Used 2020 Jeep Cherokee for Sale near Winnipeg, MB
33 results
CarGurus Analysis:
2020 Jeep Cherokee
With 33 currently listed for sale near Winnipeg, MB and an average price of $21,122.00 CAD, 27.3% of 2020 Jeep Cherokees for sale on CarGurus are rated as good or great deals.
Favourably reviewed: Owners rated the 2020 Jeep Cherokee 4.77 / 5 stars.
100.0% of 2020 Cherokee models on CarGurus are accident free.
The 2020 Jeep Cherokee is praised for its strong performance, comfortable ride, and spacious interior, with many drivers favouring the V6 engine for its power and smooth handling.
CarGurus Analysis: 2020 Jeep Cherokee
Summary
With 33 currently listed for sale near Winnipeg, MB and an average price of $21,122.00 CAD, 27.3% of 2020 Jeep Cherokees for sale on CarGurus are rated as good or great deals.
Favourably reviewed: Owners rated the 2020 Jeep Cherokee 4.77 / 5 stars.
100.0% of 2020 Cherokee models on CarGurus are accident free.
The 2020 Jeep Cherokee is praised for its strong performance, comfortable ride, and spacious interior, with many drivers favouring the V6 engine for its power and smooth handling.
Why it stands out
The 2020 Jeep Cherokee distinguishes itself with a blend of performance and comfort, making it a popular choice among compact SUVs. Its V6 engine option provides robust power, appealing to those who value a spirited driving experience. The interior is spacious and well-equipped, catering to families and individuals alike. Additionally, the Cherokee's off-road capabilities remain a hallmark of the Jeep brand, allowing it to tackle various terrains with ease. While some users have noted a lack of quick acceleration and dissatisfaction with certain features like the auto-stop function, the overall consensus is that the 2020 Cherokee offers a well-rounded package for both daily driving and adventure.
Other model years to consider
- Average price: $24,685.00 CAD
- Good/great deal percentage: 29.4%
- User rating: 4.8 / 5
- Total listings: 34
- Average price: $19,433.00 CAD
- Good/great deal percentage: 29.2%
- User rating: 4.67 / 5
- Total listings: 24
- Average price: $15,999.00 CAD
- Good/great deal percentage: 20.0%
- User rating: 4.8 / 5
- Total listings: 20
This analysis is based on CarGurus' proprietary market data from July 15, 2026, CarGurus experts' opinions, and generative AI.
4.8 Overall rating
Filter by rating
Michael W
Reviewed a 2020 Jeep Trailhawk Elite 4WD on Jul 29, 2024
The vehicle is very capable on and off road. Plenty of power to get up to speed on the highway, pass someone, and 4500lb towing capacity. Also it is the only trailhawk in the lineup to have a true rear locker.
Amanda W
Reviewed a 2020 Jeep Cherokee on May 5, 2025
This is a great vehicle. It has every feature that I asked for & more. It will have no issue towing my camper or hauling my kayaks.
Steinar A
Reviewed a 2020 Jeep Cherokee on Mar 10, 2023
I am.... impressed with the 2020 Jeep Cherokee Trailhawk. Specifically, the non-elite version has less fluff and is less likely to need repair amongst the electronics (no panorama roof, no rear tailgate motor, no advanced controls such as advanced cruise control, no heated seats or heated steering wheel & no NAV - etc. It does what it is supposed to do. I am also averaging 28 mpg versus the listed 24 mpg. I also added Falken Wildpeak ATW/3 tires to it (which makes it a better off road vehicle) also. Im pleased as punch with this Cherokee. Its a shame that Stellantis (Chrysler/Jeeps parent company) did not support this line of vehicles for the past 2 years & shut down the Belvidere plant (20 miles away from me) last month. There is zero reason why Stellantis cannot make money on this line of vehicles.
Douglas B
Reviewed a 2020 Jeep Cherokee on Jun 28, 2022
The only thing I dont like about the 2020 jeep Cherokee is the power. It lacks the take off power I prefer. But other than that its a beautiful vehicle rides smoothly and is comfortable.
2020 Jeep Cherokee Trims
| Trim type | MSRP |
|---|---|
| High Altitude 4WD | $36,840 |
| Overland 4WD | $38,495 |
| North 4WD | $31,800 |
| Altitude FWD | $28,790 |
| Sport 4WD | -- |
| Limited 4WD | $34,845 |
| Trailhawk Elite 4WD | $37,950 |
| Trailhawk 4WD | $34,755 |
2020 Jeep Cherokee Price Trends
CarGurus tracks the prices of millions of used car listings every year. See how the average price of 2020 Jeep Cherokee prices has changed over time.
See more price trendsFAQs
How much does the 2020 Jeep Cherokee cost in Winnipeg, MB?
How many 2020 Jeep Cherokee vehicles in Winnipeg, MB have no reported accidents or damage?
What is the fuel economy of the 2020 Jeep Cherokee?
What fuel types are available?
Relevant articles
Best Small SUVs in Canada for 2026
Small SUVs are hugely popular with Canadian buyers thanks to their practicality and versatility. Here's our pick of the best.
Jeep Cherokee Buying Guide: Cost, Reliability, and the Best Years to Buy
Our definitive Jeep Cherokee buying guide covers the history and specs of each of the four model generations, how much you can expect to pay for one, and which are the best and worst versions to buy.
2026 Jeep Cherokee: Price, Specs and Release Date
The Cherokee competes in the compact class, offering a unique and more rugged take on the segment that sets it apart from the sea of mostly alike competitors. Jeep fully redesigned the Cherokee for the 2026 model year.
