features, particularly in the Trailhawk trim, which is noted for its off-road capabilities.
Why it stands out
The 2021 Jeep Cherokee distinguishes itself with a blend of comfort, advanced technology, and off-road prowess, making it a compelling choice for buyers seeking versatility. Its smooth ride quality and robust safety features enhance its appeal, particularly for families and adventure enthusiasts. The Trailhawk trim stands out with its enhanced off-road capabilities, allowing drivers to tackle rugged terrains with confidence. While some users express disappointment over the absence of certain features like Remote Start and a powered tailgate, the overall satisfaction remains high, as reflected in the impressive user rating of 4.8 / 5 stars. The 2021 model also boasts a 100% accident-free record, ensuring peace of mind for potential buyers.
Other model years to consider
- Average price: $29,625.00 CAD
- Good/great deal percentage: 27.6%
- User rating: 5 / 5
- Total listings: 29
- Average price: $32,784.00 CAD
- Good/great deal percentage: 25.0%
- User rating: 4.5 / 5
- Total listings: 20
This analysis is based on CarGurus' proprietary market data from July 8, 2026, CarGurus experts' opinions, and generative AI.
4.8 Overall rating
Filter by rating
Xing F
Reviewed a 2021 Jeep Cherokee on Oct 22, 2024
The 2021 Jeep Cherokee is a versatile compact SUV that excels in off-road performance, particularly in the Trailhawk trim, thanks to its advanced 4x4 system and terrain management features.
Todd R
Reviewed a 2021 Jeep Cherokee on Jun 26, 2025
It’s a nice car, deceptively large inside, and comfortable. I’m average height but on the fluffy side, and it’s a very comfortable fit. Nice smooth ride. A/c feels like a freezer (I bought the car on the hottest day of the year and I was plenty cool on the long drive home.
Matthew P
Reviewed a 2021 Jeep Cherokee on Dec 29, 2024
The car’s features are awesome, all this at a great deal
John H
Reviewed a 2021 Jeep Cherokee on Nov 3, 2023
Great features and more than I expected. Great value for the money. Im very pleased with the SUV.
2021 Jeep Cherokee Trims
| Trim type | MSRP |
|---|---|
| Limited 4WD | $37,340 |
| High Altitude 4WD | $40,030 |
| North 4WD | -- |
| 80th Anniversary 4WD | $35,490 |
| Trailhawk Elite 4WD | -- |
| Sport 4WD | -- |
| Altitude 4WD | $32,895 |
| Trailhawk 4WD | $36,540 |
2021 Jeep Cherokee Price Trends
CarGurus tracks the prices of millions of used car listings every year. See how the average price of 2021 Jeep Cherokee prices has changed over time.
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