6. Jeep Cherokee – MSRP from $22,995
If you want the look and even some of the capability you get with the Jeep Wrangler, but you also want great on-road manners, the Cherokee is the affordable option. Of course the Grand Cherokee drives like a champion on and off the road, but the Cherokee provides plenty of road driving fun and trail driving utility for a much lower price. Some might find the outlandish design of the Cherokee strangely intriguing, while others might find it completely off-putting. The interior is also compelling, including a backseat with the most legroom available out of any compact SUV on the market today. The overall look and feel of the interior is markedly better than what you’ll find on other affordable Jeeps, making it a comfortable place to be for several hours while road tripping or driving to a rugged outdoor getaway.