Introduced for model year 2014 at the 2013 New York International Auto Show, sales began in November 2013.

[1][7] It occupies a position between the smaller Compass and the larger Grand Cherokee in Jeep's global lineup.

It includes seventeen-inch steel wheels, the Uconnect 5.0 touch screen radio, six speakers, cloth seating surfaces, a 2.4-liter Tigershark I4 engine, and nine-speed ZF automatic transmission.

An Altitude trim, derived from the Latitude, was introduced in spring 2014, which added black alloy wheels and blacked-out accents.

Other changes included a unique hood graphic, different bumpers for better approach and departure angles, wider fender flares, offroad skid plates and a full-size spare wheel.

The Limited served as the top-of-the-line model, and adds bright-finished alloy wheels, and leather seating surfaces.

Also included was the Uconnect Access 8.4A radio with an AM/FM stereo, SiriusXM Satellite Radio, iPod and USB input jacks, a 3.5-millimeter auxiliary audio input jack, hands-free calling, 9-1-1 Assist, Wi-Fi connectivity for wireless Internet access in the vehicle, wireless audio streaming, voice command, a full color touch-screen display, optional Garmin GPS navigation, and an optional single-disc player (mounted in the center console).

The Overland trim was discontinued following the 2020 model year, citing slow sales, as well as being similarly equipped to the Limited trim; however, the High Altitude Edition takes the Overland's place at the top of the Cherokee lineup for the 2021 model year.

Based on the Latitude trim level of the Cherokee, exclusive features included a Recon Green Metallic exterior paint color option, unique 75th Anniversary Edition exterior emblems, bronze-painted exterior accents, bronze-painted eighteen-inch (18") alloy wheels, premium cloth seating surfaces with "Ombre" mesh inserts and 75th Anniversary Edition embroidery, and bronze-accented interior trim.

The Uconnect Access 8.4A infotainment system, as well as a full panoramic power moonroof are both standard on this model, as is deep-tinted glass and automatic front head and fog lamps.

Jeep pushed back the release date of the Cherokee to allow time for the development of the nine-speed automatic transmission by ZF.

In late summer 2013, Jeep temporarily ceased production of its all-new Cherokee because of a transmission software issue.

In October 2013, a software fix was issued to the Cherokee, resuming production of the vehicle and shipment to dealers in the U.S. By November, the sales had started well in both the U.S. and Canada, with at least four weeks of stock depletion due to pre-order.

Chrysler stated on December 11, 2013, that the Cherokee advertisement campaign with the tagline Built Free was the most successful one since the introduction of the 2011 Dodge Charger.

To meet the demands of European buyers, the model was fitted with one or more diesel powertrains, most likely one or more versions of the FIAT Multijet engine with a displacement of 2.0-liter and 170 PS (168 hp; 125 kW).

The Belvidere Assembly facility did not have to be retooled in order to produce the Cherokee, and the production change took place after the Dart was discontinued following the 2017 model year.

[11] The Cherokee featured Chrysler's 2.4-liter Tigershark I4 engine that produced a maximum output of 187 PS (138 kW; 184 hp) and 232 N⋅m (171 lb⋅ft; 24 kg⋅m) of torque.

In select markets, FCA offered an all-new 2.2-liter Multijet II common rail direct injection turbodiesel with 185 PS (136 kW; 182 hp) or 200 PS (147 kW; 197 hp) and 440 N⋅m (325 lb⋅ft; 45 kg⋅m) of torque, achieving fuel economy of 49.6 mpg‑imp (5.70 L/100 km; 41.3 mpg‑US) combined.

The transmission yields approximately two additional miles per gallon with the V6 engine option compared to a six speed automatic.

However, Chrysler has been repairing some Cherokee models' transmission "snap ring" to address durability concerns.

[18] Multiple vehicles that use the same ZF model transmission, such as the Range Rover Evoque, Honda Pilot, Acura TLX, Chrysler 200, and even the similarly built Jeep Renegade have had issues of varying severity as well.

ZF has been quoted for suggesting that the issues were related to a faulty control sensor could cause the transmission to randomly drop into neutral while driving.

These transmission issues delayed the release of the all-new 2014 Jeep Cherokee KL to consumers until late summer 2014.

The restyled 2019 Jeep Cherokee KL made its debut at the 2018 North American International Auto Show in Detroit, Michigan, on January 16, 2018.

Engine choices for the 2019 Cherokee include the previously available 180-horsepower (182 PS; 134 kW) 2.4-liter Multi-Air inline four-cylinder (I4) and the 271-horsepower (275 PS; 202 kW) 3.2-liter Pentastar VVT V6 gasoline-powered units, though the V6 engine now came as standard equipment on the upper trim levels of the Cherokee, where it was previously optional.

Fiat Chrysler has released a television commercial for the restyled 2019 Cherokee for the U.S. market, entitled "The World Comes With It,"[22] which also appeared on the manufacturer's website for the vehicle.

The 2.4L Tigershark inline four-cylinder gasoline engine returned for the Altitude Lux trim as its sole engine option, while the Trailhawk gained the previously optional 2.0L turbocharged inline-four gasoline engine as standard equipment (both engines retained the ZF 9HP-based 948TE nine-speed automatic transmission), and both models were now only available with four-wheel drive.The Altitude Lux model gained a new Lux Elite Package that added the Jeep Memory System for the driver's seat, radio, and exterior side mirrors, a dual-pane panoramic power moonroof, a "hands-free" power rear liftgate; a 506-watt, nine-speaker Alpine premium surround-sound audio system with a subwoofer; a dual-pane panoramic moonroof; and heated and ventilated front seats.

A Sun and Sound Group for the Trailhawk model adds a 506-watt, nine-speaker Alpine premium surround-sound audio system with a subwoofer and a dual-pane panoramic moonroof.